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Olive Vacation Rentals

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    All 63 Rentals in Olive
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    The following rentals are within 10 miles of Olive.
    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 41
    (4)Excellent
    Woodstock
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Sanctuary by the Stream - close to ski centers - lower winter prices in effect1 / 23
    (17)Excellent
    Phoenicia
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming Artist's Cottage1 / 18
    (71)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Komorebi - Cozy 2BD Guest House in the Forest1 / 19
    (9)Excellent
    Chichester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2017
    If there's anything you can immediately take from my review, without reading further, it is this: the place was fantastic to stay at.I emailed Karin because I wanted to know...
    Reviewed June 14, 2017
    Great stay at this beautiful home in the woods! The house is a short drive from Phoenicia and about 20 minutes from Woodstock. We got our chance to do a little souvenir shopping...
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    About this property
    Our 2 bedroom, 2 floor guest apartment is extremely cozy and has all you need for a quick getaway. You will have your own private keyed entrance opening into your own living room and small kitchenette (refrigerator, microwave, coffee maker, plates, bowls, glassware, silverware, etc). Upstairs you...
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    Chichester, Catskill Region 12416
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Spend Xmas at Pet Friendly Cabin Doh-Ray Up At 1450ft!1 / 30
    (6)Excellent
    Woodstock
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Porch
    • Central Heating
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 24, 2017
    The cabin is comfortable and well equipped. The grounds are well kept and lovely. There is easy access to Woodstock and other towns. We were there when the weather was hot...
    Reviewed November 15, 2014
    My family and I wanted to get away from all the noise and hectic schedule of our everyday lives. Cabin Doh-Ray was the perfect home away from home. The cozy house had all the...
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    About this property
    Pet Friendly Cabin surrounded by the forests of Mt. Guardian at an altitude of 1500 feet. 3 Day Minimum Christmas. + Large summer porch overlooks a beautiful pond + Stays cool in the summer (has only reached the 90s two summers in the last 10 years) + Beautifully furnished + Pine...
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    Woodstock, Catskill Region 12409
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 64
    (7)Excellent
    Woodstock
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 17, 2017
    Fern Hollow is an absolute gem. From the minute you step into the home you’ll be embraced by very intricate detail followed by beautiful wooden furniture (some appears to be...
    Reviewed December 2, 2017
    It’s hard to describe the amazing time we had staying here. It was an escape, a retreat, an adventure, a delight. To most, the timing of our stay might seem odd. Neither summer...
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    About this property
    Luxurious 3 BR / 3 BA, handmade craftsman style home, in the heart of Woodstock! Pamper yourself with a private pool, spa and stream. Enjoy serenity and privacy, as this property is located on 7 acres, at the end of a private road, yet is still only 5 min to the heart of town. Tastefully...
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    Woodstock, Catskill Region 12498
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Woodstock Cottage: walk to Town1 / 22
    (3)Excellent
    Woodstock
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Secure Parking
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2017
    We've stayed at this beautiful property three times already. The house has 2 full bedrooms and baths, a spacious and well-equipped kitchen, electric fireplace, gas grill, etc...
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    About this property
    WALK TO EVERYTHING IN THE VILLAGE FROM THIS NEWLY RENOVATED COTTAGE WITH GORGEOUS VIEWS! Located in the center of the village, this newly renovated cottage is open, cozy, and perfect for a Woodstock vacation or weekend getaway. Convenience is the name of the game here. No vehicle is necessary....
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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Woodstock In-town cottage1 / 23
    (45)Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    • Hot Tub
    • Mountain Views
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 22, 2016
    Ellen could not have been more accomodating or gracious a hostess. She met us in the parking lot, saving us a spot - all smiles and happy energy. She put some basic...
    Reviewed October 31, 2016
    The cottage is located right in the center of town, yet it is entirely secluded. It is extremely quiet and you feel like you're in your own little world. The cottage was...
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    About this property
    Located right in the middle of Woodstock, this recently renovated cottage with a cozy, open floor plan affords you both privacy and convenience. There's no need for a car. Walk to everything, including the NYC bus stop, Woodstock's unique shops and galleries, or hiking trails. Cook your own meals...
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    Woodstock, Catskill Region 12477
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Woodstock Cabin in the Woods1 / 9
    (8)Excellent
    Willow
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Yard
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Sauna
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 31, 2017
    Rainy days in the woods....Perfect place to snuggle! We brought the city dogs and they loved trekking around woods. Babbling brooks and critters behind the cabin. Artistic town...
    Reviewed May 1, 2017
    The hosts shared with us their camps on their property, it was a perfect set-up. The area is really peaceful. The camp is very comfortable, relaxing and smart. We were their to...
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    About this property
    Relax and enjoy yourself in one of our two beautiful, hand crafted log cabins, located on a wooded mountainside. You will experience the peaceful inspiration of the Catskill Mountain Wild Forrest. Starry nights, fresh air and birdsong await and some nights there might be a giant bonfire to enjoy...
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    Willow, New York 12495
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Romantic Country Barn By the Stream1 / 26
    (17)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Hot Tub
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2017
    Very nice, clean, pet friendly cottage. Owner was very accommodating and flexible when we had to change our rental date. Home is fully stocked with everything you would need...
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    About this property
    Nestled between two streams, a large, cozy private barn, on five acres of wooded land, and large lawn. A smaller stream just outside your window. Comfortable, with modern accommodation and beautiful artistic details. A perfect place for a peaceful romantic getaway, soak yourself in the outdoor...
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    Location Information
    Woodstock, Catskill Region 12457
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chichester
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Central Heating
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet country home on a stream in the Catskills, a short weekend trip from NYC. A wall of windows looks over the stream. The kitchen is large and well-equipped. Three bedrooms, two baths, and a fireplace make this retreat great for families, girls' weekends, retreats, and ski getaways. Relax at...
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    Chichester, Catskill Region 12416
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Woodland Valley Retreat-beautiful mountain cottage1 / 42
    (4)Excellent
    Phoenicia
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Grill
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 18, 2017
    I booked the cabin as part of a long-weekend getaway for myself, my husband, and another couple. I would book again the next time I need some R&R.Greta was a wonderful host...
    Reviewed October 16, 2016
    This was such a great place to stay for a weekend getaway. Absolutely beautiful, clean, homey, and fun! The nearby town is adorable!
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    About this property
    Contemporary-style one family home with large deck offers: • Fully equipped kitchen • Large living and dining area • Spacious outdoor deck with picnic table and bbq • Spiral staircase to roomy master bedroom • Additional sleeping arrangements available in a loft over the kitchen and 1 single...
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    Phoenicia, Catskill Region 12464
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Secluded, Luxury Home with Hot Tub1 / 19
    (9)Excellent
    Woodstock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • DVD Player
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 8, 2017
    Mirav was very responsive and friendly. The house was perfect and had everything you needed. The hot tub was a very nice addition as well. My hubby and i had a very relaxing...
    Reviewed March 1, 2017
    this place is perfect. the house has all the amenities you will need, its warm and welcoming. the owners were very communicative. its close to both Woodstock and Saugerties. we...
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    About this property
    On the border line of Woodstock & Saugerties. 4.5 miles from the center of Woodstock village. Drive down a private country road to Saddle Hill where you will find a completely secluded retreat nestled, on 2.5 acres, between the Catskill Mountains and rolling fields. Beautifully renovated, spacious...
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    Woodstock, Catskill Region 12477
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Romantic and Luxurious Spa Loft in the Treetops1 / 23
    (3)Excellent
    Phoenicia
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Terrace
    • Mountain Views
    • Parking
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 6, 2016
    Loved this loft. warm & quiet in the winter, walking distance to food and drinks, beautiful views of the mountains. Spa styled bathroom was amazing and very relaxing! i...
    Reviewed September 29, 2015
    The location was perfect & so were the accommodations. Really a beautiful loft right in the middle of everything you need to be in the middle of. A 2 minute walk to the center...
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    About this property
    The Phoenicia Loft is situated in the tiny village of Phoenicia in the heart of the Catskills only 10 minutes from great skiing at Belleayre Mountain. Nestled between Mount Tremper and the mighty Esopus River, it is an eclectic mix of old world comfort and super modern European luxury. With it's...
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    Phoenicia, Catskill Region 12464
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Woodstock Secluded MT Top Home with  Swimming pool1 / 18
    (4)Excellent
    Woodstock
    6 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 8, 2015
    The Pictures of this Glorious....Peaceful Place does not do it justice as too how Stunning it truly is......The house was Immaculate......The Swimming Pool was not just inviting...
    Reviewed July 29, 2015
    I don't often right reviews but I really wanted to share with everyone how wonderful this location is. This is our third year renting homes as a family of 15 and this house was...
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    About this property
    This home has 3600 sq ft of space 6 bedrooms, 3 baths, an extra sunroom that can be used as another bedroom and can accomodate a group of 12-15 or an average size family . Though it is very private on 15 acres its just 1 and half mile to the center of Woodstock.The village of Woodstock has many...
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    Woodstock, Catskill Region 12498
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 15
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    Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts1 / 21
    (1)Excellent
    Woodstock
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Housekeeping Included
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *****PLEASE SEE THE PAGE WITH ALL DETAILS JANNA RITZ DOTT COME****quintessential woodstock stone cottage with original large 11 ft artist window and stone fireplace. completely gutted and new everything but with cottage flair. new kitchen huge thermador pro range, baths, plumbing, electric,...
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    Woodstock, Catskill Region 12457
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    . This is an 1870's post and beam barn. For 20 years, before we owned it, the barn was a Montessori school. After we purchased the property, we converted the school to a guest cottage. The hand hewn beams you see in the photos are preserved in their original condition, as are the hardwood...
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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Phoenicia
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Best location in town! Your perfect all season escape. Our spacious home comfortably accommodates up to 10 guests. Just a short stroll to Phoenicia's charming restaurants and specialty stores. Our property is next to the Phoenicia Parish Field which accesses miles of beautiful trails through...
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    Phoenicia, Catskill Region 12464
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cozy & Serene Cottage in Woodstock1 / 13
    (3)Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Housekeeping Included
    • Patio
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2017
    V's place was cozy, clean, and very quiet. The deck was our favorite! Lovely spot to sit and enjoy the country -- especially the outstanding view of Overlook Mountain. It was...
    Reviewed June 29, 2017
    Fascinating artistic community with unique shops, great restaurants and beautiful mountain vistas.This was my first trip to Woodstock and I can’t wait to come back to the...
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    About this property
    Cozy, clean & light-filled cottage designed for all-season comfort, relaxation & rejuvenation set on serene landscaped grounds & woods. Cottage is perfect for romantic weekends, country getaways, or solo retreats. Dreamcatcher is unique. The cottage sits on a beautiful 4.5 acre property but is less...
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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Catskill Clean Comfortable Close1 / 17
    (1)Very good
    Shokan
    3 Bedrooms, 1 Bathroom, Sleeps 11 Quick View
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    • Mountain Views
    • Parking
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Yard
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2017
    We booked this accommodation for a weekend in fall with 7 adults and had a perfect stay. Our expectations were met in full: the cabin is truly what whe had in mind for a cosy...
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    About this property
    Its nothing special, just a 1960, 3 bdrm 1 bath brick ranch in a quiet neighborhood. 17 acres with year round stream. Very clean, well equipped kitchen w/ great outdoor party areas w/fire pit. I have comfortable seating for 11 guests in the living room. 10 minutes to Woodstock & Phoenicia just...
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    Shokan, New York 12481
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 11
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    Woodstock
    50 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Yard
    • Parking
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally built in the 1870's as a small barn on the estate. The cottage was fully renovated, new bath, new kitchen, refinished hardwood floors, pillow top mattress in the sleeping loft, and a queen size Murphy bed if you prefer not to use the sleeping loft. This is a petite one room studio...
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    Woodstock, Catskill Region 12498
    Rental Home - 50 Bedrooms, 1 Bathroom, Sleeps 4
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    Woodstock Retreat, Sauna, Steam Shower, Decks1 / 22
    (1)Very good
    Woodstock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 30, 2016
    The accommodations were very comfortable even with 3 kids. Location was very private with lots of skylights and scenic views. We enjoyed the sauna and steamy showers and...
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    About this property
    Restore yourself at this lovely vacation home while you explore Woodstock, the Hudson Valley and the Catskills. You will be surrounded by woods, mountains and hundreds of acres of public land, and visited often by deer and turkeys -- but you are 10 minutes from the center of Woodstock, a lively,...
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    Woodstock, Catskill Region 12495
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coldbrook B&B 2 hours North of NYC Woodstock, NY1 / 16
    (1)Excellent
    Woodstock
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Wi-Fi
    • Mountain Views
    • Parking
    • Cable/satellite TV
    • Outdoor Dining Area
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2015
    We found this B&B through a friend and were so pleased with our visit we will be back as often as our host, Mark, will let us! This is the perfect place to get away from it...
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    About this property
    Coldbrook B&B is exclusively a Bed & Breakfast and located 2 hours north of New York City in the heart of the Catskill Mountains and 10 minutes to the center of famous Woodstock, NY. Peace and quiet are abundant with the option to peruse the charming shops in the quaint and artsy town of...
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    Woodstock, Catskill Region 12409
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Margaret's Cottage in Woodstock Village1 / 22
    (3)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Patio
    • Grill
    • Cable/satellite TV
    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2016
    Nice owners who have been living in the area for years gave us everything we needed. Pantry was well-stocked. They gave us their bbq gas when ours ran out mid-cooking!
    Reviewed August 29, 2015
    I stayed here with my mom and my 4-year-old son. Mary helped to make the visit perfect for all three generations. She set up a wading pool and fire pit in the beautiful back...
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    About this property
    Margaret's Cottage Located the in the village of Woodstock , stroll to restaurants, Tinker St movie theater, take a dip in the Millstream, or follow the Comeau trail past the steam through the woods to the meadow with the best mountain vista in town. On the NYC bus route Two bedroom cottage ,...
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    Woodstock, Catskill Region 12498
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Shokan
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience peace and tranquility in a newly renovated downstairs apartment in a barn home located at the end of a mountain road in the Catskill Watershed with views, fishing , boating, hiking, 10 minutes from Woodstock. Considered by locals as one of the best locations in the Catskills. Beautifully...
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    Shokan, New York 12481
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 82
    (3)Excellent
    Woodstock
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 2, 2017
    Very clean,spacious and relaxing house ! enjoyed every moment staying there.!Owner was very friendly and responsivw when needed. definitely will come again soon !!!!
    Reviewed May 30, 2017
    We rented this house for a long weekend -- several adults and a few babies included. Our travel time from Brooklyn was a little over 2 hours, so it's a great getaway that's not...
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    About this property
    Welcome to Woodstock! This spacious 5 bedroom/3 bathroom home features wide open spaces, a master bedroom with an en suite bathroom, an in ground pool, and game room with a ping pong table, a toasty wood stove for chilly nights, and all the benefits of being a two to three minute drive from...
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    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Orange Door Retreat1 / 10
    (1)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a two bedroom modern house on a small hill. The location is perfect, walking distance to downtown Woodstock, easy access to community swimming holes, town events, galleries, shops & restaurants. You can enjoy the peace and quiet in the woods, and only 10 minutes walking, you are in the...
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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A Little Woodstock Love Nest. Walk to everything!1 / 17
    (1)Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed July 10, 2016
    Lovely apartment very close to all the quirky shops, delicious delis and fabulous bars/restaurants in Woodstock.Extremely comfy and clean with everything you would need for your...
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    About this property
    Your new place to stay in Woodstock! Romantic 1BR right on Tinker Street a short stroll from Woodstock's amazing restaurants, galleries and specialty stores. No car required- Bus from NYC drops you within three minutes walk from our front door. Hiking, skiing, swimming close by. .Lovely one...
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    Woodstock, Catskill Region 12498
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Cottage at Chichester1 / 14
    (23)Very good
    Chichester
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Mountain Views
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 29, 2017
    We love this place. We have stayed at this cottage three times now, and each time has been wonderful. The place is clean and very comfortable, and the surrounding area is...
    Reviewed August 22, 2017
    Great location, close to hiking and restaurants in Phoenicia. The property is lovely. It has a private picnic spot and private access to the Esopus for lounging in the sun and...
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    About this property
    This Catskills Vacation Cottage is located on three acres, 3.4 miles North of Route 28 on Route 214, about 2 hours from NYC. The Catskills vacation rental is nestled between two mountains with the Stony Clove Creek at the rear of the heavily wooded property. Conveniently located, it's just 10...
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    Chichester, Catskill Region 12416
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Zen den1 / 12
    (6)Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 11, 2017
    Very relaxing and quiet spot, the place was very clean an welcoming from the second we walked through the gates.
    Reviewed September 24, 2017
    Zen Den was a peaceful, beautiful setting-- harmonious, clean, convenient to town. My son and I loved our time together there, and I look forward to bringing my daughter for...
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    About this property
    Welcome to the Zen Den! Enjoy our beautiful, newly constructed, 2 story apt 60 seconds from the heart of town. Free parking, covered porch in the expansive back yard, full kitchen, full bathroom, BBQ, perfect for enjoying your stay in Woodstock! Enjoy this sweet and cozy retreat IN TOWN. Located...
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    Woodstock, Catskill Region 12498
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Woodstock Mediterranean Retreat1 / 26
    (3)Excellent
    Woodstock
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Grill
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    • Washer
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    Ayanna's meditaranian retreat was an amazing experience. The house is beautiful all of our needs were met, very clean and nicely decorated we felt so at home. The heated salt...
    Reviewed August 18, 2017
    My family and I stayed 5 nights. We had a great time, the house is beautiful and it's spacious. We were 5 adults and 3 children and we all had our own space. The house is...
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    About this property
    Say hello to your perfect vacation home! Bright and airy Woodstock home with all the amenities you will need. Located only 4 minutes from the Village of Woodstock. Four-bedroom house with 3 full bathrooms located on private roadway perfect for walking & running around neighborhood. The house...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Woodstock Village  Serene &  Spacious1 / 10
    (5)Very good
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2016
    I highly recommend Woodstock Village Serene & Spacious. This was my second stay there and I love it! The location is perfect and the owner keeps the place immaculate. The...
    Reviewed June 29, 2016
    This stay comprised one house divided into two. Our cottage was Citrus the other Plum. Ours was on the darker side which was good in summer as it was hot. But Plum would have...
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    About this property
    Choose from two newly renovated private two bedroom suite/deplex apartments ( Citrus and Plum) in a turn of the century country Victorian designed to make your stay in Woodstock memorable. Unplug and leave your worries behind. You can walk to all destinations on Tinker Street. It is a 5 minute...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Glenford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 2 hours North of NYC & 5 miles from Woodstock NY- The Glenford House offers 3 bedrooms, 2 full baths, sleeps 6-8. Hot Tub, outdoor fire pit, ping-pong table, fireplace, gas grill, deck with amazing views. Good cell phone reception and wifi. Sorry, no pets. Experience the serenity and...
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    Glenford, Catskill Region 12433
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Woodstock
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to 'Casa Reál,' an exquisite 4-bedroom, 4-bathroom Spanish-style vacation rental house in Woodstock, New York, with accommodations for 8. This wonderful ranch home is ideally situated on a semi-private lot with scenic tree views and a private hot tub, mere minutes from town, surrounded by...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Mount Tremper
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover life in the Hudson Valley from this expansive 3-bedroom, 2-bathroom Mount Tremper vacation rental house, which sleeps 6 comfortably. Featuring state-of-the-art amenities, lush forest views, free WIFI, and a peaceful, secluded location, this home represents everything that is great about...
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    Location Information
    Mount Tremper, New York 12457
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    --------Authentic 18 foot Sioux Tipi, handmade and painted by the artists at Nomadics Tipi Makers in Oregon. The tipi overlooks a waterfall on the Sawkill Creek that runs through our estate. Across the river is Comeau Park, with a 2 mile walking trail. The center of Woodstock Village [and...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Woodstock
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This special home is a converted barn with the original 1790's foundation. We want our guests to feel at peace and have a relaxing vacation! The house is filled with unique collectibles and folk art. You'll find an eclectic collection of original paintings throughout the house. Each room has a...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Garden Cottage In The Catskills1 / 43
    (3)Excellent
    Chichester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 22, 2017
    This place is absolutely lovely. I stayed here for one night with three friends and we had a blast. There was enough space for all four of us without feeling cramped- one on the...
    Reviewed September 6, 2017
    This is a charming cottage with wonderful owners. We picked our own garden vegetables, slept in the cozy loft to the sound of the rain, and had a campfire under the stars...
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    About this property
    Welcome! Our newly renovated cottage sits among flowering gardens, across the road from a lovely stream, just 2 miles from the village of Phoenicia & minutes away from the ski slopes. The cottage is filled with artwork from around the globe and every corner is a pleasure! We have lovingly...
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    Location Information
    Chichester, Catskill Region 12416
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bearsville Retreat Fireplace, Hot tub & Pool1 / 45
    (13)Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2015
    My husband and I escaped from the city to The Bearsville Retreat for a weekend and could not have been happier with the home. Everything was pristine, but cosy enough to feel...
    Reviewed October 6, 2015
    My husband and I spent a week with another couple at this blissful compound, just down the road from the town of Woodstock, NY. They stayed in the main house and we were in the...
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    About this property
    Charming house In a compound consisting of of two houses in the green rolling hills of Bearsville. It is 5 mins to Woodstock Village Green. Heated, saltwater pool, hot tub, fireplace. Renovated in a relaxed lodge style. Local Spa 5 mins away to relax your mind spirit and body. Come and...
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    Location Information
    Woodstock, Catskill Region 12409
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lake Hill
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful mountain views on 6.5 acres a few miles from Woodstock, NY. This homestead features 3 bedrooms, 2 bath in Lake Hill. Nightly, weekly or monthly rental available. Great for those seeking seclusion and privacy. Outdoor jacuzzi, pool. Great for ski season. House can sleep up to 6 people....
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    Lake Hill, New York 12448
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stunning Vacation Country & Ski House1 / 23
    (3)Excellent
    Woodstock
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
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    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 2016
    We had a great time. It's secluded so no worries about bothering the neighbors. House was very clean. Kitchen is fully stocked. We spent the whole weekend on the shaded back deck.
    Reviewed November 4, 2013
    My friends and I went there for a relaxing birthday weekend and that's exactly what we had! The house is super private and beautiful! We had a blast! We didn't even leave the...
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    About this property
    This NON SMOKING country home is privately nestled within 15 unspoiled wooded acres overlooking picturesque seasonal trout stream. With sunny, open floor plan the open kitchen / living room / dining room make for great family together time. High quality appliances, comfortable furniture and...
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    Location Information
    Woodstock, Catskill Region 12463
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Woodstock
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable and spacious family home (2,500sq ft) has four bedrooms upstairs and plenty of socializing space downstairs including a screened in porch, deck & bbq, a great room, playroom, fireplace room, surrounded by 80 ft pine trees and a level lawn. This spacious home, 5 mins drive into...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Bearsville
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Housekeeping Included
    • Hot Tub
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our house In the Woodstock hamlet of Bearsville. It has been lovingly renovated (renovations completed In 2015) and has a clean, modern and updated feeling from the new renovations, but retains much of its original charm and original farmhouse detail. We fell in love with the location...
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    Location Information
    Bearsville, New York 12409
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Woodstock
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1964, this classic mid century modern boasts its original kitchen cabinets as well as a wall of Danish storage units in the living room. It comfortably sleeps 8 in its 5 air conditioned second floor bedrooms, all of which have access to the balconies on both sides of the house. The master...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    Bearsville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Porch
    • Private Outdoor Pool (Heated)
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely gutted out and renovated and just completed! one week ago.....this fantastic warm and inviting modern country home, has so much light.......the interior brings in the green from outside all over..... amazing open loft design, with fantastic cooks kitchen and island for gathering...its a...
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    Location Information
    Bearsville, New York 12409
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    charming woodstock cottage with outdoor hottub1 / 14
    (1)Excellent
    Willow
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful well-kept cottage on Silver Hollow Road. Available weekends or weekly. 1 +1/2 bedrooms, ( queen size loft sleeping area ) . Very private. Large outdoor hot tub for 6. Located near all local ski areas and hiking trails. $465/weekend ( 3 days 2 nights, includes cleaning ), or $ 1175...
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    Location Information
    Willow, New York 12495
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Woodstock
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ”. The home is a classic saltbox contemporary and sits on approx. 5 private acres. The area is dotted with waterways and rock outcroppings that are part of the local landscape. This is a beautiful time of year to be here. The summer months are special and the area has a wonderful assortment of...
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    Location Information
    Woodstock, Catskill Region 12401
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sunny, Peaceful Catskill Mountain Hideaway1 / 10
    (2)Excellent
    Mount Tremper
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Terrace
    • Parking
    • Balcony
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    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2017
    Need to get away from it all? Stay here.* Just 17 minutes away from Woodstock (quaint town with shops, restaurants) * Cozy cabin is accurate to pictures online - what you...
    Reviewed January 5, 2016
    Brent and Wendy were amazing hosts. From the very beginning, Brent worked with our arrival schedule and made us feel so very welcome. Once we arrived, the cabin was more than we...
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    About this property
    Please read property description completely before booking. Escape all your worries in this quiet, cozy, newly-renovated studio retreat in the Catskill Mountains of New York. It offers a comfortable balance of rustic and elegant, located midway between lovely towns, Woodstock and Phoenicia. Queen...
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    Location Information
    Mount Tremper, New York 12457
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Woodstock New York--- Sunset cottage is an award winning vacation home. This home has been featured in NY Magazine and architectural Digest It is fully furnished, has a completely equipped stainless steel kitchen, wifi, cable TV DVD, AC & HEAT, tile bathroom with tub & shower, hand hewn beams,...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Phoenicia
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Yard
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house surrounded by mountains and creeks in the nature on a cute quiet street in the friendly town Phoenicia, Catskills. It's unique because it's private, NOT on a busy main street or highway... and yet so conveniently located that's within 5 mins walking distance to the town for restaurants,...
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    Location Information
    Phoenicia, Catskill Region 12464
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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