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Woodstock House Rentals

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    Travelers to Woodstock are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in WoodstockView all 39 rentals
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    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 62
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 89
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Charming Artist's Cottage1 / 18
    (69)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Housekeeping Included
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    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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    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 41
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
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    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2016
    The house is beautiful, interesting, spacious, and cozy, with so many different places to sit, gather, read, perfect for our group of 8 consisting of 3 generations including 4...
    Reviewed June 23, 2016
    Nestled appropriately on a street called Holiday Street, Casa Real was a homey vacation rental for our family of 7, some of whom travelled from India for this staycation. a 15...
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    About this property
    Welcome to 'Casa Reál' this Spanish style ranch is tastefully decorated with mid-century modern furnishing. It's got large open spaces, good flow and contemporary floor plan. This home also features a sunken living-room, formal dining room, sunken family room with wood-burning fireplace and a large...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts1 / 21
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Cable/satellite TV
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    • 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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    Pet Friendly Cabin Doh-Ray Up At 1450ft1 / 30
    (6)Excellent
    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
    • Internet Access
    • 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. + 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 & bluestone floors +...
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    Woodstock, Catskill Region 12409
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Woodstock Secluded MT Top Home with  Swimming pool1 / 9
    (4)Excellent
    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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    Secluded, Luxury Home with Hot Tub1 / 19
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Location Information
    Woodstock, Catskill Region 12477
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stunning Vacation Country & Ski House1 / 23
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Porch
    • Internet Access
    • Patio
    • Central Heating
    • Grill
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Salutations from this sunlit, solar powered house with mountain views! We are little over a mile to the village green/Woodstock central! Four bedrooms (two master suites) sleep eight comfortably, with one king bed, two queens and two twin beds (ACs in each bedroom in the summer). Two and a half...
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Woodstock Village  Serene &  Spacious1 / 10
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
    • Porch
    • Washer
    • Outdoor Dining Area
    • Cable/satellite TV
    • Internet Access
    Suitability
    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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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Woodstock Mediterranean Retreat1 / 26
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    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 Retreat, Sauna, Steam Shower, Decks1 / 21
    (1)Very good
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Parking
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    • Patio
    • DVD Player
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    Suitability
    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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    Woodstock, Catskill Region 12401
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • 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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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Woodstock Farmhouse Mountain Views and Hot Tub1 / 13
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Reviewed July 19, 2015
    We spent the long weekend of July 4th in the farmhouse. Very well maintained and furnished, lot of room for the 9 of us including 4 children. The spa was a big hit with the kids...
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    About this property
    Newly built 3-story cedar Farmhouse sleeps 9, secluded on 5+ acres of wooded land surrounded by mountains, mature trees and wildflowers. Finely decorated with antiques in bright airy rooms and pine wood floors. Every window has amazing views of nature yet The Woodstock Farmhouse is only an 8 minute...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Orange Door Retreat1 / 10
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Internet Access
    • Parking
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    Suitability
    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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    Bearsville Retreat Fireplace, Hot tub & Pool1 / 45
    (13)Excellent
    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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    Woodstock, Catskill Region 12409
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Patio
    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    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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    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    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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    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    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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    Olive Oasis Luxury with Hot Tub, Woodstock Area1 / 52
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 11, 2017
    Enjoyed a weekend break here. Beautiful isolated location. Accommodation quite tired looking and very basic especially for the price paid.
    Reviewed September 18, 2014
    The place is as nice as promised, with the hot tub, grill, entertainment center, all in good working order. My only caveat, is that this rental is best for 2 couples. The...
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    About this property
    The perfect getaway for family and groups, artists, writers, yoga and meditation lovers all are welcome. Escape to a magical land- private and secluded with a hot tub out door, relax, hike, ski, meditate or create your new masterpiece. The place invoke your imagination and stimulate your...
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    Location Information
    Woodstock, Catskill Region 12481
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 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
    This charming English Tudor Carriage House is the perfect retreat and located in a wooded setting on 10+ acres on a wooded estate only 1.5 miles to the center of Woodstock. It is a spacious 4 bedroom, 1 1/2 bath home with a lovely stone fireplace. The Carriage House is nestled at the foot of...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two miles from the center of the renowned artist colony of Woodstock, New York, a long driveway off a peaceful country road leads you to the grace and charm of this turn of the century farm house.Set amidst acres of rolling meadows and magnificent pines, encircled by the Catskill Mountains, the...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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