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Woodstock Rentals for Seniors

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    Travelers to Woodstock are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    36 Matching Rentals in WoodstockView all 135 rentals
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    Got Renovated Modern Home in Prime Woodstock w/ Heated Pool1 / 80
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 31
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Woodstock Cottage: walk to Town1 / 22
    (1)Excellent
    2 Bedrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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, 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
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    • Grill
    • Hot Tub
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    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 Secluded MT Top Home with  Swimming pool1 / 9
    (4)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
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    • 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 In-town cottage1 / 23
    (44)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Air Conditioning
    • 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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    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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    Aspects Inn & Spa --A Sensual Retreat in Woodstock1 / 13
    (12)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Sauna
    • Mountain Views
    • Internet Access
    • Satellite TV
    • Private Indoor Pool
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2015
    What a wonderful get away. Thank you to Lio and Sharon for providing such a wonderful retreat! The spa area was absolutely perfect and afforded us a truly relaxing and...
    Reviewed April 15, 2014
    My husband and I were in need of a relaxing and quiet getaway. Aspects Inn and Spa seemed like a great choice. This stay surpassed all our expectations. The apartment is clean...
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    About this property
    Aspects Inn & Spa in the heart of Woodstock, NY offers a unique retreat with a two apartment 2 bedroom each w/ full kitchen and all amenities with direct access to our indoor spa with 40' saline pool, ionized Jacuzzi and infrared sauna. at the rate of $250 per night 1 couple...
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    Woodstock, Catskill Region 12498
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Yard
    • Secure Parking
    • Wi-Fi
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    • Satellite TV
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aspects Inn and Spa! Lio and Sharon invite you to their Aspects Inn and Spa in the heart of the historic artists colony of Woodstock, NY. Nestled in the gentle streams and valleys of the ancient Catskill Mountains, Woodstock is just a two hour scenic drive up the thruway from NYC or a...
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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Patio
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Parking
    • Wi-Fi
    • Patio
    • DVD Player
    • Private Yard
    • Satellite TV
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    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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    Zen den1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2017
    First time in Woodstock. Perfect location! Park and walk to everything. And yes it is 1 minute to the main strip! If you want a peaceful serene get away from the stresses of...
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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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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Housekeeping Included
    • Grill
    • Secure Parking
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    IDEAL LOCATION FOR UPSTATE NEW YORK, WOODSTOCK / CATSKILLS GETAWAY... Cozy, private & light-filled Woodstock cottage designed for comfort, relaxation & rejuvenation. Perfect for romantic weekends, country getaways, or solo retreats. Private deck with mountain views. 5-minute drive to downtown...
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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • 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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    Stunning Vacation Country & Ski House1 / 23
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • 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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    Woodstock, Catskill Region 12463
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    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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    Spectacular, Luxurious Home on 12 acres w/ Mountain Views, Privacy, Space1 / 24
    (16)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Grill
    • Patio
    • Internet Access
    • Balcony
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Olive Oasis Luxury with Hot Tub, Woodstock Area1 / 26
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed June 25, 2014
    Me and my husband took our parents and our 5 month puppy for the very first family getaway. Dina (the owner) made it super easy for us. All the appliances are easily accessible...
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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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    Woodstock, Catskill Region 12481
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Secluded Cabin In The Heart of Woodstock1 / 18
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2016
    Secluded but not remote, modern but cozy, eat-off-the-floors clean with a well-stocked kitchen and a wrap-around deck with gorgeous views of rustling trees, Sage is a magical...
    Reviewed September 29, 2015
    My boyfriend and I stayed here for a long weekend. It's small, but perfect for a couple. Everything was clean had worked properly. The hot tub was great. It's a little closer to...
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    About this property
    Come for the perfect romantic getaway. Newly renovated, one bedroom, luxury cabin, in the heart of Woodstock. Secluded and private on 6 acres of forest and open land. Soak in the hot tub and watch deer meander, wild turkey and woodpeckers. Large deck to BBQ and entertain on. Stay connected with...
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    Woodstock, Catskill Region 12498
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 4
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    NEW! Rock City Writer's Studio: Bucolic Setting,1 / 13
    (20)Excellent
    Studio, 2 Bathrooms, Sleeps 2 Quick View
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    • Grill
    • Sauna
    • Internet Access
    • Central Heating
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Woodstock, Catskill Region 12498
    Condo/Apartment - 2 Bathrooms, Sleeps 2
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    Secluded, Luxury Home with Hot Tub1 / 19
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Parking
    • Wi-Fi
    • Grill
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed May 23, 2015
    Great communication with owner. House was clean and the kitchen had everything that we needed to make our own meals. Hot tub was perfect. Would have appreciated a king bed
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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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    CHARMING WOODSTOCK COUNTRY HOME w. Pool, Fireplac1 / 21
    (17)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Marigold cabin by the stream -  heart of Woodstock1 / 27
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Porch
    • DVD Player
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We have stayed at many properties of Mirav's and they're all amazing but this one is especially perfect very close to Woodstock, 30 minutes away from hiking up in the Catskills...
    Reviewed August 29, 2016
    ...Out of fear the cabin won't be available next time we want to rent it!!First of all, I must say. I am a very discerning traveler who typically stays in 4/5* hotels. I...
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    About this property
    Located at the heart of woodstock (on Ricks Rd) this newly built cabin is a dream gateway. Spacious, with all modern amenities, free wi-fi, cable TV, Netflix enabled, Gas fireplace, whisper quiet AC, romantic outdoor hot tub, large covered deck with infrared BBQ grill. Great lounging chairs to...
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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    NEW, SWIMMING,9 AC, MT VIEW, 2 BR, SCREENED PORCH,FRENCH DOORS,GAS FIRE PLACE.1 / 24
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Parking
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Woodstock Historic Artist Estate - The Cottage House1 / 21
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
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    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Romantic Luxury Chalet1 / 23
    (19)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Woodstock Way Bohemian Waterfall Studio, Heart of1 / 24
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Woodstock, Catskill Region 12498
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Parking
    • Air Conditioning
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Walk To Woodstock, Streamside W/In Ground Pool1 / 24
    (4)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    Sweet Woodstock Country Home - Great Spot For Hiking, Skiing And Mountain Air1 / 23
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
    • Central Heating
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    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    WOODSTOCK Modern Farmhouse w.Traditional Style, F1 / 24
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
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    Woodstock, Catskill Region 12498
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Woodstock Country House on 40 Acres, dogs OK.  WINTER SKI SPECIAL JAN-APR!1 / 23
    (10)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Woodstock, Catskill Region 12498
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brand new renovation, gorgeous contemporary cotta1 / 24
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Woodstock, Catskill Region 12498
    Rental Home - 1 Bathroom, Sleeps 4
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    Woodstock Way Bohemian Waterfall Studio, Heart Of1 / 24
    (19)Excellent
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Woodstock, Catskill Region 12498
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Private Yard
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two bedroom family year round cabin, the original summer home of local Woodstock artist Joseph Garlock. Newly renovated and decorated with his original artwork. Very private location nestled at the foot of Overlook Mountain on six acres of wooded land with brook running by. Unique stone fireplace...
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    Location Information
    Woodstock, Catskill Region 12498
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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