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Pet Friendly Holiday Rentals in Woodstock

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    Travellers to Woodstock are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    25 Matching Rentals in WoodstockView all 44 rentals
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    New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home1 / 85
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Secluded, Luxury Home with Hot Tub1 / 64
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet Friendly Cabin Doh-Ray Up At 1450ft1 / 33
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Marigold cabin by the stream -  Heart of Woodstock with Hot Tub & Fireplace1 / 27
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    Cute little well designed cabin a couple of miles walk from the village of Woodstock. As the weather was unseasonably miserable when we stayed, we certainly enjoyed the hot tub...
    Reviewed 10 July 2017
    We had an amazing time. the place was clean, well designed. Everything we needed was there. The hot tub under the starts was a great treat. LOVED the covered deck, we were able...
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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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    12498, Woodstock, Catskill Region
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Charming Artist's Cottage1 / 18
    (83)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2019
    We enjoyed our stay at this cabin. It is very well kept and extremely clean upon arrival. The owners were very helpful and informative with suggestions and recommendations...
    Reviewed 6 February 2019
    Like other previous travellers, I was looking to take a break from loud city life. I stayed for a long weekend with my dog. The cottage is beautifully decorated and super cozy...
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    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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    12498, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Mid Century Ranch-Hot Tub-Minutes to Center ofTown1 / 36
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    What a great place to gather with friends and family for an extended weekend! The decor of Casa Real is so much fun and the spacious interior and property on which the Casa is...
    Reviewed 2 August 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...
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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- 'we...
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    12498, Woodstock, Catskill Region
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Romantic Country Barn By the Stream1 / 26
    (21)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Hot Tub
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 March 2019
    We loved everything about the barn, it was easy to find, had a great hot tub and roomy interior. We finally relaxed after a long week and we enjoyed the local wildlife across...
    Reviewed 5 March 2019
    The Romantic Country Barn was a fabulous place to stay. While you're right next door to the owner, you would never know it. The placement of the barn makes you feel like you're...
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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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    12457, Woodstock, Catskill Region
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock1 / 40
    (3)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Air Conditioning
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Woodstock (Glasco Tpyk & Ricks Rd.) this cabin is the perfect romantic getaway. With 6 acres of of forest and open land as your back yard. Newly renovated, 2 bedrooms 1 bath, with wood-burning fireplace, Soak in the private hot tub and watch deer meander, wild turkey...
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    12498, Woodstock, Catskill Region
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski1 / 23
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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 8 August 2018
    This is a very handsome house in a spectacular setting. The house itself, a mid-century contemporary.. Lots of wood and glass, and you'll appreciate all that glass because...
    Reviewed 17 December 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...
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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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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts1 / 85
    (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
    • 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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    Location Information
    12457, Woodstock, Catskill Region
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Teahouse Cottage1 / 13
    (1)Excellent
    50 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Garden
    • Parking
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2018
    Great place for 4th of July activities grill n chill hikes river wades Woodstock town close by for provisions
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    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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    12498, Woodstock, Catskill Region
    Holiday Rental House - 50 Bedrooms, 1 Bathroom, Sleeps 4
    Cozy & Serene Cottage in Woodstock1 / 13
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Patio
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 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 29 June 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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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Woodstock Retreat, Sauna, Steam Shower, Decks1 / 22
    (3)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 16 July 2019
    This home is beautiful! The beauty can be seen as you drive up the road to it. When first seeing it you get the feeling that it is going to be just what you are looking for...
    Reviewed 10 August 2018
    Lovely residence with all the amenities and creature comforts for a relaxing and quiet getaway. Lots of light and multiple decks! The swimming pond was further away than...
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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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    Location Information
    12495, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Chic Retreat in Bearsville 2 m to Woodstock, Saline Pool, Fireplace and Hot tub.1 / 54
    (14)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2018
    I cannot emphasize how glad I am that I found this place most of our honeymoon trip. It is truly magical. We did not want to leave and hope to go back as soon as possible. The...
    Reviewed 9 October 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...
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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's 5 mins to Woodstock Village Green. Heated, saltwater pool, outdoor (hotwater) shower, hot tub, fireplace. Renovated in a relaxed lodge style. Local Spa 5 mins away to relax your mind spirit and...
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    Location Information
    12409, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Skiing: Property Is In A Ski Resort
    • Patio
    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
    12498, Woodstock, Catskill Region
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Privacy & Luxury @  Heart of Woodstock w/ Hot Tub1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2017
    I came here to celebrate my 25th birthday with my boyfriend, brother, and sister-in-law..as soon as we stepped foot into the cabin we were speechless! The cabin is BEYOND...
    Reviewed 13 April 2015
    We stayed here for my boyfriend's 30th birthday and had a blast! The home looks the exact way it does in the photos. The owner was very helpful and gave great suggestions for...
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    About this property
    Perfect romantic getaway, totally private. Beautiful 1600 sq. ft modern house, newly constructed, 2 bedrooms/2 baths, tucked away in the woods on a 6 acres lot, at the heart of enchanted Woodstock, in the historic Byrdcliffe area. Enjoy your private hot tub, relax and watch the meandering deer....
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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your next New York getaway at this lovely 2-bed, 2-bath vacation rental house in Woodstock! This 1,800-square-foot home sleeps 6 and is suitable for events hosting up to 50 people. Situated 5 minutes north of this home is the heart of Woodstock - brimming with unique shops, cafes, &...
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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this beautiful restored barn built in the 1840s. Three bedrooms, large living room and a big kitchen for a small group. Enjoy beautiful natural views on the porch in the quiet evenings. Grill in the backyard next to the creek. Relax with hot drinks around the fireplace. Watch deer and wild...
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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Contemporary, Secluded Cabin In The Heart of Woodstock1 / 24
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    We had a wonderful time. Cabin was everything we hoped it would be and more. The hot tub was especially nice!
    Reviewed 10 July 2017
    We celebrated our 12 year anniversary at Sage, what a perfect choice!! the cabin was off-the-floor clean. the bed supper comfortable. The location is great, a minute drive to...
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    About this property
    Come for the perfect romantic getaway. Newly renovated, one bedroom, contemporary cabin, in the heart of Woodstock. Secluded and private on 6 acres of forest and open land. Soak in the hot tub while watching deer meander, wild turkey, woodpeckers and more. Large deck to BBQ and entertain on. Stay...
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    Location Information
    12498, Woodstock, Catskill Region
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Bearsville retreat begins at this 2-bedroom, 1-bathroom vacation rental cabin. The perfect home-base for a group of 3 guests, this adorable abode features all the comforts and amenities you'll need to settle in. Situated just a short drive from local markets and other attractions, there's...
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    Location Information
    12409, Bearsville, Woodstock
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
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    Location Information
    12409, Bearsville, Woodstock
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    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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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Housekeeping Included
    • Central Heating
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our cottage-like house in the forest is surrounded by an acre of gardens with places to sit and enjoy nature. House & gardens set within tranquil forest are 10-minute walk to beautiful village of Woodstock, with its restaurants, boutiques, wine bars, & music venues. The house offers skylights, bay...
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    Location Information
    12498, Woodstock, Catskill Region
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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