Woodstock Rentals
From $362 per night (USD)VRBO
The Mod Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Discover a cute Catskills hideaway: a warm, cozy and stylish vacation home perfectly located by the dow ...
From $362 per night (USD)VRBO
From $458 per night (USD)Expedia
Woodstock Artist's Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Relax, create, and enjoy the Woodstock Artist's Retreat. 6 serene acres hugged by magical Overlook Mountain, Lewis ...
From $458 per night (USD)Expedia
From $135 per night (USD)VRBO
A Wonderful House. High on a hill overlooking the mountains and valleys.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
We want to rent only for the season, from November 15th until March 31st. We have a beautiful, light-filled modern hous ...
From $135 per night (USD)VRBO
From $219 per night (USD)VRBO
The CubHouse
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WOODSTOCK/BEARSVILLE Escape to a little healing magic in this 1909 built cottage. Originally owned by a medicine woman i ...
From $219 per night (USD)VRBO
From $270 per night (USD)VRBO
Unequalled Views of Reservoir & Mtns, Affordable, Totally Private
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
SKYLOFT, your own private piece of the world. Quiet, away from everything, yet not isolated.. SKYLOFT is a 1000-sq-ft ap ...
From $270 per night (USD)VRBO
From $377 per night (USD)VRBO
Cozy vacation home in the Catskills
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover a cute Catskills hideaway: a warm, cozy and stylish vacation home perfectly located by the downtown area and so ...
From $377 per night (USD)VRBO
From $354 per night (USD)VRBO
NEW! Woodstock-Private-Exquisite-Modern A-Frame-Minimum Stays are Monthly!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Style meets convenience for a relaxing and peaceful stay. Plan your MONTH-LONG visit to the Hudson Valley and use Wood ...
From $354 per night (USD)VRBO
From $211 per night (USD)VRBO
Romantic Luxury Chalet
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dear Traveler, Look no further. This quiet, private and very romantic chalet exudes character, luxury and charm. P ...
From $211 per night (USD)VRBO
From $148 per night (USD)VRBO
Country Cabin in Woodstock, NY- Cozy and Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Two night minimum stay. Please do not request a one night stay as that is not an option. Country Cottage Retreat in be ...
From $148 per night (USD)VRBO
From $461 per night (USD)Expedia
Quaint Woodstock Escape - 2 Mi to Tinker St!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Highlighted by its spacious grounds and close proximity to restaurants, entertainment, and shopping, this secluded Woods ...
From $461 per night (USD)Expedia
From $490 per night (USD)VRBO
Fall Foliage Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Recently featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCent ...
From $490 per night (USD)VRBO
From $470 per night (USD)VRBO
Mountainside home, with pool , deck & 3mins to Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This charming home sits on 5 acres and walking distance to the Village of Woodstock. It is stylishly decorated & include ...
From $470 per night (USD)VRBO
From $777 per night (USD)VRBO
Exceptional Property, Saline Pool, Waterfall, Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This lovely home is available August through Labor Day. Beautifully updated farmhouse featured in Good Housekeeping & Co ...
From $777 per night (USD)VRBO
From $195 per night (USD)Expedia
Woodstock Waterfall Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Waterfall Cottage is on 2 1/2 privet acers and 2 1/2 miles to the center of the town of Woodstock. The Sawkill and ...
From $195 per night (USD)Expedia
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NEW! Bright and Cheerful Historic Cottage in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Step into a piece of history! Built in 1930 by Bolton Brown, an original founder of the Woodstock Artist Colony, this Ar ...
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From $477 per night (USD)Expedia
RETREAT TO SPENCER COTTAGE Relax w. Friends Family
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hidden away on top of Ohayo Mtn., Spencer Cottage is casual, comfortable, and private. 3 cozy bedrooms & 2 full baths ac ...
From $477 per night (USD)Expedia
From $492 per night (USD)VRBO
Family Oasis - Minutes from Hiking & Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Town of Woodstock Special Use (aka STR) Permit #23-0683 Featured in Hudson Valley Style Magazine, this fully renovated ...
From $492 per night (USD)VRBO
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NEW! The Joyful Cabin - Modern Upstate Cabin Vibe
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our joyful cabin is nestled on 6 wooded acres - this is the perfect place to rest and recharge. Soak in the sights in th ...
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From $385 per night (USD)VRBO
Woodstock Getaway w\/ Hot Tub ~ 2 Mi to Dtwn!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 8
Visit renowned music venues, chase waterfalls, and enjoy the natural beauty of the Catskills when you stay at this all-s ...
From $385 per night (USD)VRBO
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Away Upstate, a cozy retreat w\/ Firepit and Wood Stove
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space: The Away Upstate retreat is nestled in the breathtaking Catskills and is your perfect home away from h ...
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From $308 per night (USD)VRBO
Saugerties retreat, hot tub, 10 min from Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Peaceful, cozy country house, prime location, private deck with hot tub and proximity to the towns of Woodstock and Saug ...
From $308 per night (USD)VRBO
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Chestnut Hill Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ecently renovated artist studio located in Woodstock, the Country's Most Famous Small Town in America! Everything is bra ...
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From $190 per night (USD)VRBO
Private Woodstock cottage. Don't forget your dog!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy the music, art, shopping and restaurants of Woodstock in the winter holiday season! Hike the many trails, explor ...
From $190 per night (USD)VRBO
From $192 per night (USD)VRBO
Imagine The Woodstock House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Woodstock House is distinctive and gracious. The Woodstock house is ideally located within walking distance to the ...
From $192 per night (USD)VRBO
From $311 per night (USD)VRBO
Magical cottage in the Woodstock woods with with heated pool and firepit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Magical cottage in the woods just outside of Woodstock. Relaxed and charming, meticulously appointed and newly renovated ...
From $311 per night (USD)VRBO
From $141 per night (USD)VRBO
Woodstock Country Guest Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Warm and inviting guest suite with private driveway and entrance in an extremely quiet neighborhood, around the corner f ...
From $141 per night (USD)VRBO
From $379 per night (USD)VRBO
Gorgeous Villa w\/ Mountain Views, pool, hot tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please note this house has been rented under a previous owner for years with 5 star reviews, I also managed the house fo ...
From $379 per night (USD)VRBO