Woodstock Rentals
From $406 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 $406 per night (USD)VRBO
From $467 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 $467 per night (USD)Expedia
From $407 per night (USD)VRBO
Chic and eclectic retreat at Woodstock/Saugerties!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated old barn, circa 1810, with chic, modern and eclectic design, with landscaped lawn/garden. A wonder ...
From $407 per night (USD)VRBO
From $406 per night (USD)Expedia
NEW! ROMANTIC STORYBOOK COTTAGE Peaceful, Historic, Private, Charming
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located in Woodstock, this oh-so-charming home is a lovely choice for a couple or a couple of friends who want to get aw ...
From $406 per night (USD)Expedia
From $161 per night (USD)VRBO
Robin's Nest Studio in Woodstock with garden view of Ashokan
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to a cozy studio in a charming cottage atop Ohayo Mountain in the Catskills, where you can enjoy a stunning view ...
From $161 per night (USD)VRBO
From $422 per night (USD)Expedia
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 $422 per night (USD)Expedia
From $699 per night (USD)VRBO
Woodstock/Entire house with pool 1.5 miles to Village Green. Very private.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stylish and comfortable private home just 1.5 miles from Village Green with private lawn, woods. In ground pool with out ...
From $699 per night (USD)VRBO
From $331 per night (USD)Expedia
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 $331 per night (USD)Expedia
From $151 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 $151 per night (USD)VRBO
From $301 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 $301 per night (USD)VRBO
From $296 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 $296 per night (USD)VRBO
From $355 per night (USD)VRBO
Romantic Luxury Chalet with Private Pool
- 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 $355 per night (USD)VRBO
From $169 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 $169 per night (USD)VRBO
From $424 per night (USD)Expedia
Quaint Woodstock Escape - 2 Mi to Tinker St!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlighted by its spacious grounds and close proximity to restaurants, entertainment, and shopping, this secluded Woods ...
From $424 per night (USD)Expedia
From $637 per night (USD)VRBO
Fall Foliage Getaway!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Recently featured in Atomic Ranch & Country Home Magazines, the Maverick is a secluded luxuriously restored 1964 MidCent ...
From $637 per night (USD)VRBO
From $576 per night (USD)VRBO
Mountainside home, with pool , deck & 3mins to Woodstock
- Bedrooms:
- 2
- 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 $576 per night (USD)VRBO
From $870 per night (USD)VRBO
Exceptional Property, Saline Pool, Waterfall, Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This lovely home is available August through Labor Day. Beautifully updated farmhouse featured in Good Housekeeping & Co ...
From $870 per night (USD)VRBO
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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 ...
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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 $852 per night (USD)Expedia
Modern Farmhouse w/ Saltwater Pool, Game Room, Spa Baths - 5 Min to Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Woodstock Highlands, a beautifully renovated four-bedroom modern farmhouse nestled in the heart of the Hudson ...
From $852 per night (USD)Expedia
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NEW! The Joyful Cabin - Modern Upstate Cabin Vibe
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $401 per night (USD)Expedia
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Visit renowned music venues, chase waterfalls, and enjoy the natural beauty of the Catskills when you stay at this all-s ...
From $401 per night (USD)Expedia
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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 $454 per night (USD)VRBO
Saugerties-Woodstock retreat, hot tub, 5 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 $454 per night (USD)VRBO
From $381 per night (USD)VRBO
NEW! Bright and Cheerful Historic Cottage in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a piece of history! Built in 1930 by Bolton Brown, an original founder of the Woodstock Artist Colony, this Ar ...
From $381 per night (USD)VRBO
From $211 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 $211 per night (USD)VRBO
From $467 per night (USD)VRBO
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Property Overview: Relax and rejuvenate at this magical woodland cottage in Woodstock, New York. Tucked away in a tranq ...
From $467 per night (USD)VRBO
From $308 per night (USD)Expedia
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 $308 per night (USD)Expedia
From $154 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 $154 per night (USD)VRBO
From $496 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 $496 per night (USD)VRBO