Woodstock Rentals
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Savor Dreamy Treetop Views Under Whitewashed Beams
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Escape to your private, treetop hideout right in the village of Woodstock. Peaceful & private, this upper unit has an ea ...
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Explore Woodstock from an Exceptional Home
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Sit by the fire in a living room with hardwood floors, relaxed furnishings, and distressed wood accents. Have a cookout ...
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From $412 per night (USD)VRBO
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brook Cottage is ideally located on a shared and secluded property at the end of a private lane, yet it’s just a few blo ...
From $412 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 $284 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 $284 per night (USD)VRBO
From $459 per night (USD)Expedia
Bright, historic Woodstock home close to town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our historic Woodstock home is close to everything, but far enough away to be surrounded by trees, grass and peace & qui ...
From $459 per night (USD)Expedia
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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 $597 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 $597 per night (USD)Expedia
From $308 per night (USD)VRBO
A pleasant space in a pleasant neighborhood in a beautiful part of the country!\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a newly renovated apartment in and old studio. Close (1 mile) to the center of the village of Woodstock, NY. Wit ...
From $308 per night (USD)VRBO
From $153 per night (USD)Expedia
Adorable Red Cottage, walking distance to Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
We invite you to enjoy your time upstate in our Cozy Red Woodstock Cottage! This adorable, thoughtfully renovated 2 BR ...
From $153 per night (USD)Expedia
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 $915 per night (USD)VRBO
Luxury Woodstock Family Retreat with pool/hot tub
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
I will work with you on pricing! I have bee. A superhost on the other site for 7+ years. Yoy can find me on Insta at ren ...
From $915 per night (USD)VRBO
From $172 per night (USD)VRBO
Mid-Century Woodstock Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our mid-century Woodstock retreat! This one-level home features an open-concept layout that seamlessly blends ...
From $172 per night (USD)VRBO
From $398 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 $398 per night (USD)Expedia
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 $161 per night (USD)Expedia
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)Expedia
From $139 per night (USD)VRBO
Renovated home seconds from town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this newly renovated Woodstock Home (3BR/2.5 BA/1,595 sq ft). A dream getaway for those looking to fall in l ...
From $139 per night (USD)VRBO
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Charming 1-bedroom cottage in Woodstock with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Consider this cottage your home away from home while you visit Woodstock. This cozy retreat features 1 serene bedroom wi ...
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From $567 per night (USD)VRBO
Woodstock Secluded Close to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
About this space: Our beautiful family vacation home is a 1/2 mile to town and sits on a 3 acre parcel with a stunning M ...
From $567 per night (USD)VRBO
From $298 per night (USD)Expedia
PERFECT FAMILY RETREAT 4 Br, Heated Pool, Hot Tub, Minutes to Town, Pvt, Quiet
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home in the Bearsville hamlet of Woodstock, less than 10 minutes from Town, is the perfect family Retreat. There ar ...
From $298 per night (USD)Expedia
From $365 per night (USD)VRBO
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome To Your Colorful Modern Hideaway In The Heart Of Downtown Woodstock Part of a fully renovated property, this br ...
From $365 per night (USD)VRBO
From $202 per night (USD)VRBO
Serene Woodstock home with birdsong
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on nearly an acre of land, this beautiful home boasts and abundance of natural light that floods its spacious, h ...
From $202 per night (USD)VRBO
From $345 per night (USD)VRBO
Chronogram featured, Modern Mountain Family Home above Woodstock. Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Featured in Chronogram Magazine as a modern eco-friendly mountain home with geo thermal heating and cooling and solar po ...
From $345 per night (USD)VRBO
From $314 per night (USD)VRBO
Charming 3 Bedroom Cabin with Mountain Views in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect mountain retreat! Nestled on 15 private acres, this whimsical rustic cabin offers a magical esca ...
From $314 per night (USD)VRBO
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 $962 per night (USD)Expedia
Modern Farmhouse w/ Heated Pool & Creek Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to a beautifully restored farmhouse that blends timeless charm with modern comforts. Nestled in a peaceful, sceni ...
From $962 per night (USD)Expedia
From $393 per night (USD)Expedia
CLASSIC WOODSTOCK Minutes to Town, Heated Pool, Pond, Views, AC, WiFi, Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A classic Woodstock home on 4 private acres just minutes from the center of town. Heated pool in summer, views all year ...
From $393 per night (USD)Expedia
From $509 per night (USD)Expedia
Cozy Escape in Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Find complete country zen within walking distance of the village of Woodstock. This charming 3-bedroom has all ...
From $509 per night (USD)Expedia
From $370 per night (USD)VRBO
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Groovy Getaway in Woodstock – Vinyl Vibes & Retro Style! Step back in time to a groovier era in this colorful, music-lo ...
From $370 per night (USD)VRBO
From $2369 per night (USD)Expedia
NEW: Luxe Glass Contemporary w/ Pool + Guest House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights: If your ideal escape includes sleek, nature-immersive architecture, seamless single-level living, a shimmeri ...
From $2369 per night (USD)Expedia
From $548 per night (USD)VRBO
Secluded 3BR w/ Private Pool & Epic Views – 10 Mins to Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Craving space, quiet, and fresh mountain air? This 3-bedroom cliffside retreat is your ideal upstate escape—just two hou ...
From $548 per night (USD)VRBO