Woodstock Rentals
From $259 per night (USD)VRBO
Cedar Cottage with hot tub
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This cottage was featured in the Escape Section of the New York Times. The house is in a great location, six minutes by ...
From $259 per night (USD)VRBO
From $569 per night (USD)VRBO
Cozy 2 bedroom cottage & heated pool mountain views bbq swim 🏊♂️ hike
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Stay in a lovely pristine 2 bedroom modern country cottage with mountain views on 10 acres, just 3 minutes from town. H ...
From $569 per night (USD)VRBO
From $600 per night (USD)VRBO
High Above It All In Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our beautiful and welcoming home, perched high above the Ashokan Reservoir, is spacious, well appointed, sun filled, and ...
From $600 per night (USD)VRBO
From $595 per night (USD)VRBO
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our pool is now closed until mid-May, 2024. (NOTE: Unlike other Hosts, we DO NOT charge you an extra fee to heat our poo ...
From $595 per night (USD)VRBO
From $567 per night (USD)VRBO
Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Bearsville Retreat is a secluded bucolic compound nestled in the trees of Bearsville, a quarter mile from the gourme ...
From $567 per night (USD)VRBO
From $385 per night (USD)VRBO
Woodstock Mid-Century Gem in the Woods - Secluded Getaway Close to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
You will have total privacy and safety on four wooded acres, 1.1 miles from the Woodstock village green. Enjoy the eclec ...
From $385 per night (USD)VRBO
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Byrdcliffe Retreat, Woodstock, NY
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Located in historic Byrdcliffe, surrounded by forever wild land, attached studio cabin features rustic charm, a single b ...
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From $211 per night (USD)VRBO
Woodstock Cooper Lake Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Woodstock country cottage walking distance to Cooper Lake. Minutes to center of Woodstock and the Bearsville Theater. Su ...
From $211 per night (USD)VRBO
From $149 per night (USD)VRBO
Stunning Woodstock NY Chalet with panoramic Catskill Mountains Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mt. Guardian Guest House is a serene designer space in the Woodstock region of the New York Hudson Valley. We host as we ...
From $149 per night (USD)VRBO
From $192 per night (USD)VRBO
Tree Top HideAway - Rural Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Open-plan apartment with high ceiling, wood stove, bedroom, office with sofa bed, (it MUST be specifically requested if ...
From $192 per night (USD)VRBO
From $507 per night (USD)VRBO
NEW! 5 MINUTES TO TOWN\/ LEVON'S~EXCEPTIONAL~ ROMANTIC~14 ACRES~DOGS WELCOME
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Our Woodstock getaway home is nestled in the woods next to a stream on 13+ acres yet only 5 minutes to town. Enter throu ...
From $507 per night (USD)VRBO
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Wydeclove Artist Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a secluded retreat in an original Birdcliff-style artist cabin: completely updated with air conditioning, Wifi and ...
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From $893 per night (USD)VRBO
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located just a three-minute drive or a leisurely stroll to the center of Woodstock, this stunning five bedroom contempor ...
From $893 per night (USD)VRBO
From $1171 per night (USD)VRBO
Gorgeous Designers Home With Award Winning Gardens And A Fabulous Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
. This home and acres of gardens surrounding it, are our life's work - and have been featured in news papers and magazi ...
From $1171 per night (USD)VRBO
From $250 per night (USD)VRBO
In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Woodstock (Glasco Tpyk & Ricks Rd.) this cabin is the perfect romantic getaway. With forest and ...
From $250 per night (USD)VRBO
From $176 per night (USD)VRBO
Relaxing Catskills Cottage in Nature
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
⭐️⭐️⭐️⭐️⭐️ About this space: Beautiful spacious Cottage in historic Woodstock surrounded by nature. The Cottage is nea ...
From $176 per night (USD)VRBO
From $439 per night (USD)VRBO
Mid-Century Artist Cottage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience fall and winter in our comfortable mid-century home located in this hamlet of Woodstock. Close to town for co ...
From $439 per night (USD)VRBO
From $850 per night (USD)VRBO
Private Mid Century Retreat with Pool & Mountain Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
OUR MAGICAL BEARSVILLY PROPERTY OVERVIEW *Newly Listed* Sitting on 3 acres, including a fern-lined stream, pine forest, ...
From $850 per night (USD)VRBO
From $252 per night (USD)VRBO
Pet Friendly Cabin Doh-Ray up @ 1500 ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
3 -30 day minimum depending on season. Discount with 7 days. + Surrounded by the forests of Mt. Guardian at an altitude ...
From $252 per night (USD)VRBO
From $1616 per night (USD)VRBO
Modern Glass House, Minutes to Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to one of the most beautiful homes in upstate New York. Perched on the edge of a ravine with huge windows, mult ...
From $1616 per night (USD)VRBO
From $773 per night (USD)VRBO
Heated pool, outdoor deck, fire pit, basketball court, fireplaces, central air.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The pool is open from May 22, 2024 until October 7, 2024. We supply 50 gallons of gas for the pool heater weekly; guests ...
From $773 per night (USD)VRBO
From $763 per night (USD)VRBO
Gorgeous Tuscan inspired private oasis, Heated pool, 5 min to Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Woodstock Villa is a stunningly elegant secret gem nestled in the heart of the Catskills Mountains. Located on one o ...
From $763 per night (USD)VRBO
From $590 per night (USD)VRBO
Woodstock walk to town, entire home and property to yourself, mountain views.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Broadview Retreat House is located in Woodstock NY. The house is a 10 minute walk to Tinker Street, the center of town. ...
From $590 per night (USD)VRBO
From $500 per night (USD)VRBO
Mid-Century Gem with Heated Pool 1 Mile from Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern Gem in Woodstock. 1960 stone and glass mint condition 3 bedroom immaculate home. Private yet less than a mile fro ...
From $500 per night (USD)VRBO
From $463 per night (USD)VRBO
Cottonwood-A Luxury Woodstock Home Located Between Woodstock + Saugerties
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Cottonwood! An upscale 3 bedroom, private office/convertible bedroom, 2 bath, in a lovely, newly renovated sp ...
From $463 per night (USD)VRBO
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Woodstock mountainside retreat, nicest view in the Catskills!! RELAX!!!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is our custom built timber-frame post and beam home, built in 2006. Home has a certified short term rental permit f ...
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From $259 per night (USD)VRBO
Red Maple Studio & Spa: Steam, Stream & Dream at Sawkill in Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 2.5 miles from the heart of Woodstock and 10 minutes to uptown Kingston! Enjoy our custom-designed 400 sq ft studi ...
From $259 per night (USD)VRBO
From $400 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 $400 per night (USD)Expedia
From $450 per night (USD)VRBO
Iconic Byrdcliffe estate property with in-ground pool on 10 acres.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Take it easy at this tranquil getaway in the Catskills. This historic Byrdcliffe property was built in 1898 by an artisa ...
From $450 per night (USD)VRBO
From $240 per night (USD)Expedia
CAPE ESCAPE IN THE MOUNTAINS
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our house is located on 1.5 acres of land, with a sunny deck just off the kitchen that features outdoor dining, and a ga ...
From $240 per night (USD)Expedia
From $499 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 $499 per night (USD)VRBO
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 $235 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 $235 per night (USD)VRBO
From $275 per night (USD)VRBO
Amazing Views at Skyloft, Affordable, Totally Pvt.
- 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 $275 per night (USD)VRBO
From $395 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 $395 per night (USD)VRBO
From $145 per night (USD)VRBO
Country Cabin in Woodstock, NY- Cozy and Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $145 per night (USD)VRBO
From $190 per night (USD)VRBO
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 $190 per night (USD)VRBO
From $610 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 $610 per night (USD)VRBO
From $770 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 $770 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $299 per night (USD)VRBO
Woodstock Getaway w\/ Hot Tub ~ 2 Mi to Dtwn!
- Bedrooms:
- 3
- 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 $299 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 ...
Click For PricingExpedia
From $296 per night (USD)VRBO
Charming Getaway in Woodstock\/ w hot tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Forget your worries and spend some quality time with friends and family on a spacious and serene property. Enjoy your ti ...
From $296 per night (USD)VRBO
From $341 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 $341 per night (USD)Expedia
From $526 per night (USD)VRBO
Wooded Mid-Century Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience your own luxury secluded Mid-Century forest home yet only be five minutes from historically fabulous Woodstoc ...
From $526 per night (USD)VRBO
From $257 per night (USD)VRBO
Woodstock retreat w\/hot tub, 5 min from Town
- 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 $257 per night (USD)VRBO
From $789 per night (USD)VRBO
The 212 Escape
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Amazing amenities include: - 5 person sauna (so relaxing you won’t want to leave) - Cal spa hot tub (available all year ...
From $789 per night (USD)VRBO
From $400 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 $400 per night (USD)Expedia
From $209 per night (USD)VRBO
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 ...
From $209 per night (USD)VRBO
From $374 per night (USD)Expedia
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 $374 per night (USD)Expedia
From $250 per night (USD)VRBO
Cosy Catskills Cabin, minutes to Woodstock Village.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy yet stylish, packed full of original details, this unique 2-bedroom stone cabin offers comfort and charm in equal m ...
From $250 per night (USD)VRBO
From $185 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 $185 per night (USD)VRBO
From $360 per night (USD)VRBO
Brand new magical cottage in the Woodstock woods with w\/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 $360 per night (USD)VRBO
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Seasonal rental one mile to Woodstock, near skiing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Take it easy at this unique and tranquil getaway. If relaxation is what you are looking for then this is your place. Min ...
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From $198 per night (USD)VRBO
Frolic & Focus in this Bright Stylish Woodstock Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This bright stylish guest house is 5 minutes from fresh croissants in downtown Woodstock and 10 minutes from the gloriou ...
From $198 per night (USD)VRBO
From $135 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 $135 per night (USD)VRBO
From $525 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 $525 per night (USD)VRBO