Yankeetown Pond Unit Rentals
From $274 per night (USD)VRBO
Mountainside Japanese Teahouse with heated salt water pool and tennis court
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come and stay at the Hudson Valley's only Japanese Teahouse, our hidden gem sits on the south facing side of a mountain ...
From $274 per night (USD)VRBO
From $285 per night (USD)Expedia
WOODSTOCK CHARMER: HIKING, NATURE, ELEPHANT ART SANCTUARY
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Close to beautiful hiking and lakes. Cozy artistic house on mountain foothills in scenic Bearsville, 10 mins from Woodst ...
From $285 per night (USD)Expedia
From $606 per night (USD)VRBO
Family-Friendly Retreat Close to Town w\/ Heated Pool & Hot Tub on 3 Acres
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Experience Woodstock, NY and the Catskill Mountains while staying at our lovely four-bedroom home. Located on nearly thr ...
From $606 per night (USD)VRBO
From $138 per night (USD)Expedia
Updated\/Pet-Friendly Cabin By Hikes and Woodstock!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Your Bearsville retreat begins at this 2-bedroom, 1-bathroom vacation rental cabin. The perfect home-base for a group of ...
From $138 per night (USD)Expedia
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LIFE ABOVE 1200’
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
This home is a very special place; top of the mountain, abundant wildlife, secluded, southern exposure, and super cozy c ...
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From $448 per night (USD)Expedia
Classic Catskills Estate, Amazing Location!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to Lachland! (We have new central A/C!) This 5 bedroom home has been a beloved family vacation home for 4 genera ...
From $448 per night (USD)Expedia
From $312 per night (USD)VRBO
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location is everything! Just a couple of miles from Woodstock village on a quiet dead end road. Ashokan Reservoir views ...
From $312 per night (USD)VRBO
From $280 per night (USD)Expedia
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summer at the Red Cottage! Relax by the hand-built stone fireplace, watch the birds and wildlife from outside on the pa ...
From $280 per night (USD)Expedia
From $238 per night (USD)VRBO
Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Treat yourself to a romantic getaway or family retreat in your own private log cabin on Ohayo Mountain, just 1.5 miles f ...
From $238 per night (USD)VRBO
From $695 per night (USD)VRBO
Classic 12 acre Woodstock Artists Estate w\/ shared saline pool and tennis court
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
The Peacock House is perched atop a private road on a sprawling 12-acre south facing mountain side estate, super seclude ...
From $695 per night (USD)VRBO
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 $588 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 $588 per night (USD)VRBO
From $595 per night (USD)VRBO
Modern Farmhouse Getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Shula Getaway sits on three acres of serene nature and rolling stone walls. Take full advantage of this 1,800 sq ft ...
From $595 per night (USD)VRBO
From $383 per night (USD)VRBO
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 ...
From $383 per night (USD)VRBO
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Cricket Ridge Mountain View Retreat
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Cricket Ridge, a private home on 57 acres with hillside walks, a stream and waterfall. This 4-bedroom, 3.5-ba ...
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From $219 per night (USD)VRBO
Dancing Angel Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cute and cozy with great views of the Ashokan Reservoir A great view from the patio with private entrance to the house. ...
From $219 per night (USD)VRBO
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 $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 $398 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 $398 per night (USD)VRBO
From $600 per night (USD)VRBO
Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
The cabin is cozy and rustic looking but with modern comforts. Featuring a large stone fireplace and expansive deck, gre ...
From $600 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 $193 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 $193 per night (USD)VRBO
From $671 per night (USD)VRBO
Bearsville Barn: Featured in Vogue - Renovated Barn w\/ 30 ft Ceilings and Historic Wood Beams
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Bearsville Barn is a beautifully restored 1889 gem—featured in Vogue and “Woodstock Handmade Houses—located just 8 m ...
From $671 per night (USD)VRBO
From $500 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 $500 per night (USD)VRBO
From $70 per night (USD)VRBO
Woodstock Cabin in the Woods
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Charming A-frame cabin in lovely private wooded setting. This stone and wood constructed cabin features a gorgeous work ...
From $70 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 $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 $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 $159 per night (USD)VRBO
Mid-Century Modern House Convenient to All that Woodstock has to Offer.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Marko Grove is a Mid-Century Modern Raised Ranch house on a large lot in Woodstock’s well-known Bearsville Flats neighbo ...
From $159 per night (USD)VRBO
From $254 per night (USD)Expedia
The Chapel at Upland, with heated salt water pool and new tennis\/bball court
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Indulge in the serenity of private and secluded country house, once a monk's sanctuary now a blend of history and luxury ...
From $254 per night (USD)Expedia
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Woodstock Grandeur Sleeps4-6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Only 5 minutes to famous Woodstock you will find our quiet, bucolic country setting with woodland views and hiking trail ...
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From $479 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 $479 per night (USD)VRBO
From $352 per night (USD)VRBO
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Our well-equipped cabin sits at the end of a dead-end road on three secluded acres including rolling lawn, woodlands, an ...
From $352 per night (USD)VRBO
From $245 per night (USD)VRBO
Hummingbird Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our beautiful and welcoming home, perched high above the Ashokan Reservoir, is spacious, well appointed, and sun filled. ...
From $245 per night (USD)VRBO
From $650 per night (USD)VRBO
Cozy 4 bedroom, just renovated -with Christmas decor, close to 3 skiing Mt
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Relax with your family and friends at this peaceful place to stay. Enjoy our favorable location that is close to multipl ...
From $650 per night (USD)VRBO