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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Bearsville cottages

A wooden cabin surrounded by lush greenery and trees.

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (308 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is £225
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

2. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (21 reviews)
"Artsy, comfortable and cozy cottage in a country setting. Love the deck for grilling! This was our second time here and we hope to be back again!"
United States
Laura G.
The price is £225
includes taxes & fees
11 Nov - 12 Nov
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

3. Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken
10.0 out of 10, Exceptional, (2 reviews)
"It was a charming and cozy cabin nested in the woods. Perfect size for two people."
United States
afsoon p.
The price is £148
includes taxes & fees
18 Nov - 19 Nov
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
A kitchen with white cabinetry, granite countertops, and a window with blinds.

4. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is £184
includes taxes & fees
16 Nov - 17 Nov
Charming loft cottage in tranquil Germantown with WiFi, AC
A single-story house with a dark exterior, a chimney, and a small window.

5. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is £361
includes taxes & fees
5 Nov - 6 Nov
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

6. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
The price is £148
includes taxes & fees
12 Nov - 13 Nov
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

7. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (29 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is £255
includes taxes & fees
10 Nov - 11 Nov
Charming Cottage in the Heart of Catskill & Pet Friendly
A wooden deck with a white railing, surrounded by lush green trees.

8. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (25 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is £392
includes taxes & fees
5 Nov - 6 Nov
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A snow-covered ground with footprints leading to a house with a solar panel roof.

9. Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
The price is £309
includes taxes & fees
5 Nov - 6 Nov
Tiny House on Walnut Grove
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Bearsville

Venture to Bearsville Theater and Overlook Mountain Trailhead—just two of the sights around Bearsville.

See all hotels in Bearsville
A river winding through a forested valley with autumn foliage.

Top reviews in Bearsville

A white house with a green door, black trim, and a porch with a lantern.
Twin Gables of Woodstock

Twin Gables of Woodstock

Twin Gables of Woodstock
Woodstock

10/10 Excellent

Beautifully decorated in a homely style and in keeping with the Woodstock vibe. Excellent location for all the excellent bars and restaurants and shops. We also appreciated a TV free property!
United Kingdom
Kevin
Reviewed September 20, 2025
Twin Gables of Woodstock

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