Search Bearsville Cottage Rentals from CA $143

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveller
The price is CA $202
CA $422 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $173
CA $442 total
includes taxes & fees
Nov 16 - Nov 17
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A kitchen with white cabinetry, granite countertops, and a window with blinds.

3. 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 CA $171
CA $331 total
includes taxes & fees
Dec 1 - Dec 2
Charming loft cottage in tranquil Germantown with WiFi, AC
A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

4. 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 CA $143
CA $260 total
includes taxes & fees
Nov 30 - Dec 1
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
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 CA $339
CA $682 total
includes taxes & fees
Nov 12 - Nov 13
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)
"A cozy little cabin. A great place to enjoy in itself and a relaxing place to come back to after a day out. Stayed two nights and went hiking, great location for the mountains. Host was very responsive."
United States
Devon Q.
The price is CA $188
CA $319 total
includes taxes & fees
Dec 1 - Dec 2
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, (31 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 CA $282
CA $511 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $507
CA $753 total
includes taxes & fees
Nov 15 - Nov 16
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
An outdoor patio area with a pergola, seating, and a barbecue grill.

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 CA $286
CA $579 total
includes taxes & fees
Nov 12 - Nov 13
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

Head 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 living room with a fireplace, green sofa, and a leopard print armchair.
Twin Gables of Woodstock

Twin Gables of Woodstock

Twin Gables of Woodstock
Woodstock

10/10 Excellent

Cute property!
Canada
Paola
Reviewed July 14, 2026
Twin Gables of Woodstock

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