A river winding through a forested valley with autumn foliage.

Bearsville Vacation Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Bearsville vacation rentals

A natural setting with a stream, red chairs, and a forested area.

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (305 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 AED 559
AED 1,197 total
includes taxes & fees
10 Nov - 11 Nov
Streamside Cottage Half Mile to Town of Woodstock
A modern kitchen with a large island, a sink, and wooden stools.

2. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House
Woodstock
9.8 out of 10, Exceptional, (50 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
The price is AED 995
AED 2,188 total
includes taxes & fees
26 Oct - 27 Oct
Woodstock Historic Artist Estate - The Carriage House
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

3. A pleasant space in a pleasant neighborhood in a beautiful part of the country!

A pleasant space in a pleasant neighborhood in a beautiful part of the country!
Woodstock
10.0 out of 10, Exceptional, (9 reviews)
"Very nice property that met our needs perfectly. Clean and very well maintained rooms. Lots of wildlife, beautiful wooded area. Peter, the host, was lovely and helpful."
United States
Barbara A.
The price is AED 882
AED 1,788 total
includes taxes & fees
21 Oct - 22 Oct
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A modern kitchen with a central island, black cabinetry, and pendant lighting.

4. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
9.8 out of 10, Exceptional, (14 reviews)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
The price is AED 1,118
AED 2,343 total
includes taxes & fees
21 Oct - 22 Oct
Woodstock Historic Artist Estate - The Museum House
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

5. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (106 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is AED 576
AED 916 total
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

6. Cozy Mid-Century Retreat with Spa Hot Tub

Cozy Mid-Century Retreat with Spa Hot Tub
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"Great spot, close to town but removed enough to have total privacy. Thank you!"
United States
Alec M.
The price is AED 1,249
AED 2,773 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Mid-Century Retreat with Spa Hot Tub
A wooden deck with a bench, surrounded by a forested area.

7. West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (37 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
The price is AED 463
AED 740 total
includes taxes & fees
22 Oct - 23 Oct
West Wing - a unique private space w/patio
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

8. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (325 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is AED 558
AED 762 total
includes taxes & fees
18 Nov - 19 Nov
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Private kitchen

9. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (15 reviews)
"Thank you. What an experience!"
United States
Burc
The price is AED 419
AED 745 total
includes taxes & fees
22 Oct - 23 Oct
Woods Cabin-Kingston/Woodstock, NY.
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

10. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (320 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is AED 533
AED 597 total
includes taxes & fees
21 Oct - 22 Oct
Starlite Motel
A forested landscape with a wooden structure in the foreground.

11. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (34 reviews)
"Excellent stay"
United States
Laura S.
The price is AED 744
AED 1,355 total
includes taxes & fees
21 Oct - 22 Oct
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A hot tub in a natural setting with a tree and a body of water.

12. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (17 reviews)
"A nice relaxing spot."
United States
Darren F.
The price is AED 761
AED 1,481 total
includes taxes & fees
21 Oct - 22 Oct
Peaceful Riverfront Cottage with Private Hot tub
A two-story house with a covered porch and a small deck.

13. Modern Main Street Studio in Tannersville

Modern Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (8 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
The price is AED 444
AED 856 total
includes taxes & fees
21 Oct - 22 Oct
Modern Main Street Studio in Tannersville
An outdoor deck with a wooden deck, a grill, wicker chairs, and a red umbrella.

14. Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
9.2 out of 10, Wonderful, (10 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
The price is AED 988
AED 1,852 total
includes taxes & fees
21 Oct - 22 Oct
Umana's Cabin, cozy, comfy, 5+ acres of land
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

15. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AED 268
AED 921 total
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A room with a wooden cabinet, a glass door leading to a closet, a blue patterned rug, and a wooden floor.

16. 1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia
9.2 out of 10, Wonderful, (41 reviews)
"Such a spectacular and unique home- we loved the thoughtful touches placed throughout the house. Beds comfy, kitchen had everything you could need plus more. Easy walking access to great hiking! The front porch is a perfect place to have morning coffee and watch the rabbits!"
United States
joan b.
The price is AED 625
AED 1,403 total
includes taxes & fees
26 Oct - 27 Oct
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
A wooden cabin with a deck and stairs leading to a pool area.

17. The Bend: Meadow Suite • Pool • Sauna • Fire Pits

The Bend: Meadow Suite • Pool • Sauna • Fire Pits
Phoenicia
The price is AED 1,093
AED 1,973 total
includes taxes & fees
21 Oct - 22 Oct
The Bend: Meadow Suite • Pool • Sauna • Fire Pits
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

18. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is AED 253
AED 901 total
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A residential area with a main road, houses, and a lake.

19. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is AED 433
AED 739 total
includes taxes & fees
25 Oct - 26 Oct
Jessie's Harvest House
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

20. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 reviews)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
The price is AED 432
AED 994 total
includes taxes & fees
21 Oct - 22 Oct
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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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Top Bearsville Hotel Reviews

Kingston Regency Inn

Kingston Regency Inn

8/10 Good
"Need twice as many towels because they are thin and not so big. The gym was a disappointment. The equipment needs to be serviced for example one treadmill needs to have the display fixed. Also many of the weights are missing and there were no towels. The breakfast during the week is not good. Weekend was better. But overall the room was quiet and comfortable and that is what matters the most."
Diane 3-night trip
Posted 6 hours ago
Kingston Regency Inn

Frequently asked questions

Can I find vacation rentals in Bearsville?

Yes, we give you a choice of vacation rentals close to well known points of interest in Bearsville, or you can go with a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals in Bearsville?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home near Bearsville is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Bearsville?

Choose from 17 Expedia vacation rentals in Bearsville for a memorable vacation.

What can I see and do in Bearsville?

Explore the area and family-friendly sights such as Hudson River Maritime Museum, or get out into nature at a spot like Overlook Mountain Trailhead. In the larger area, you’ll find Bearsville Theater and Ashokan Rail Trail- Woodstock Dike Trailhead.

What are vacation rentals like in Bearsville?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Bearsville. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.