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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (301 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 SAR 639
SAR 1,317 total
includes taxes & fees
20 Oct - 21 Oct
Streamside Cottage Half Mile to Town of Woodstock
A wooden deck with a bench, surrounded by a forested area.

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (36 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
The price is SAR 473
SAR 744 total
includes taxes & fees
5 Oct - 6 Oct
West Wing - a unique private space w/patio
A modern kitchen with a central island, black cabinetry, and pendant lighting.

3. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (13 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 SAR 2,058
SAR 3,596 total
includes taxes & fees
5 Oct - 6 Oct
Woodstock Historic Artist Estate - The Museum House
Private kitchen

4. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (12 reviews)
"Oh, I gave this property excellent scores for all the questions but I am reminded now by the suggestions for what to write about about the fact that it listed an Ocean view, which is obviously a mistake. It’s nowhere near the ocean. There’s no ocean view. It is in the woods it’s secluded.I actually took a very little walk in the middle of the night in the dark using my cell phone flashlight and got kind of lost for a while, but managed to find my way back. That was quite an interesting...
United States
Michael H.
The price is SAR 428
SAR 757 total
includes taxes & fees
5 Oct - 6 Oct
Woods Cabin-Kingston/Woodstock, NY.
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

5. 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 SAR 383
SAR 1,077 total
includes taxes & fees
27 Oct - 28 Oct
Campfire Cottage: Fireplace, fire pit & no chores!
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

6. 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, (103 reviews)
"Wonderful stay. "
United States
Chris L.
The price is SAR 642
SAR 1,009 total
includes taxes & fees
20 Oct - 21 Oct
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

7. 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, (313 reviews)
"Excellent place"
United States
Yeudin
The price is SAR 698
SAR 917 total
includes taxes & fees
1 Nov - 2 Nov
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

8. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (315 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
The price is SAR 469
SAR 526 total
includes taxes & fees
6 Oct - 7 Oct
Starlite Motel
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

9. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is SAR 526
SAR 857 total
includes taxes & fees
6 Oct - 7 Oct
Jessie's Harvest House
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

10. 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 SAR 1,277
SAR 2,835 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Mid-Century Retreat with Spa Hot Tub
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

11. 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 SAR 285
SAR 955 total
includes taxes & fees
27 Oct - 28 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A single-story house with a porch, a chimney, and a well-maintained lawn.

12. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
The price is SAR 507
SAR 1,304 total
includes taxes & fees
2 Oct - 3 Oct
Country House offers 2 bedrooms and a den, lots of parking.
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

13. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
The price is SAR 353
SAR 650 total
includes taxes & fees
20 Oct - 21 Oct
Jessie's Harvest House Suite
A log cabin with a porch, a staircase, and a garage.

14. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (34 reviews)
"Loved how secluded it was ,the quietness the unit was exceptional clean & fresh , The grounds are expertly groomed with a ,firepit and a really nice hot tub will be back again as a 3 &4 bedroom unit is availiblealso"
United States
alain
The price is SAR 488
SAR 835 total
includes taxes & fees
4 Oct - 5 Oct
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A room with a wooden cabinet, a glass door leading to a closet, a blue patterned rug, and a wooden floor.

15. 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, (40 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 SAR 639
SAR 1,426 total
includes taxes & fees
20 Oct - 21 Oct
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
A wooden vanity with a mirror, two pendant lights, and a folded towel.

16. Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
Stone Ridge
9.4 out of 10, Exceptional, (30 reviews)
"Great location close to town. Cute and clean. Great little spot."
United States
Stephen
The price is SAR 375
SAR 674 total
includes taxes & fees
28 Oct - 29 Oct
Historic Hudson Valley Farmhouse Loft in Stone Ridge Hamlet
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

17. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is SAR 477
SAR 1,096 total
includes taxes & fees
6 Oct - 7 Oct
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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.

18. 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 SAR 491
SAR 1,071 total
includes taxes & fees
28 Oct - 29 Oct
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
A fireplace with a stone wall, a stack of firewood, and a bookshelf with books.

19. 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)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is SAR 460
SAR 1,134 total
includes taxes & fees
5 Oct - 6 Oct
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

20. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (37 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
The price is SAR 372
SAR 951 total
includes taxes & fees
7 Oct - 8 Oct
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
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

New Paltz Way Hotel

New Paltz Way Hotel

10/10 Excellent
"Brand new hotel across from Brass and Blossom in Water Street Market. The lobby is great, filled with games, books and records. Totally recommend!"
Jena 1-night trip
Posted 10 hours ago
New Paltz Way Hotel

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.