Bearsville Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveler
$267 nightly
The price is $299
Nov 11 - Nov 12
Total with taxes and fees
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, (51 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
$430 nightly
The price is $481
Nov 11 - Nov 12
Total with taxes and fees
Woodstock Historic Artist Estate - The Carriage House
A wooden deck with a bench, surrounded by a forested area.

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (40 reviews)
"Clean and beautifully decorated room. Very comfortable, excellent bed and linens. Friendly and knowledgeable staff. An "out of the way " place and that's its charm, yet close enough - short car rides- to restaurants and other attractions. We'd gladly return!"
United States
Ronald
$186 nightly
The price is $208
Nov 11 - Nov 12
Total with taxes and fees
West Wing - a unique private space w/patio
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

4. 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.
$448 nightly
The price is $496
Nov 11 - Nov 12
Total with taxes and fees
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
Private kitchen

5. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (17 reviews)
"We loved the little cabin in the woods!"
United States
Patti G.
$182 nightly
The price is $203
Nov 11 - Nov 12
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

6. 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, (341 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
$192 nightly
The price is $207
Dec 10 - Dec 11
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, black cabinetry, and pendant lighting.

7. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
9.8 out of 10, Exceptional, (16 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.
$620 nightly
The price is $694
Nov 11 - Nov 12
Total with taxes and fees
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.

8. 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, (112 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
$229 nightly
The price is $256
Nov 16 - Nov 17
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

9. Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
10.0 out of 10, Exceptional, (21 reviews)
"This was a beautiful little spot and had everything! We loved our 3 night stay."
United States
Holly
$762 nightly
The price is $766
Nov 21 - Nov 22
Total with taxes and fees
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
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.
$641 nightly
The price is $718
Nov 22 - Nov 23
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

11. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
$145 nightly
The price is $162
Nov 11 - Nov 12
Total with taxes and fees
Starlite Motel
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

12. 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.
$216 nightly
The price is $242
Nov 17 - Nov 18
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

13. 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.
$181 nightly
The price is $191
Nov 15 - Nov 16
Total with taxes and fees
Jessie's Harvest House
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

14. 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, (7 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.
$207 nightly
The price is $232
Nov 16 - Nov 17
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

15. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
$254 nightly
The price is $284
Nov 18 - Nov 19
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
A house with a porch, a small balcony, and a garden with various plants and flowers.

16. Modern Main Street Studio in Tannersville

Modern Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (10 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
$201 nightly
The price is $217
Nov 11 - Nov 12
Total with taxes and fees
Modern Main Street Studio in Tannersville
A living room with a stone fireplace, leather sofa, and a mounted TV displaying 'NETFLIX'.

17. Hunter Mountain`s Only True Ski In Ski Out Condo

Hunter Mountain`s Only True Ski In Ski Out Condo
Hunter Highlands
10.0 out of 10, Exceptional, (23 reviews)
"You will definitely return this place is cozy, clean and convenient! "
United States
Elizabeth C.
$219 nightly
The price is $238
Nov 11 - Nov 12
Total with taxes and fees
Hunter Mountain`s Only True Ski In Ski Out Condo
A forested landscape with a wooden structure in the foreground.

18. 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.
$327 nightly
The price is $353
Nov 11 - Nov 12
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

19. 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, (39 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$224 nightly
The price is $251
Nov 16 - Nov 17
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

20. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
$226 nightly
The price is $253
Nov 11 - Nov 12
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
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

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

One of the coolest and most accommodating places I have ever stayed. If you are coming to Woodstock are even thinking about it this is the place for you. All the rooms are unique, they are super clean and look exactly like they do online. The owner is amazing and she will point you in the right direction for whatever you are looking to do in town. Seriously cannot recommend enough and can’t wait to come back.
United States
Noah
Reviewed January 16, 2023
Twin Gables of Woodstock

Find out more about Bearsville

Everything you need to know about Bearsville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bearsville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bearsville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bearsville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bearsville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bearsville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bearsville rentals

At Expedia, we put the best Bearsville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bearsville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bearsville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bearsville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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