A river winding through a forested valley with autumn foliage.

Bearsville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (299 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.
$268 nightly
The price is $300
Sep 27 - Sep 28
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A modern kitchen with a central island, black cabinetry, and pendant lighting.

2. 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.
$547 nightly
The price is $612
Sep 28 - Sep 29
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

3. 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.
$639 nightly
The price is $716
Sep 28 - Sep 29
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

4. 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, (309 reviews)
"Excellent place"
United States
Yeudin
$201 nightly
The price is $217
Oct 26 - Oct 27
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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, (103 reviews)
"Wonderful stay. "
United States
Chris L.
$231 nightly
The price is $259
Sep 27 - Sep 28
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

6. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (314 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Sep 28 - Sep 29
Total with taxes and fees
Starlite Motel

7. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (1 review)
"The best "
United States
Miguel
$502 nightly
The price is $542
Sep 30 - Oct 1
Total with taxes and fees
Windham NY Escape
A wooden deck with a bench, surrounded by a forested area.

8. 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.
$176 nightly
The price is $197
Oct 5 - Oct 6
Total with taxes and fees
West Wing - a unique private space w/patio
A cabin with a wooden porch and a bed.

9. Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace

Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace
Tannersville
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, nice stay for the weekend."
United States
Dewey
$583 nightly
The price is $630
Sep 28 - Sep 29
Total with taxes and fees
Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace
A forested landscape with a wooden structure in the foreground.

10. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (33 reviews)
"Excellent stay"
United States
Laura S.
$323 nightly
The price is $348
Sep 27 - Sep 28
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A hot tub in a natural setting with a tree and a body of water in the background.

11. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (15 reviews)
"A nice relaxing spot."
United States
Darren F.
$339 nightly
The price is $380
Sep 27 - Sep 28
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
A wooden deck with a railing, a window, and a view of a forest.

12. Creekside Cabin with Hot Tub & Wood-Burning Stove

Creekside Cabin with Hot Tub & Wood-Burning Stove
Lanesville
9.8 out of 10, Exceptional, (14 reviews)
"The space is beautiful, well maintained and has everything you’d need to unwind and recharge. Highly recommend. "
United States
Gul R.
$503 nightly
The price is $543
Sep 30 - Oct 1
Total with taxes and fees
Creekside Cabin with Hot Tub & Wood-Burning Stove

13. 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.
$179 nightly
The price is $200
Sep 29 - Sep 30
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
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
9.8 out of 10, Exceptional, (7 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
$425 nightly
The price is $476
Sep 27 - Sep 28
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
A deck with outdoor furniture, a fire pit, and a covered area.

15. Catskills Cabin Saugerties HOT TUB + SAUNA Private Fully Fenced - Near Hiking

Catskills Cabin Saugerties HOT TUB + SAUNA Private Fully Fenced - Near Hiking
Saugerties
10.0 out of 10, Exceptional, (13 reviews)
"We loved our stay! The house had everything we needed and it was a great location!"
United States
Allison K.
Catskills Cabin Saugerties HOT TUB + SAUNA Private Fully Fenced - Near Hiking
A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, and an oven. There is a wooden ceiling and a blue rug on the floor.

16. Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter
9.6 out of 10, Exceptional, (13 reviews)
"Everything was great!"
United States
Samuel S.
$585 nightly
The price is $632
Sep 27 - Sep 28
Total with taxes and fees
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
A spacious living area with a large window, a ceiling fan, and a dining table set for four.

17. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
$620 nightly
The price is $669
Sep 27 - Sep 28
Total with taxes and fees
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

18. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$228 nightly
The price is $255
Oct 26 - Oct 27
Total with taxes and fees
Gatherwild Ranch
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bearsville Hotel Reviews

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"The room was spacious and clean, with a refrigerator, a coffee Maher and a microwave. The breakfast was nice, and the bar at the hotel was pleasant during the cocktail hour."
Elena 1-night trip
Posted 16 hours ago
Beekman Arms and Delamater Inn

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 $140 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.

Explore a world of travel with Expedia

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?

Catskill Cottage Walk to Downtown & River Views: This vacation home near Bearsville offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Bearsville?

Choose from 18 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 Ashokan Rail Trail- Woodstock Dike Trailhead and Opus 40.

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.