A river winding through a forested valley with autumn foliage.

Bearsville Holiday Rentals

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Our top choices for Bearsville holiday rentals

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.
The price is NZ$556
includes taxes & fees
27 Sept - 28 Sept
Streamside Cottage Half Mile to Town of Woodstock

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.
The price is NZ$1,126
includes taxes & fees
28 Sept - 29 Sept
Woodstock Historic Artist Estate - The Museum House

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.
The price is NZ$1,318
includes taxes & fees
28 Sept - 29 Sept
Cozy Mid-Century Retreat with Spa Hot Tub

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
The price is NZ$383
includes taxes & fees
26 Oct - 27 Oct
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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.
The price is NZ$473
includes taxes & fees
27 Sept - 28 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

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
The price is NZ$247
includes taxes & fees
28 Sept - 29 Sept
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
The price is NZ$958
includes taxes & fees
1 Oct - 2 Oct
Windham NY Escape

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.
The price is NZ$348
includes taxes & fees
5 Oct - 6 Oct
West Wing - a unique private space w/patio

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
The price is NZ$1,312
includes taxes & fees
27 Oct - 28 Oct
Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace

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.
The price is NZ$651
includes taxes & fees
27 Sept - 28 Sept
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

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.
The price is NZ$708
includes taxes & fees
27 Sept - 28 Sept
Peaceful Riverfront Cottage with Private Hot tub

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.
The price is NZ$1,024
includes taxes & fees
30 Sept - 1 Oct
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.
The price is NZ$358
includes taxes & fees
29 Sept - 30 Sept
Woods Cabin-Kingston/Woodstock, NY.

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
The price is NZ$898
includes taxes & fees
28 Sept - 29 Sept
Umana's Cabin, cozy, comfy, 5+ acres of land

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

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.
The price is NZ$1,175
includes taxes & fees
27 Sept - 28 Sept
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

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.
The price is NZ$1,242
includes taxes & fees
27 Sept - 28 Sept
Catskill Mountain Hideaway with Amazing Hunter Mountain Views

18. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is NZ$480
includes taxes & fees
28 Sept - 29 Sept
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.
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Top Bearsville Hotel Reviews

Find out more about Bearsville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bearsville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Bearsville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Bearsville. Seeing all the best attractions is bound to make you fall in love with Bearsville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Bearsville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Bearsville?

Yes, there are holiday rentals close to the most popular sights in Bearsville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Bearsville has to offer?

Catskill Cottage Walk to Downtown & River Views: This holiday home rental outside of 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 holiday rentals will I find in Bearsville?

Choose from 18 Expedia holiday rentals in Bearsville for a memorable holiday.

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 wider area, you’ll find Ashokan Rail Trail- Woodstock Dike Trailhead and Opus 40.

What are holiday rentals like in Bearsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bearsville. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.