Bearsville Vacation Rentals from CA $200: Short-Term Rentals for 2026

Q: 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.

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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

Woodstock

Kristen S.

CA $498 total

includes taxes & fees

Oct 20 - Oct 21

A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

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

Kingston

Chris L.

CA $381 total

includes taxes & fees

Oct 22 - Oct 23

A wooden deck with a bench, surrounded by a forested area.

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

Shokan

MIKE W.

CA $283 total

includes taxes & fees

Oct 6 - Oct 7

4. Woods Cabin-Kingston/Woodstock, NY.

Kingston

"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...

Michael H.

CA $286 total

includes taxes & fees

Oct 6 - Oct 7

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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

Catskill

Yeudin

CA $309 total

includes taxes & fees

Nov 3 - Nov 4

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

Big Indian

Sarah

CA $200 total

includes taxes & fees

Oct 6 - Oct 7

An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

7. Cozy Mid-Century Retreat with Spa Hot Tub

Woodstock

Alec M.

CA $1,071 total

includes taxes & fees

Oct 7 - Oct 8

A modern kitchen with a central island, black cabinetry, and pendant lighting.

8. Woodstock Historic Artist Estate - The Museum House

Woodstock

Strati P.

CA $920 total

includes taxes & fees

Oct 6 - Oct 7

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Top Bearsville Hotel Reviews

Hotel Vienna

8/10 Good

"Very clean and well kept place. The pool area is lovely as well. The breakfast was mostly sugar stuff though… with lots of pastries and sweetened yogurts, and only caffeinated coffee available. Be sure to prepare accordingly if you have dietary restrictions. We enjoyed our stay and the location."

Urban Cowboy Lodge

8/10 Good

"The room was clean but a little smaller than we anticipated. Was hard to tell online. We did a tour of other available rooms would definitely choose differently next time. The property was amazing. We stayed during the week so it was so nice and quiet. We had the Japanese soaking tub which was great! We brought our dog and we were able to take her with us everywhere on the property. You’d never know that it was a pet friendly place as it is kept very clean. My ONLY negative comment would be that there is no where to get a meal that isn’t ridiculous expensive. I understand the limited menus in the area but everything was ridiculous expensive and very bougie food. Next time we would definitely pack some more snacks and food. Otherwise the place I awesome and worth the stay. We loved the robes! Wore them to our sauna appointment and then went and did a cold plunge in the river. So tranquil! We did not hook up the the WiFi so we stayed off grid for the three days we were there and that was just incredible. The staff were all super friendly and accommodating. What a fantastic place! Can’t wait to go back!"

New Paltz Way Hotel

8/10 Good

"The views and room design were beautiful, and we enjoyed the sauna and steam rooms. However, we expected the small indoor pool to feel more like a hot tub. The water was too cool for us to relax comfortably, although a staff member said the temperature was normal. Service also varied: the woman on the first day wasn’t very welcoming when we asked for coffee, while the man the next morning was warm and friendly. The New Paltz area is lovely for walks and a short getaway, but we would only consider staying again at a lower rate."

Find out more about Bearsville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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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Check prices for these dates

Our top choices for Bearsville vacation rentals

1. Streamside Cottage Half Mile to Town of Woodstock

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

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

4. Woods Cabin-Kingston/Woodstock, NY.

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

6. Starlite Motel

7. Cozy Mid-Century Retreat with Spa Hot Tub

8. Woodstock Historic Artist Estate - The Museum House

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

10. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

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

12. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

13. Jessie's Harvest House

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

15. 1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

16. Jessie's Harvest House Suite

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

18. Tannersville 1BR on Main Street, sleeps 3

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

20. Elegant Studio on Tannersville Main Street

Find vacation rentals that suit your style

Top Bearsville Hotel Reviews

Hotel Vienna

Super 8 by Wyndham Kingston

Howard Johnson by Wyndham Saugerties

Residence Inn by Marriott Kingston

Urban Cowboy Lodge

AutoCamp Catskills

New Paltz Way Hotel

Courtyard by Marriott Kingston

Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Bearsville

Frequently asked questions

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