A river winding through a forested valley with autumn foliage.

Bearsville Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 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, (305 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.
$303 nightly
The price is $339
Nov 4 - Nov 5
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A building with a large window reflecting trees, a wooden exterior, and a yellow roof.

2. 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.
$443 nightly
The price is $490
Oct 21 - Oct 22
Total with taxes and fees
A pleasant space in a pleasant neighborhood in a beautiful part of the country!
A modern kitchen with a large island, a sink, and wooden stools.

3. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House
Woodstock
9.8 out of 10, Exceptional, (50 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
$573 nightly
The price is $642
Oct 26 - Oct 27
Total with taxes and fees
Woodstock Historic Artist Estate - The Carriage House
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, (322 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
$201 nightly
The price is $217
Nov 15 - Nov 16
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, (105 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
$213 nightly
The price is $239
Oct 30 - Oct 31
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A wooden deck with a bench, surrounded by a forested area.

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

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (37 reviews)
"loved our stay and would stay again!"
United States
MIKE W.
$187 nightly
The price is $210
Oct 22 - Oct 23
Total with taxes and fees
West Wing - a unique private space w/patio
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

7. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (316 reviews)
"Everything was great"
United States
Danielle
$145 nightly
The price is $162
Oct 19 - Oct 20
Total with taxes and fees
Starlite Motel
Private kitchen

8. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (14 reviews)
"Great little place! The cabin was very clean and sits in a great spot. Very relaxing place to pop off grid. Nothing fancy, but has everything you need."
United States
Connie K.
$181 nightly
The price is $203
Oct 20 - Oct 21
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A modern kitchen with a central island, black cabinetry, and pendant lighting.

9. 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.
$742 nightly
The price is $831
Oct 19 - Oct 20
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

10. 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.
$227 nightly
The price is $254
Nov 3 - Nov 4
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

11. 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.
$195 nightly
The price is $207
Nov 3 - Nov 4
Total with taxes and fees
Jessie's Harvest House
A forested landscape with a wooden structure in the foreground.

12. 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.
$345 nightly
The price is $372
Oct 18 - Oct 19
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

13. 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.
$253 nightly
The price is $286
Nov 3 - Nov 4
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A two-story house with a covered porch and a small deck.

14. Modern Main Street Studio in Tannersville

Modern Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (8 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
$216 nightly
The price is $233
Oct 20 - Oct 21
Total with taxes and fees
Modern Main Street Studio in Tannersville
An outdoor deck with a table and chairs, surrounded by trees and a wood-burning stove.

15. 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.
$766 nightly
The price is $858
Oct 21 - Oct 22
Total with taxes and fees
Cozy Mid-Century Retreat with Spa Hot Tub
A room with a wooden cabinet, a glass door leading to a closet, a blue patterned rug, and a wooden floor.

16. 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, (41 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.
$339 nightly
The price is $380
Oct 18 - Oct 19
Total with taxes and fees
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

17. 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.
$219 nightly
The price is $245
Nov 2 - Nov 3
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.

18. 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
$270 nightly
The price is $302
Nov 2 - Nov 3
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
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.

19. 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.
$239 nightly
The price is $268
Oct 22 - Oct 23
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
A hanging flower basket with purple and white flowers, a white fence, and a green lawn in the background.

20. Elegant Main Street Studio in Tannersville

Elegant Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (19 reviews)
"Great location."
United States
Edward P.
$234 nightly
The price is $252
Oct 20 - Oct 21
Total with taxes and fees
Elegant Main Street Studio in Tannersville
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"The room was huge and very roomy!!! We had a beautiful view of the mountains! We loved our stay and would love to return."
Debbie 3-night trip
Posted 7 hours ago
Hunter Lodge, a Bluebird by Lark

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.

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?

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.