Bearsville Holiday Rentals

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Holiday Rentals in Bearsville

Woodstock Ski House on 35 private acres Mtn Views

Woodstock Ski House on 35 private acres Mtn Views

10.0 out of 10, Exceptional, (44)
"Beautiful property, serene destination and a very well appointed house! We slept well in the comfortable beds and the kitchen had all we needed to cook a full meal! The nearby Woodstock downtown has plenty to visit as well."
Woodstock Ski House on 35 private acres Mtn Views
Starlite Motel
Exterior

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (244)
"Cosy room, clean bathroom, useable kitchen with all useful appliances. Loved the back yard with the fire pit. A little bit of a drive from our home but it was worth the effort. I would come again."
The price is AU$220
includes taxes & fees
2 Dec - 3 Dec
Starlite Motel
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AU$226
includes taxes & fees
11 Dec - 12 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Streamside Cottage Half Mile to Town of Woodstock
Aerial view

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (224)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
The price is AU$539
includes taxes & fees
23 Dec - 24 Dec
Streamside Cottage Half Mile to Town of Woodstock
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Property grounds

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

10.0 out of 10, Exceptional, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Tuscan Year Round Beauty - Pickleball Court
Outdoor dining

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court
Cozy Relaxing Retreat in Saugerties, NY
Exterior

Cozy Relaxing Retreat in Saugerties, NY

10.0 out of 10, Exceptional, (42)
"Beautiful, relaxing stay at this home in Saugerties. We loved the private location yet very close to Woodstock and Saugerties. Nick’s communication was fantastic, responding quickly to our questions. Safe, easy, flexible check in and check out. Inside was mix of rustic cabin and modern appliances, super clean. 100% recommend to anyone. "
Cozy Relaxing Retreat in Saugerties, NY
The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (175)
"This property is amazing and was exactly what I was looking for! We stayed two nights and upon arriving Paul greeted us and was very kind and helpful. The house was clean and everything was as described. We really enjoyed our stay and will come again."
The Cabin at Chichester in the Catskills Mountains
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
Dining

Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub

9.2 out of 10, Wonderful, (15)
"We had a great stay here at woodside! The house was clean and cozy. The perfect long weekend stay for us and our dog. "
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
Terrace/patio

High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!

10.0 out of 10, Exceptional, (21)
"My friends and I were looking for a place for 8 of us to enjoy the weekend and it was awesome. The house location has one of the most beautiful sights of any VRBO house I've stayed at. Between the incredible audio systems, furniture layout, overall living room aesthetics, and living room windows designed to take advantage of the beautiful view, the interior was ideal for our group. The host was in constant communication with us and gave clear directions for entering and leaving the house. Highly...
High Point Mtn House ~ Celebrate Thanksgiving on the Mountain! Total privacy!
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (39)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is AU$435
includes taxes & fees
15 Dec - 16 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
Exterior

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

10.0 out of 10, Exceptional, (203)
"Very comfortab;e and cozy"
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The Studio at the Inn at High Falls
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (20)
"Fantastic stay in the campfire cottage! Every detail was taken care of, from extra toothpaste (I always forget mine!) to the Nespresso machine. Cottage was very clean and cozy, communication was excellent. Would definitely return!"
The price is AU$270
includes taxes & fees
1 Dec - 2 Dec
Campfire Cottage: Fireplace, fire pit & no chores!
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

9.8 out of 10, Exceptional, (129)
"Escaped Long Island’s noise, traffic and overall stress . Listened to owls, watched birds soaring, kicked up leaves and gazed at the periwinkle colored mountains while perched on a bench. Felt safe enough knowing civilization was near enough, would have liked a landline phone just in case of an emergency "
Charming Artist's Retreat
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

9.6 out of 10, Exceptional, (45)
"We really enjoyed our stay in Hunter. The house met our needs well for a large family gathering. The hot tub and game room were excellent. Beutiful inside.It is close to shopping and hiking trails in the area. We did a lot of cooking and could have used larger cutting boards and baking/roasting pans. Be aware that the house is right on the main road into Hunter. The pinball machine was frustrating at times because the ball would get stuck.Overall it was a great stay."
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor dining

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (171)
"Everything was just perfect. The house was spacious and had so many wonderful amenities. Location was great, private and quiet. We enjoyed the hot tub under the stars each night to relax from the hiking! Highly recommend. "
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
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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Other types of properties in Bearsville you may be interested in

Best Western Plus Kingston Hotel And Conference Center
Indoor pool

Best Western Plus Kingston Hotel And Conference Center

2.5 star property
8.0 out of 10, Very good, (1071)
"I like it!"
The price is AU$226
includes taxes & fees
9 Dec - 10 Dec
Best Western Plus Kingston Hotel And Conference Center
Hunter Lodge, a Bluebird by Lark
Lobby sitting area

Hunter Lodge, a Bluebird by Lark

3.0 star property
9.2 out of 10, Wonderful, (529)
"Property smells amazing "
The price is AU$306
includes taxes & fees
1 Dec - 2 Dec
Hunter Lodge, a Bluebird by Lark
AutoCamp Catskills
Premium bedding, down duvets, Tempur-Pedic beds, individually decorated

AutoCamp Catskills

5.0 star property
9.0 out of 10, Wonderful, (332)
"Love the place, Love the people "
The price is AU$362
includes taxes & fees
1 Dec - 2 Dec
AutoCamp Catskills
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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?

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter: This holiday home rental outside of Bearsville is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Bearsville?

Choose from 17 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 Straus Center - Frost Valley YMCA, or get out into nature at a spot like Catskill Mountains. In the wider area, you’ll find Hunter Mountain and Overlook Mountain Trailhead.

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.