Holiday Homes in Bearsville

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Our top choices for Bearsville holiday homes

1. Woodstock Historic Artist Estate - The Carriage House

Woodstock Historic Artist Estate - The Carriage House
Woodstock
9.8 out of 10, Exceptional, (51 reviews)
"We had a wonderful time, again! Perfect location!"
United States
Fran W.
The price is AU$694
includes taxes & fees
10 Nov - 11 Nov
Woodstock Historic Artist Estate - The Carriage House

2. Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!
Woodstock
9.0 out of 10, Wonderful, (2 reviews)
"Great location."
United States
Louis
The price is AU$462
includes taxes & fees
10 Nov - 11 Nov
Hidden Pines - Spacious Charming One Bedroom Woodstock Cottage, Walk to Town!

3. 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.
The price is AU$714
includes taxes & fees
15 Nov - 16 Nov
A pleasant space in a pleasant neighborhood in a beautiful part of the country!

4. Butterfly Bungalow Studio · Saugerties/Woodstock

Butterfly Bungalow Studio · Saugerties/Woodstock
Saugerties
10.0 out of 10, Exceptional, (2 reviews)
"Great location, had everything needed for a comfortable stay."
United States
Michael W.
The price is AU$332
includes taxes & fees
7 Dec - 8 Dec
Butterfly Bungalow Studio · Saugerties/Woodstock

5. Butterfly and Sage: 2 Studios, Shared Yard

Butterfly and Sage: 2 Studios, Shared Yard
Saugerties
The price is AU$571
includes taxes & fees
3 Dec - 4 Dec
Butterfly and Sage: 2 Studios, Shared Yard

6. 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.
The price is AU$355
includes taxes & fees
18 Nov - 19 Nov
Campfire Cottage: Fireplace, fire pit & no chores!

7. 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, (110 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is AU$388
includes taxes & fees
10 Nov - 11 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

8. 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, (7 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.
The price is AU$349
includes taxes & fees
12 Nov - 13 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

9. Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
9.8 out of 10, Exceptional, (16 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 AU$1,010
includes taxes & fees
11 Nov - 12 Nov
Woodstock Historic Artist Estate - The Museum House

10. 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 AU$1,026
includes taxes & fees
22 Nov - 23 Nov
Cozy Mid-Century Retreat with Spa Hot Tub

11. 2BR Barnhouse Horse Farm Views by hiking, Phoenicia, Hunter

2BR Barnhouse Horse Farm Views by hiking, Phoenicia, Hunter
Hunter
9.8 out of 10, Exceptional, (9 reviews)
"Great host. Very quiet place to relax."
United States
Evan H.
The price is AU$424
includes taxes & fees
10 Nov - 11 Nov
2BR Barnhouse Horse Farm Views by hiking, Phoenicia, Hunter

12. 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
The price is AU$417
includes taxes & fees
18 Nov - 19 Nov
Retro Retreat: renovated 2BR, desk, no chore list!

13. Hot Tub, Fireplace, Close To Woodstock

Hot Tub, Fireplace, Close To Woodstock
West Hurley
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful place! "
United States
Cheryl U.
The price is AU$1,371
includes taxes & fees
10 Nov - 11 Nov
Hot Tub, Fireplace, Close To Woodstock

14. Woodstock historic artist estate - The Pond House

Woodstock historic artist estate - The Pond House
Woodstock
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful host, outstanding location, very nice and creative home. We very much enjoyed our stay, and look forward to coming back again!"
United States
Joe V.
The price is AU$1,433
includes taxes & fees
15 Nov - 16 Nov
Woodstock historic artist estate - The Pond House

15. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (17 reviews)
"A nice relaxing spot."
United States
Darren F.
The price is AU$630
includes taxes & fees
23 Nov - 24 Nov
Peaceful Riverfront Cottage with Private Hot tub

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, (42 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.
The price is AU$523
includes taxes & fees
7 Dec - 8 Dec
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

17. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 10, Exceptional, (1 review)
"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"
United States
Laura D.
The price is AU$686
includes taxes & fees
10 Nov - 11 Nov
Historic Cottage * Steam Shower * Chef’s Kitchen

18. Hot Tub * Fireplace * Near Woodstock

Hot Tub * Fireplace * Near Woodstock
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Perfect spot in Saugerties/Woodstock area. Very helpful communication with property management. Looking forward to staying again sometime!"
United States
Theodore F. L.
The price is AU$1,223
includes taxes & fees
10 Nov - 11 Nov
Hot Tub * Fireplace * Near Woodstock

19. Mid-Century Ranch, One-Level Living, Quiet Garden

Mid-Century Ranch, One-Level Living, Quiet Garden
Olivebridge
The price is AU$850
includes taxes & fees
16 Nov - 17 Nov
Mid-Century Ranch, One-Level Living, Quiet Garden

20. The Bend: Meadow Suite • Pool • Sauna • Fire Pits

The Bend: Meadow Suite • Pool • Sauna • Fire Pits
Phoenicia
The price is AU$689
includes taxes & fees
16 Nov - 17 Nov
The Bend: Meadow Suite • Pool • Sauna • Fire Pits
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.

Learn more about Bearsville

Venture to Bearsville Theater and Overlook Mountain Trailhead—just two of the sights around Bearsville.

A river winding through a forested valley with autumn foliage.

Top reviews in Bearsville