Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Bearsville
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
New York
New York
Europe
Europe
Canada
Canada
Caribbean
Caribbean
Italy
Italy
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Gift cards
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Countryside
Skiing
Lake
Cabins
Amazing views
Amazing pools
Farms
Rooms
Chef's kitchens
Play
Tiny homes
Ski-in/out
Design
Lakefront
Trending
Vineyards
Bed & breakfasts
Off-the-grid
Barns
Camping
A-frames
Grand pianos
New
Mansions
Creative spaces
Yurts
Domes
Treehouses
Golfing
Beach
Beachfront
Filters
0
Display total before taxes
Show map
Search results; Over 1,000 places in Bearsville
Over 1,000 places in Bearsville
Guest favorite
Guest favorite
Guesthouse in Bearsville, Woodstock
Stylish Woodstock Guest House..Mountain View
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$195
night
$195 per night
4.95 out of 5 average rating, 418 reviews
4.95 (418)
Guest favorite
Guest favorite
Cabin in Bearsville
1970s Creekside Cabin | 2 miles from Woodstock
2 king beds
2 king beds
Apr 21 – 26
Apr 21 – 26
$720
$554
night
$554 per night, originally $720
4.96 out of 5 average rating, 140 reviews
4.96 (140)
Guest favorite
Guest favorite
Cottage in Bearsville
Mid-Century Artist Cottage
5 beds
5 beds
Apr 22 – 27
Apr 22 – 27
$229
night
$229 per night
4.9 out of 5 average rating, 39 reviews
4.9 (39)
Guest favorite
Guest favorite
Guesthouse in Bearsville
Relax on the Ridge - 2 miles from Woodstock
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$180
night
$180 per night
4.98 out of 5 average rating, 465 reviews
4.98 (465)
Guest favorite
Guest favorite
Guesthouse in Bearsville
Mt. Guardian Guest House Exquisite Mountain Views
1 queen bed
1 queen bed
May 27 – Jun 1
May 27 – Jun 1
$162
night
$162 per night
4.98 out of 5 average rating, 564 reviews
4.98 (564)
Guest favorite
Guest favorite
Cottage in Bearsville
Mirror Moon Cottage (waterfront)
2 beds
2 beds
May 22 – 27
May 22 – 27
$243
night
$243 per night
4.98 out of 5 average rating, 145 reviews
4.98 (145)
Guest favorite
Guest favorite
Cottage in Bearsville
Coldbrook Cottage
1 king bed
1 king bed
Apr 29 – May 4
Apr 29 – May 4
$178
night
$178 per night
4.99 out of 5 average rating, 141 reviews
4.99 (141)
Superhost
Superhost
Apartment in Woodstock
Hotel Woodstock - Aster Suite
1 queen bed
1 queen bed
Apr 20 – 25
Apr 20 – 25
$85
$77
night
$77 per night, originally $85
4.87 out of 5 average rating, 416 reviews
4.87 (416)
Guest favorite
Guest favorite
Home in Bearsville
Vredenburgh Farm
4 queen beds
4 queen beds
Apr 21 – 26
Apr 21 – 26
$350
night
$350 per night
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Guest favorite
Guest favorite
Home in Bearsville
Farmhouse w/ big yard + creek, mins from Woodstock
5 beds
5 beds
Apr 22 – 27
Apr 22 – 27
$380
$309
night
$309 per night, originally $380
4.98 out of 5 average rating, 48 reviews
4.98 (48)
Home in Bearsville
Woodstock Getaway - Family Friendly Home with Pool
3 beds
3 beds
Apr 24 – 29
Apr 24 – 29
$300
night
$300 per night
Guest favorite
Guest favorite
Cabin in Woodstock
Byrdcliffe Artist Studio (27.1-1-70)
3 beds
3 beds
Apr 22 – 27
Apr 22 – 27
$215
night
$215 per night
4.93 out of 5 average rating, 613 reviews
4.93 (613)
Home in Woodstock
Fiber Artist's Studio
3 beds
3 beds
Apr 20 – 25
Apr 20 – 25
$250
night
$250 per night
New place to stay
New
Home in Woodstock
The Bearsville Retreat
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$500
night
$500 per night
Guest favorite
Guest favorite
Guesthouse in Woodstock
Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star
4 beds
4 beds
May 12 – 17
May 12 – 17
$189
night
$189 per night
5.0 out of 5 average rating, 297 reviews
5.0 (297)
Guest favorite
Guest favorite
Cottage in Bearsville
Contemporary Guesthouse with Beautiful Views
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$250
night
$250 per night
4.98 out of 5 average rating, 97 reviews
4.98 (97)
Superhost
Superhost
Home in Bearsville
little owl mountain hideaway rest-hike-play-swim
4 beds
4 beds
Jul 8 – 13
Jul 8 – 13
$650
night
$650 per night
New place to stay
New
Superhost
Superhost
Home in Woodstock
Luxury Woodstock Retreat: 11 Acres of Bliss w Pool
4 beds
4 beds
May 27 – Jun 1
May 27 – Jun 1
$1,147
$803
night
$803 per night, originally $1,147
1
2
3
4
…
15