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Search results; Over 1,000 homes in Bearsville, Woodstock

Top guest favorite
Look out over the Catskills from this 1920s converted barn in Woodstock
1 bedroom, 2 beds, 1 private bath
Sep 7 – 12
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4.95 out of 5 average rating, 472 reviews
Top guest favorite
Sweeping views greet you at this hilltop Woodstock guesthouse on 5+ acres
4.98 out of 5 average rating, 600 reviews, 1 bedroom, 2 beds, 1 bath
Aug 17 – 22
Top guest favorite
Fall asleep to the Saw Kill at this waterfront Woodstock cottage in the woods
4.96 out of 5 average rating, 262 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 31 – Sep 5
Guest favorite
This restored 1889 Bearsville barn gives you a fenced pool, fire pit, and pizza oven
4.94 out of 5 average rating, 35 reviews, 4 bedrooms, 4 beds, 2 baths
Sep 5 – 10
Guest favorite
An 1875 colonial farmhouse on 2 acres where you’ll find 3 porches and a fire pit in Woodstock
4.92 out of 5 average rating, 65 reviews, 4 bedrooms, 4 beds, 2 baths
Aug 17 – 22
Guest favorite
Wake to mountain views and a barrel sauna at this 1909 Woodstock cabin
4.83 out of 5 average rating, 219 reviews, 1 bedroom, 1 bed, 1 bath
Aug 18 – 23
Top guest favorite
Private room
Award-winning gardens and a heated pool greet you at this Woodstock home
4.98 out of 5 average rating, 40 reviews, 1 queen bed, 1 bath
Aug 30 – Sep 4
Top guest favorite
This wooded Woodstock house puts you one mile from the village
4.99 out of 5 average rating, 77 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Wake to meadow and mountain views from this secluded Bearsville cottage on 13 acres
4.97 out of 5 average rating, 144 reviews, 1 bedroom, 1 bed, 1 bath
Sep 9 – 14
Top guest favorite
Gaze up through the skylight at this secluded Woodstock guesthouse with mountain views
4.98 out of 5 average rating, 636 reviews, 1 bedroom, 1 bed, 1 bath
Nov 1 – 6
Top guest favorite
Private room
Spectacular views and a pool on 17 acres at this mid-century Byrdcliffe home
4.93 out of 5 average rating, 469 reviews, 1 bed, 1 bath
Sep 21 – 26
Top guest favorite
Sip coffee by Tannery Brook at this 1880 Woodstock barn with a fire pit
4.91 out of 5 average rating, 529 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
This 1970s log cabin in Bearsville gives you a stone fireplace, stream, and woods
4.97 out of 5 average rating, 166 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 19 – 24
Top guest favorite
This 1950s Bauhaus bungalow in Woodstock puts you fireside in the woods
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 22 – 27
Top guest favorite
Mountain views greet you from this secluded Woodstock log cabin on 15 acres
5.0 out of 5 average rating, 30 reviews, 3 bedrooms, 5 beds, 1.5 baths
Sep 4 – 9
This newly renovated Woodstock guesthouse gives you cathedral ceilings and a private yard
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bath
Aug 31 – Sep 5
Top guest favorite
This historic artist cabin in Woodstock puts you deep in the Catskill Forest
4.93 out of 5 average rating, 869 reviews, 3 beds, 1 bath
Sep 7 – 12
Top guest favorite
This private Olive cottage gives you 2 wooded acres and a fireplace
4.99 out of 5 average rating, 234 reviews, 1 bedroom, 1 bed, 1 bath
Sep 13 – 18
Guest favorite
This off-grid Catskills cabin puts you by an ephemeral pond in deep forest
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 1 bed, 1 bath
Sep 23 – 28