Skip to content
300+ stays

Stays in Bearsville

Enter dates and number of guests to see the total price per night.
Check travel restrictions before booking.
Please review and follow government travel guidelines.
Learn more
SUPERHOST
Entire guesthouse in Bearsville, Woodstock
Stylish Woodstock Guest House..Mountain Views
3 guests1 bedroom2 beds1 bath
WifiAir conditioningFree parking
Rating 4.96 out of 5;291 reviews
SUPERHOST
Entire cabin in Woodstock
Woodstock cabin 3 miles from town
2 guestsStudio0 beds1 bath
WifiKitchenFree parking
Rating 4.89 out of 5;177 reviews
Entire cabin in Bearsville
Watson Woods Cabin
4 guests2 bedrooms2 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;3 reviews
SUPERHOST
Entire cottage in Woodstock
Cozy Woodstock cottage
2 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.93 out of 5;205 reviews
SUPERHOST
Entire cabin in Willow
Romantic Cabin Nestled in the Woods
4 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.90 out of 5;58 reviews
SUPERHOST
Entire guest suite in Hurley
The Fifth Element - cute apt in the Catskills
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parking
Rating 4.93 out of 5;28 reviews
PLUS
Entire house in Woodstock
Woodstock Historic Artist Estate - The Pond House
5 guests3 bedrooms3 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.90 out of 5;81 reviews
SUPERHOST
Entire guesthouse in Bearsville
Relax on the Ridge - 2 miles from Woodstock
4 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 4.98 out of 5;209 reviews
SUPERHOST
Entire cabin in Woodstock
Byrdcliffe Artist Studio
4 guestsStudio3 beds1 bath
WifiKitchenFree parking
Rating 4.92 out of 5;248 reviews
PLUS
Entire guesthouse in Woodstock
Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace
2 guestsStudio1 bed1 bath
WifiKitchenFree parking
Rating 4.92 out of 5;143 reviews
SUPERHOST
Entire bungalow in Woodstock
Woodstock Charmer
6 guests3 bedrooms5 beds1 bath
WifiKitchenFree parking
Rating 4.91 out of 5;108 reviews
SUPERHOST
Entire cottage in Woodstock
Grapevine Cottage
2 guests1 bedroom2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.99 out of 5;141 reviews
SUPERHOST
Entire guest suite in Woodstock
Perfect Woodstock Location- Short Walk to Town
2 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 4.96 out of 5;108 reviews
SUPERHOST
Entire cottage in Woodstock
Romantic Cottage on the Stream, Walk to Town
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parking
Rating 4.95 out of 5;102 reviews
SUPERHOST
Tent in Bearsville
Glamping in Garden Paradise!
2 guests1 bedroom1 bed1 bath
WifiFree parking
Rating 5.0 out of 5;5 reviews
SUPERHOST
Entire cottage in Woodstock
Secluded Farmhouse Style, Close to All
4 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.96 out of 5;50 reviews
PLUS
Entire house in Woodstock
Woodstock Historic Artist Estate - Cottage House
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.86 out of 5;311 reviews
SUPERHOST
Entire house in Woodstock
Woodstock Mediterranean Retreat
10 guests4 bedrooms7 beds3 baths
WifiAir conditioningKitchenFree parking
Rating 4.80 out of 5;92 reviews
SUPERHOST
Entire house in Woodstock
Rocking Woodstock House on 4 acres with a Pond!
6 guests3 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.85 out of 5;67 reviews
SUPERHOST
Entire house in Woodstock
Modern Woodstock House in the Trees
8 guests4 bedrooms8 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.86 out of 5;89 reviews
120 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.