Skip to content
34 stays

Stays in selected map area

Check travel restrictions before booking.
Please review and follow government travel guidelines.
Learn more
SUPERHOST
Entire house in Chester
Riverfront Getaway
4 guests2 bedrooms2 beds1 bath
WifiSelf check-inHot tubKitchen
Rating 4.96 out of 5;139 reviews
Price:$ 135 / night
SUPERHOST
Entire guest suite in Otis
Studio apartment the Rodeo Room
2 guests1 bedroom1 bed1 bath
Air conditioningWifiFree parking
Rating 4.88 out of 5;43 reviews
Price:$ 73 / night
Entire cottage in Chester
Brookside Cottage in historic Chester Village.
4 guests2 bedrooms2 beds1 bath
Air conditioningWifiSelf check-inKitchen
Rating 4.72 out of 5;58 reviews
Price:$ 107 / night
Entire cabin in East Otis
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
4 guests2 bedrooms3 beds1 bath
KitchenFree parkingIndoor fireplacePets allowed
Rating 4.67 out of 5;9 reviews
Price:$ 100 / night
Tent in Chester
Tentrr Partner Site - Glamping in Hephzibah
4 guests1 bedroom1 bed1 bath
Free parkingPets allowed
Rating 4.89 out of 5;19 reviews
Price:$ 133 / night
SUPERHOST
Entire apartment in Chester
Quite getaway in the Berkshires
6 guests3 bedrooms3 beds2 baths
WifiKitchenFree parkingWasher
Rating 5.0 out of 5;4 reviews
Price:$ 85 / night
SUPERHOST
Entire guest suite in Chester
Guest Suite in a Green Farmhouse
6 guests1 bedroom4 beds1 bath
Air conditioningBreakfastWifiSelf check-in
Rating 5.0 out of 5;21 reviews
Price:$ 100 / night
SUPERHOST
Entire house in Chester
Haley House
8 guests4 bedrooms4 beds2 baths
Air conditioningWifiSelf check-inKitchen
Rating 5.0 out of 5;52 reviews
Price:$ 200 / night
Entire cottage in Otis
NEW! East Otis Romantic Escape w/ Shared Dock!
4 guestsStudio2 beds1 bath
WifiKitchenFree parking
Price:$ 127 / night
SUPERHOST
Entire house in Russell
South Quarter House
8 guests3 bedrooms5 beds2 baths
Air conditioningWifiSelf check-inKitchen
Rating 4.96 out of 5;127 reviews
Price:$ 185 / night
SUPERHOST
Farm stay in East Otis
East Otis Rentals cozy and private
4 guests1 bedroom3 beds1 bath
Air conditioningWifiKitchenFree parking
Rating 4.74 out of 5;84 reviews
Price:$ 132 / night
Private room in Becket
Farmhouse Suite on Berkshire Farm
2 guests1 bedroom1 bed1 private bath
Self check-inFree parking
Rating 4.97 out of 5;94 reviews
Price:$ 75 / night
SUPERHOST
Entire house in Otis
Idyllic family retreat - spacious lake home,
8 guests4 bedrooms5 beds2.5 baths
WifiSelf check-inWaterfrontKitchen
Rating 4.90 out of 5;63 reviews
Price:$ 266 / night
Entire house in Becket
Charming Home Nestled in the Berkshires
6 guests3 bedrooms4 beds4 baths
Air conditioningWifiKitchenFree parking
Rating 4.79 out of 5;24 reviews
Price:$ 250 / night
SUPERHOST
Entire apartment in Otis
The front apartment of East Otis Rentals
5 guests1 bedroom3 beds2 baths
WifiKitchenFree parkingPets allowed
Rating 4.89 out of 5;48 reviews
Price:$ 125 / night
Entire house in Becket
Two bedroom house with a porch and a deck
6 guests2 bedrooms4 beds1 bath
Air conditioningWifiKitchenFree parking
Rating 4.0 out of 5;6 reviews
Price:$ 137 / night
SUPERHOST
Entire apartment in Otis
Star gazing in the Berkshires
6 guests2 bedrooms4 beds1 bath
Air conditioningBreakfastWifiKitchen
Rating 4.57 out of 5;7 reviews
Price:$ 140 / night
SUPERHOST
Entire cabin in Becket
Waldtreff - quiet grand cabin
10 guests3 bedrooms6 beds4 baths
WifiGymHot tubKitchen
Rating 5.0 out of 5;160 reviews
Price:$ 250 / night
Entire house in Becket
Berkshires retreat: warm & cozy in the woods!
8 guests3 bedrooms6 beds2 baths
WifiSelf check-inKitchenFree parking
Rating 4.80 out of 5;5 reviews
Price:$ 100 / night
Tent in Worthington
Tentrr Signature Site - Tamarack at Running Fox Berry Farm
6 guests1 bedroom1 bed1 bath
Free parkingPets allowed
Price:$ 115 / night
1 20 of 34 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.