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81 places to stay

SUPERHOST
Private room
Rating 5.0 out of 5;13 reviews
Sheffield Lodge - Taconic Room
2 guests1 bedroom2 beds1 shared bathroom
WifiIndoor fireplaceKitchenHeating
Private room
Beautiful Getaway in the Berkshire Mountains.
2 guests1 bedroom2 beds1.5 bathrooms
WifiIndoor fireplaceHeating
Entire guest suite
Rating 5.0 out of 5;76 reviews
Berkshire Mountain Views
2 guests1 bedroom1 bed1 bathroom
WifiIndoor fireplaceHeating
SUPERHOST
Entire cottage
Rating 4.85 out of 5;20 reviews
Cozy Ski Cottage near Catamount, Berkshires
5 guests2 bedrooms3 beds1.5 bathrooms
WifiIndoor fireplaceKitchenHeating
SUPERHOST
Entire cottage
Rating 4.89 out of 5;146 reviews
Beautiful cottage in Copake Falls
4 guests2 bedrooms2 beds1 bathroom
WifiKitchenHeating
SUPERHOST
Entire cottage
Rating 5.0 out of 5;22 reviews
Newly built cottage on working farm
4 guests1 bedroom2 beds1 bathroom
WifiKitchenHeating
Entire house
Rating 4.50 out of 5;42 reviews
★Beautiful Lakehouse with POOL TABLE★
10 guests3 bedrooms5 beds1.5 bathrooms
WifiKitchenHeating
SUPERHOST
Entire house
Rating 4.95 out of 5;95 reviews
Modern Farm House 5 minutes from Great Barrington
4 guests2 bedrooms2 beds2 bathrooms
WifiKitchenHeating
SUPERHOST
Entire house
Rating 4.92 out of 5;38 reviews
Modern Farmhouse Bungalow w Private Bridge & Brook
7 guests3 bedrooms5 beds2 bathrooms
WifiIndoor fireplaceKitchenHeating
Entire cabin
Rating 5.0 out of 5;3 reviews
Peaceful Lake Cabin on Robinson Pond
4 guests2 bedrooms4 beds1 bathroom
WifiIndoor fireplaceKitchenHeating
SUPERHOST
Entire cabin
Rating 5.0 out of 5;4 reviews
GORGEOUS BERKSHIRE/HUDSON VALLEY MOUNTAIN CABIN
6 guests3 bedrooms4 beds2 bathrooms
WifiIndoor fireplaceKitchenHeating
SUPERHOST
Entire cottage
Rating 4.75 out of 5;58 reviews
The Lakehouse at Robinson Pond
7 guests3 bedrooms6 beds2 bathrooms
WifiIndoor fireplaceKitchenHeating
Hotel room
Room 2 The October Room at The Windflower Inn
2 guests1 bedroom1 bed1 bathroom
WifiHeating
SUPERHOST
Entire cabin
Rating 5.0 out of 5;31 reviews
Sunset; private swimming-pool!(North Mtn Cottages)
10 guests3 bedrooms6 beds2 bathrooms
WifiKitchenHeating
Entire guest suite
Rating 4.70 out of 5;10 reviews
Fall/Winter Spa Sanctuary with Trail System
6 guests2 bedrooms3 beds1 bathroom
WifiKitchenHeating

Introducing Airbnb Adventures

Multi-day trips led by local experts – activities, meals, and stays included.
SUPERHOST
Entire house
Rating 4.82 out of 5;74 reviews
Modern Farmhouse near hiking, skiing & swimming
8 guests4 bedrooms4 beds2 bathrooms
WifiKitchenHeating
Entire house
Rating 4.42 out of 5;39 reviews
Gorgeous Farmhouse in Village
5 guests3 bedrooms3 beds1 bathroom
WifiIndoor fireplaceKitchenHeating
SUPERHOST
Private room
Rating 4.94 out of 5;16 reviews
Sheffield Lodge - Washington Room
2 guests1 bedroom1 bed1 shared bathroom
WifiIndoor fireplaceKitchenHeating
SUPERHOST
Private room
Rating 4.88 out of 5;25 reviews
Sheffield Lodge - Greylock Room
2 guests1 bedroom1 bed1 private bathroom
WifiIndoor fireplaceKitchenHeating
SUPERHOST
Private room
Rating 4.96 out of 5;24 reviews
Sheffield Lodge - Everett Room
2 guests1 bedroom1 bed1 shared bathroom
WifiKitchenHeating
120 of 81 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.