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119 properties are available in and around this destination

Great BarringtonShow on map
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining offers accommodations in Great Barrington, 11 miles from Norman Rockwell Museum and 14 miles from Cranwell Spa & Golf Club.
Great BarringtonShow on map
Cozy Great Barrington Home about 1 Mi to Ski Resort! is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tanglewood Musical Center.
Great BarringtonShow on map
East Rock Inn features air-conditioned rooms in Great Barrington. This recently renovated condo hotel is located 8.9 miles from Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club.
New MarlboroughShow on map
Waterfront Cottage 10 Min to Great Barrington! is located in New Marlborough, just 15 miles from Great Falls and 15 miles from Canaan Village Historic District.
New MarlboroughShow on map
Rustic Berkshires Cottage at Lake Buel with Kayaks! is located in New Marlborough, just 16 miles from Cranwell Spa & Golf Club and 16 miles from Tanglewood Musical Center.
New MarlboroughShow on map
Renovated Lakefront House with Dock Pets Welcome! is located in New Marlborough, just 16 miles from Tanglewood Musical Center and 16 miles from Tanglewood.
MontereyShow on map
Serene Monterey Home with Deck Near Skiing and Hiking! offers accommodations in Monterey, 15 miles from Cranwell Spa & Golf Club and 15 miles from Tanglewood Musical Center.
Great BarringtonShow on map
Beautiful Berkshires Cottage on Lake Buel is located in Great Barrington, just 13 miles from Norman Rockwell Museum and 16 miles from Cranwell Spa & Golf Club.
New to Booking.com
Great BarringtonShow on map
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town offers accommodations in Great Barrington, 8.9 miles from Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club.
Great BarringtonShow on map
Downtown Great Barrington Enjoy Mountain Views is located in Great Barrington, just 9.3 miles from Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club.
Great BarringtonShow on map
Spacious Berkshires Retreat about 3 Mi to Skiing! is located in Great Barrington, just 11 miles from Cranwell Spa & Golf Club and 11 miles from Tanglewood Musical Center.
Great BarringtonShow on map
NEW LISTING SPECIAL SAVE 10 Impeccable House Minutes from Downtown Great Barrington is located in Great Barrington, just 13 miles from Tanglewood Musical Center and 13 miles from Cranwell Spa & Golf...
Great BarringtonShow on map
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tanglewood Musical Center.
Great BarringtonShow on map
Private Home Overlooking Stevens Lake offers accommodations in Great Barrington, 16 miles from Tanglewood Musical Center and 17 miles from Tanglewood.
New MarlboroughShow on map
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 is located in New Marlborough, just 15 miles from Norman Rockwell Museum and 17 miles from Cranwell Spa & Golf Club.
Great BarringtonShow on map
7 miles from Norman Rockwell Museum in Great Barrington, Woodland Hills Modern Cottage Minutes from Downtown Great Barrington provides accommodations with access to a fitness room.
SheffieldShow on map
Whitney by AvantStay Private Berkshires Estate offers accommodations in Sheffield, 14 miles from Norman Rockwell Museum and 18 miles from Cranwell Spa & Golf Club.
Great BarringtonShow on map
Providing a garden, Magical Country Retreat in the Berkshires offers accommodations in Great Barrington. This property offers access to a terrace and free private parking.
Great BarringtonShow on map
Magical Country Retreat in the Berkshires offers accommodations in Great Barrington, 8 miles from Norman Rockwell Museum and 13 miles from Tanglewood Musical Center.
SheffieldShow on map
Waterview Home in the Berkshires Near Hiking is located in Sheffield, just 19 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center.
MontereyShow on map
Monterey Home with Hot Tub, Pool and Game Room! offers accommodations in Monterey, 14 miles from Norman Rockwell Museum and 15 miles from Tanglewood.
New to Booking.com
SheffieldShow on map
Featuring water sports facilities, The Freeman- 14K SF Estate 40acrs Tennis Vineyard provides accommodations in Sheffield. This property offers access to a terrace and free private parking.
MontereyShow on map
Hupi House - A Peaceful Wooded Lakeside Retreat is located in Monterey, just 13 miles from Cranwell Spa & Golf Club and 14 miles from Norman Rockwell Museum.
SheffieldShow on map
Summer and Fall in Sheffield with Monthly Special Pricing Available offers accommodations in Sheffield, 22 miles from Tanglewood Musical Center and 22 miles from Tanglewood.
North EgremontShow on map
Moose Lodge by AvantStay Luxe Berkshires Escape offers accommodations in North Egremont, 10 miles from Norman Rockwell Museum and 14 miles from Tanglewood Musical Center.