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Browse Select Great Barrington Chalets

Little Longbow Lakefront Chalet
Relax on the deck with a view of the lush landscape, featuring a comfortable sofa and outdoor seating area.

Little Longbow Lakefront Chalet

9.6 out of 10, Exceptional, (14)
"Our stay was great. The property was extremely clean and the host was absolutely amazing. The property is located on a pond which we could kayak and do some fishing. Just sitting on the beautiful deck overlooking the pond was relaxing. The property offered exactly what we were looking for for this trip. "
Little Longbow Lakefront Chalet
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
Two single beds with white duvets, a wooden staircase, and a large mirror adorn this inviting bedroom.

Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach

9.8 out of 10, Exceptional, (24)
"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
Majestic Lake Front Chalet
Relax in this spacious living room with a comfortable seating area, large windows, and a sloped ceiling.

Majestic Lake Front Chalet

2.0 star property
Majestic Lake Front Chalet
SRC-Hudson Valley/Berkshires Cultural Corridor
Situated on a hill, this house offers expansive views of the surrounding forested hills.

SRC-Hudson Valley/Berkshires Cultural Corridor

SRC-Hudson Valley/Berkshires Cultural Corridor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Barrington Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Amazing service and cheerful staff !!! Thanks so much "
Shaniqua 2-night trip
Posted 21 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG