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Featured Chalets in Western Massachusetts

Sunny Chalet Nestled in the Woods of Ashfield
Interior

Sunny Chalet Nestled in the Woods of Ashfield

9.6 out of 10, Exceptional, (18)
"We were all very rested and relaxed. We enjoyed the beautiful spaces to sit and enjoy each other’s company. The chalet, flowers and setting made a terrific base to come and go from as we celebrated a family wedding."
Sunny Chalet Nestled in the Woods of Ashfield
Little Longbow Lakefront Chalet
Smart TV, fireplace

Little Longbow Lakefront Chalet

9.4 out of 10, Exceptional, (13)
"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "
The price is NZ$1,173
includes taxes & fees
29 July - 30 July
Little Longbow Lakefront Chalet
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
3 bedrooms, desk, iron/ironing board, travel cot

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
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 Western Massachusetts Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"The hotel was very unique as there was art spaces in the lobby. Liked that the room had lvp flooring. "
stephen 2-night trip
Posted 19 hours ago
Hotel Downstreet, Ascend Hotel Collection