Chalets in Massachusetts

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Chalets in Massachusetts

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
Sunny Chalet Nestled in the Woods of Ashfield
Relax in this inviting room with a brick fireplace, dining table, and comfortable seating area.

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
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
Rustic Chalet at Camp Coldbrook!
Relax by the pool surrounded by lush greenery and enjoy the serene atmosphere.

Rustic Chalet at Camp Coldbrook!

Rustic Chalet at Camp Coldbrook!
Beautifully handcrafted arts and craft style carriage house chalet
Stunning two-story home with a charming front porch and pitched roof.

Beautifully handcrafted arts and craft style carriage house chalet

3.0 star property
Beautifully handcrafted arts and craft style carriage house chalet
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 Massachusetts Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Everything was great"
Oleksandr 3-night trip
Posted 1 day ago
Omni Boston Hotel at the Seaport