Chalets in Hampshire County

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Top Cities in Hampshire County

Main Street Stroll
ChaletsChalets

Northampton

Northampton

Chalets in Hampshire County

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. "
Little Longbow Lakefront Chalet
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
3 bedrooms, desk, iron/ironing board, travel crib

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!
Outdoor pool

Rustic Chalet at Camp Coldbrook!

Rustic Chalet at Camp Coldbrook!
Secluded Mountain Chalet
Interior

Secluded Mountain Chalet

10.0 out of 10, Exceptional, (2)
"We had a wonderful time - delightfully snowy and the house was quiet and cozy."
Secluded Mountain 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free