%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Display total before taxes

Search results; Over 1,000 rooms

Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
1 queen bed
May 5 – 10
4.93 out of 5 average rating, 255 reviews
Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
2 beds
May 19 – 24
4.94 out of 5 average rating, 347 reviews
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
3 beds
Apr 22 – 27
4.9 out of 5 average rating, 202 reviews
Guest favorite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
May 5 – 10
5.0 out of 5 average rating, 226 reviews
Cabin in Monterey
Secluded cabin with babbling brook
3 beds
Apr 26 – May 1
4.86 out of 5 average rating, 196 reviews
Guest favorite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
1 queen bed
May 6 – 11
5.0 out of 5 average rating, 43 reviews
Guest favorite
Apartment in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 bed
May 5 – 10
5.0 out of 5 average rating, 15 reviews
Guest favorite
Guesthouse in Stockbridge
Modern studio with views of the treetops
2 beds
Apr 22 – 27
4.96 out of 5 average rating, 175 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Apr 20 – 25
4.99 out of 5 average rating, 105 reviews
Guest favorite
Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
1 queen bed
Apr 28 – May 3
4.95 out of 5 average rating, 182 reviews
Guest favorite
Cottage in Becket
Cozy lakeside cottage
3 beds
Jun 9 – 14
4.95 out of 5 average rating, 125 reviews
Guest favorite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 46 reviews
Guest favorite
Apartment in Canaan
Queechy Lake Carriage House
2 beds
Apr 21 – 26
4.96 out of 5 average rating, 82 reviews
Guest favorite
Home in Becket
Berkshires Retreat W/ Sauna by Evergreen Home
7 beds
Apr 21 – 26
4.96 out of 5 average rating, 49 reviews
Guest favorite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
3 beds
May 2 – 7
5.0 out of 5 average rating, 65 reviews
Guest favorite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4 beds
Sep 8 – 13
4.94 out of 5 average rating, 90 reviews
Superhost
Apartment in Pittsfield
Cozy Chic - Studio Apartment
1 queen bed
May 6 – 11
New place to stay
Guest favorite
Guesthouse in Great Barrington
Sweet Victorian in Housatonic
6 beds
Apr 22 – 27
5.0 out of 5 average rating, 46 reviews