Over 1,000 places

Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
Apr 19 – 24
4.62 out of 5 average rating, 262 reviews
Guest favorite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
5 beds
Apr 20 – 25
4.88 out of 5 average rating, 189 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
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 New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
Apr 21 – 26
4.95 out of 5 average rating, 184 reviews
Guest favorite
Guest suite in Stockbridge
Private Stockbridge Getaway
2 queen beds
Apr 21 – 26
4.96 out of 5 average rating, 49 reviews
Guest favorite
Home in Stockbridge
Lake House on Stockbridge Bowl
6 beds
Apr 21 – 26
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Lenox
Berkshire, MA Getaway! Mile to town
3 queen beds
Apr 28 – May 3
4.86 out of 5 average rating, 328 reviews
Guest favorite
Guest suite in Lenox
T’Other House
1 queen bed
Apr 21 – 26
4.96 out of 5 average rating, 168 reviews
Guest favorite
Guesthouse in Lenox
Modern Barn with Loft at House on Golden Hill
3 beds
May 12 – 17
4.93 out of 5 average rating, 121 reviews
Guest favorite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
3 beds
May 1 – 6
5.0 out of 5 average rating, 21 reviews
Guest favorite
Guesthouse in Lenox
The Granary at House on Golden Hill
2 beds
Jun 1 – 6
4.95 out of 5 average rating, 276 reviews
Home in West Stockbridge
Wellspring by AvantStay | Indoor Pool + Views
9 beds
Apr 25 – 30
5.0 out of 5 average rating, 12 reviews
Guest favorite
Guesthouse in Stockbridge
Modern barn in the heart of the Berkshires
2 queen beds
Apr 29 – May 4
4.92 out of 5 average rating, 86 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr 19 – 24
4.99 out of 5 average rating, 105 reviews
Guest favorite
Home in West Stockbridge
Heart of the Berkshires - Bright, Cozy, Near Lake
5 beds
Apr 19 – 24
5.0 out of 5 average rating, 54 reviews
Guest favorite
Home in Richmond
Minutes to Tanglewood with massive yard
7 beds
Apr 21 – 26
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4 beds
May 27 – Jun 1
5.0 out of 5 average rating, 228 reviews