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Search results; Over 1,000 places

Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
Apr 21 – 26
4.62 out of 5 average rating, 262 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
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
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 queen beds
Apr 21 – 26
5.0 out of 5 average rating, 18 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
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
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
1 bed
Apr 20 – 25
4.99 out of 5 average rating, 105 reviews
Superhost
Treehouse in New Marlborough
Double 3 Bedroom Tree House in the Berkshires
4 beds
May 5 – 10
4.92 out of 5 average rating, 84 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
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
Home in Stockbridge
Bright Stockbridge country home, near everything!
4 beds
Sep 8 – 13
4.94 out of 5 average rating, 90 reviews
Guest favorite
Guesthouse in Cornwall
Charming Guest Cottage with Private Pool
1 bed
May 12 – 17
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Becket
Little Longbow Lakefront Chalet
3 beds
Apr 21 – 26
4.91 out of 5 average rating, 54 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, 277 reviews
Guest favorite
Home in Becket
Lake front retreat - Stylish Berkshire home
5 beds
Apr 26 – May 1
4.93 out of 5 average rating, 118 reviews
Guest favorite
Guesthouse in Granby
Windy Top Cottage ~ A Romantic "European" Getaway
2 beds
Jul 14 – 19
4.99 out of 5 average rating, 704 reviews
Guest favorite
Cottage in Great Barrington
Cozy Country Cottage w Fireplace
1 queen bed
Apr 21 – 26
4.95 out of 5 average rating, 76 reviews