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Search results; Over 1,000 places

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Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
20–25 Apr
4.62 out of 5 average rating, 262 reviews
Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
Individual Host
19–24 May
4.94 out of 5 average rating, 347 reviews
Guest favourite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Individual Host
22–27 Apr
4.9 out of 5 average rating, 202 reviews
Guest favourite
Flat in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Professional Host
5–10 May
4.93 out of 5 average rating, 255 reviews
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
Individual Host
5–10 May
5.0 out of 5 average rating, 226 reviews
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 bed
5–10 May
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
Professional Host
28 Apr – 3 May
4.95 out of 5 average rating, 182 reviews
Guest favourite
Cottage in Becket
Cozy lakeside cottage
Individual Host
27 May – 1 Jun
4.95 out of 5 average rating, 125 reviews
Guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
Individual Host
22–27 Apr
4.96 out of 5 average rating, 175 reviews
Guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
20–25 Apr
4.99 out of 5 average rating, 105 reviews
Guest favourite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
1 queen bed
6–11 May
5.0 out of 5 average rating, 43 reviews
Guest favourite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
Individual Host
21–26 Apr
5.0 out of 5 average rating, 46 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
6 beds
22–27 Apr
5.0 out of 5 average rating, 46 reviews
Superhost
Home in Becket
Tranquil 3-BR Waterfront Retreat
4 beds
23–28 Apr
4.89 out of 5 average rating, 44 reviews
Cabin in Monterey
Secluded cabin with babbling brook
Individual Host
26 Apr – 1 May
4.86 out of 5 average rating, 196 reviews
Superhost
Treehouse in New Marlborough
Double 3 Bedroom Tree House in the Berkshires
4 beds
5–10 May
4.92 out of 5 average rating, 84 reviews
Guest favourite
Home in Becket
Lake front retreat - Stylish Berkshire home
Individual Host
26 Apr – 1 May
4.93 out of 5 average rating, 118 reviews
Guest favourite
Guest house in Lenox
Modern Barn with Loft at House on Golden Hill
Individual Host
12–17 May
4.93 out of 5 average rating, 121 reviews