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Search results; Over 1,000 places

Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
21–26 Apr
4.62 out of 5 average rating, 262 reviews
Guest favourite
Home in Becket
Lake front retreat - Stylish Berkshire home
5 beds
26 Apr – 1 May
4.93 out of 5 average rating, 118 reviews
Superhost
Home in Becket
Tranquil 3-BR Waterfront Retreat
4 beds
23–28 Apr
4.89 out of 5 average rating, 44 reviews
Guest favourite
Flat in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
1 queen bed
5–10 May
4.93 out of 5 average rating, 255 reviews
Guest favourite
Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
1 queen bed
28 Apr – 3 May
4.95 out of 5 average rating, 182 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
Guest favourite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
3 beds
22–27 Apr
4.9 out of 5 average rating, 202 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
Cottage in Becket
Cozy lakeside cottage
3 beds
9–14 Jun
4.95 out of 5 average rating, 125 reviews
Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
2 beds
19–24 May
4.94 out of 5 average rating, 347 reviews
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
5–10 May
5.0 out of 5 average rating, 226 reviews
Guest favourite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
2 beds
21–26 Apr
5.0 out of 5 average rating, 46 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
5 beds
20–25 Apr
4.88 out of 5 average rating, 189 reviews
Guest favourite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
3 beds
2–7 May
5.0 out of 5 average rating, 65 reviews
Guest favourite
Home in Great Barrington
Newly remodeled home with all the modern amenities
4 beds
29 Apr – 4 May
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cabin in West Stockbridge
Modern Cabin near Tanglewood
5 beds
23–28 Apr
4.98 out of 5 average rating, 46 reviews
Home in West Stockbridge
Wellspring by AvantStay | Indoor Pool + Views
9 beds
25–30 Apr
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Great Barrington
Jaw dropping mountain & lake views
4 beds
5–10 May
4.96 out of 5 average rating, 212 reviews