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Search results; Over 1,000 places
Over 1,000 places
Boutique hotel in Lenox
Standard King in Boutique Lenox Hotel
1 king bed
1 king bed
Apr 19 – 24
Apr 19 – 24
$98
night
$98 per night
4.62 out of 5 average rating, 262 reviews
4.62 (262)
Guest favorite
Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
1 queen bed
1 queen bed
May 5 – 10
May 5 – 10
$119
$69
night
$69 per night, originally $119
4.93 out of 5 average rating, 255 reviews
4.93 (255)
Guest favorite
Guest favorite
Cottage in Becket
Cozy lakeside cottage
3 beds
3 beds
May 27 – Jun 1
May 27 – Jun 1
$218
$182
night
$182 per night, originally $218
4.95 out of 5 average rating, 124 reviews
4.95 (124)
Guest favorite
Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
3 beds
3 beds
Apr 22 – 27
Apr 22 – 27
$175
$129
night
$129 per night, originally $175
4.9 out of 5 average rating, 202 reviews
4.9 (202)
Superhost
Superhost
Home in Becket
Tranquil 3-BR Waterfront Retreat
4 beds
4 beds
Apr 23 – 28
Apr 23 – 28
$318
$142
night
$142 per night, originally $318
4.89 out of 5 average rating, 44 reviews
4.89 (44)
Guest favorite
Guest favorite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
1 queen bed
1 queen bed
May 6 – 11
May 6 – 11
$130
$111
night
$111 per night, originally $130
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Guest favorite
Guest favorite
Cottage in Becket
BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
2 double beds
2 double beds
Apr 19 – 24
Apr 19 – 24
$179
night
$179 per night
4.94 out of 5 average rating, 237 reviews
4.94 (237)
Guest favorite
Guest favorite
Barn in Great Barrington
Serene Renovated Barn w/ Firepit
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$178
night
$178 per night
5.0 out of 5 average rating, 46 reviews
5.0 (46)
Guest favorite
Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
2 beds
2 beds
May 19 – 24
May 19 – 24
$333
$298
night
$298 per night, originally $333
4.94 out of 5 average rating, 347 reviews
4.94 (347)
Guest favorite
Guest favorite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
2 beds
2 beds
May 5 – 10
May 5 – 10
$297
night
$297 per night
5.0 out of 5 average rating, 225 reviews
5.0 (225)
Guest favorite
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
1 bed
Apr 19 – 24
Apr 19 – 24
$106
night
$106 per night
4.99 out of 5 average rating, 105 reviews
4.99 (105)
Guest favorite
Guest favorite
Home in Becket
Lake front retreat - Stylish Berkshire home
5 beds
5 beds
Apr 26 – May 1
Apr 26 – May 1
$319
$241
night
$241 per night, originally $319
4.93 out of 5 average rating, 118 reviews
4.93 (118)
Guest favorite
Guest favorite
Apartment in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 bed
1 bed
May 5 – 10
May 5 – 10
$154
$103
night
$103 per night, originally $154
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favorite
Guest favorite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$300
$199
night
$199 per night, originally $300
4.88 out of 5 average rating, 189 reviews
4.88 (189)
Guest favorite
Guest favorite
Cottage in Great Barrington
Artist Cottage
1 queen bed
1 queen bed
Apr 29 – May 4
Apr 29 – May 4
$190
night
$190 per night
4.93 out of 5 average rating, 234 reviews
4.93 (234)
Superhost
Superhost
Cabin in Stephentown
Cabin in the woods w cedar Hot Tub + private pond
2 queen beds
2 queen beds
Apr 25 – 30
Apr 25 – 30
$265
$224
night
$224 per night, originally $265
4.84 out of 5 average rating, 236 reviews
4.84 (236)
Guest favorite
Guest favorite
Home in Great Barrington
Granite Ledge, Modern home in a unique setting
3 beds
3 beds
May 2 – 7
May 2 – 7
$362
$242
night
$242 per night, originally $362
5.0 out of 5 average rating, 65 reviews
5.0 (65)
Guest favorite
Guest favorite
Home in Great Barrington
Jaw dropping mountain & lake views
4 beds
4 beds
May 5 – 10
May 5 – 10
$595
night
$595 per night
4.96 out of 5 average rating, 212 reviews
4.96 (212)
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