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Cheshire
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Over 1,000 places in Cheshire
Guest favorite
Guest favorite
Home in Cheshire
The Berkshires Hummingbird House
4 beds
4 beds
Apr 28 – May 3
Apr 28 – May 3
$250
night
$250 per night
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Guest favorite
Guest favorite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$449
night
$449 per night
4.92 out of 5 average rating, 24 reviews
4.92 (24)
Guest favorite
Guest favorite
Home in Cheshire
Berkshire County modern home + pool
5 beds
5 beds
May 3 – 8
May 3 – 8
$350
night
$350 per night
4.94 out of 5 average rating, 50 reviews
4.94 (50)
Guest favorite
Guest favorite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bed
1 bed
May 28 – Jun 2
May 28 – Jun 2
$155
night
$155 per night
4.89 out of 5 average rating, 152 reviews
4.89 (152)
Guest favorite
Guest favorite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$355
night
$355 per night
5.0 out of 5 average rating, 88 reviews
5.0 (88)
Guest favorite
Guest favorite
Home in Cheshire
Large Secluded Berkshire Home
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$326
$235
night
$235 per night, originally $326
4.8 out of 5 average rating, 144 reviews
4.8 (144)
Guest favorite
Guest favorite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$72
night
$72 per night
4.83 out of 5 average rating, 154 reviews
4.83 (154)
Guest favorite
Guest favorite
Home in Lanesborough
Elmwood Farmhouse
6 beds
6 beds
Apr 27 – May 2
Apr 27 – May 2
$240
night
$240 per night
4.9 out of 5 average rating, 98 reviews
4.9 (98)
Guest favorite
Guest favorite
137
Reviews
4.96
Rating
5
Years hosting
Room in Dalton
Stay with Mary
Stay with Mary
Hosting for 5 years
,
·
Hosting for 5 years
Mother in Law unit in Dalton
Apr 21 – 26
Apr 21 – 26
$65
night
$65 per night
4.96 out of 5 average rating, 137 reviews
4.96 (137)
Guest favorite
Guest favorite
Home in Cheshire
19th c. Barn in The Berkshires
6 beds
6 beds
Apr 20 – 25
Apr 20 – 25
$375
night
$375 per night
4.86 out of 5 average rating, 198 reviews
4.86 (198)
Guest favorite
Guest favorite
Home in Cheshire
Berkshire County Post-and-Beam Barn!
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$500
night
$500 per night
4.97 out of 5 average rating, 62 reviews
4.97 (62)
Guest favorite
Guest favorite
Home in Lanesborough
Scenic mountain getaway.
4 beds
4 beds
Apr 22 – 27
Apr 22 – 27
$250
night
$250 per night
5.0 out of 5 average rating, 47 reviews
5.0 (47)
Guest favorite
Guest favorite
Cottage in Lanesborough
Stone School Cottage
4 beds
4 beds
Apr 20 – 25
Apr 20 – 25
$160
night
$160 per night
4.93 out of 5 average rating, 220 reviews
4.93 (220)
Superhost
Superhost
Cottage in Lanesborough
Wildlife Lakeside Cottage
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$195
night
$195 per night
4.85 out of 5 average rating, 249 reviews
4.85 (249)
Guest favorite
Guest favorite
Home in Adams
Mountain View Hideaway
3 beds
3 beds
Jun 22 – 27
Jun 22 – 27
$120
night
$120 per night
4.91 out of 5 average rating, 68 reviews
4.91 (68)
Guest favorite
Guest favorite
Home in Lanesborough
The Pond House
4 beds
4 beds
May 10 – 15
May 10 – 15
$219
night
$219 per night
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Superhost
Superhost
Home in Dalton
Brooksong, the perfect Berkshires getaway
7 beds
7 beds
Apr 25 – 30
Apr 25 – 30
$370
night
$370 per night
4.92 out of 5 average rating, 170 reviews
4.92 (170)
Guest favorite
Guest favorite
Home in Lanesborough
Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres
10 beds
10 beds
Apr 30 – May 5
Apr 30 – May 5
$852
$741
night
$741 per night, originally $852
4.95 out of 5 average rating, 88 reviews
4.95 (88)
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