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Guest favorite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
8 guests4 bedrooms4 beds2.5 baths
May 17 – 22
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May 17 – 22
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ﺩ.ﺇ10,999 for 5 nights
for 5 nights

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Guest favorite
Room in Cheshire
Stay with Laura NiraOrganic dayspa owner,
Private sweet sunny room, tranquil home
Jun 1 – 6
ﺩ.ﺇ1,326 for 5 nights
for 5 nights
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Cheshire
The Berkshires Hummingbird House
4 beds
May 18 – 23
ﺩ.ﺇ5,747 for 5 nights
for 5 nights
5.0 out of 5 average rating, 51 reviews
Guest favorite
Cabin in Windsor
Stone cabin in the Berkshires
Free cancellation
Jun 21 – 26
ﺩ.ﺇ4,391 for 5 nights
for 5 nights
4.89 out of 5 average rating, 9 reviews
Guest favorite
Cabin in Cheshire
Private Paradise in the Berkshires
Free cancellation
Jul 6 – 11
ﺩ.ﺇ3,745 for 5 nights
for 5 nights
4.89 out of 5 average rating, 164 reviews
Superhost
Home in Cheshire
19th c. Barn in The Berkshires
6 beds
May 17 – 22
ﺩ.ﺇ8,502 for 5 nights
for 5 nights
4.85 out of 5 average rating, 214 reviews
Top guest favorite
Home in Lanesborough
The Pond House
Free cancellation
May 28 – Jun 2
ﺩ.ﺇ4,658 for 5 nights
for 5 nights
4.94 out of 5 average rating, 36 reviews
Guest favorite
Guest suite in Adams
Quaint Suite in Center of Adams
Free cancellation
May 25 – 30
ﺩ.ﺇ3,056 for 5 nights
for 5 nights
4.86 out of 5 average rating, 95 reviews
Superhost
Home in Cheshire
Berkshire County modern home + pool
5 beds
Jun 1 – 6
ﺩ.ﺇ8,718 for 5 nights
for 5 nights
4.93 out of 5 average rating, 70 reviews
Top guest favorite
Home in North Adams
Steps to MoCA private house + SAUNA!
6 beds
Jun 15 – 20
ﺩ.ﺇ3,122 for 5 nights
for 5 nights
4.98 out of 5 average rating, 413 reviews
Top guest favorite
Guesthouse in Cummington
Clark Cottage
Free cancellation
Jun 22 – 27
ﺩ.ﺇ3,234 for 5 nights
for 5 nights
5.0 out of 5 average rating, 81 reviews
Top guest favorite
Room in Pittsfield
Stay with Eileen
2-Rm Suite in the Berkshires - private BR and Den
May 22 – 27
ﺩ.ﺇ2,325 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Top guest favorite
Home in Savoy
Bear Minimum
Free cancellation
May 23 – 28
ﺩ.ﺇ5,059 for 5 nights
for 5 nights
4.93 out of 5 average rating, 75 reviews
Home in Pittsfield
Pebbled Beach Cottage
Free cancellation
May 26 – 31
ﺩ.ﺇ2,605 for 5 nights
for 5 nights
4.71 out of 5 average rating, 17 reviews
Top guest favorite
Guesthouse in Pittsfield
The Nest at Birdland
Free cancellation
Jun 1 – 6
ﺩ.ﺇ4,198 for 5 nights
for 5 nights
4.96 out of 5 average rating, 77 reviews
Guest favorite
Room in Pittsfield
Stay with Rachel
Charming Turret Room in Downtown Victorian
May 18 – 23
ﺩ.ﺇ1,365 for 5 nights
for 5 nights
4.75 out of 5 average rating, 8 reviews
Top guest favorite
Apartment in Adams
Charming/Rustic Apartment with downtown views
Free cancellation
Jun 3 – 8
ﺩ.ﺇ2,756 for 5 nights
for 5 nights
4.99 out of 5 average rating, 70 reviews
Superhost
Apartment in Adams
full apartment in adams self check in
Free cancellation
May 21 – 26
ﺩ.ﺇ2,583 for 5 nights
for 5 nights
4.85 out of 5 average rating, 133 reviews
Top guest favorite
Guesthouse in Williamstown
Brookside Cottage
Free cancellation
Jun 15 – 20
ﺩ.ﺇ2,234 for 5 nights
for 5 nights
4.96 out of 5 average rating, 180 reviews