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Guest favorite
Home in Cheshire
Berkshires Lakefront Retreat by Evergreen Home
8 guests4 bedrooms4 beds2.5 baths
May 6 – 11
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May 6 – 11
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ﺩ.ﺇ11,213 for 5 nights
for 5 nights

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Room in Cheshire
Stay with Laura NiraOrganic dayspa owner,
Private sweet sunny room, tranquil home
May 1 – 6
ﺩ.ﺇ1,227 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Cheshire
The Berkshires Hummingbird House
4 beds
May 1 – 6
ﺩ.ﺇ5,747 for 5 nights
for 5 nights
5.0 out of 5 average rating, 51 reviews
Guest favorite
Cabin in Cheshire
Private Paradise in the Berkshires
1 bed
May 1 – 6
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 4 – 9
ﺩ.ﺇ8,502 for 5 nights
for 5 nights
4.85 out of 5 average rating, 214 reviews
Cabin in New Ashford
Charming 2BR Berkshire Cabin
2 queen beds
May 1 – 6
ﺩ.ﺇ3,577 for 5 nights
for 5 nights
New place to stay
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
Top guest favorite
Home in Adams
Mountain Escape - hike, bike, museums, and more!
5 beds
May 1 – 6
ﺩ.ﺇ5,403 for 5 nights
for 5 nights
4.99 out of 5 average rating, 72 reviews
Top guest favorite
Home in Cheshire
Large Secluded Berkshire Home
5 beds
May 1 – 6
ﺩ.ﺇ8,286 for 5 nights
for 5 nights
4.81 out of 5 average rating, 152 reviews
Top guest favorite
Apartment in Adams
Charming/Rustic Apartment with downtown views
2 beds
May 1 – 6
ﺩ.ﺇ2,669 for 5 nights
for 5 nights
4.99 out of 5 average rating, 70 reviews
Guest favorite
Guest suite in Adams
Quaint Suite in Center of Adams
Free cancellation
May 8 – 13
ﺩ.ﺇ2,582 for 5 nights
for 5 nights
4.86 out of 5 average rating, 95 reviews
Top guest favorite
Home in North Adams
Steps to MoCA private house + SAUNA!
6 beds
Jun 15 – 20
ﺩ.ﺇ3,206 for 5 nights
for 5 nights
4.98 out of 5 average rating, 406 reviews
Top guest favorite
Guesthouse in Cummington
Clark Cottage
Free cancellation
May 18 – 23
ﺩ.ﺇ2,851 for 5 nights
for 5 nights
5.0 out of 5 average rating, 76 reviews
Top guest favorite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
4 beds
May 1 – 6
ﺩ.ﺇ8,545 for 5 nights
for 5 nights
5.0 out of 5 average rating, 113 reviews
Guest favorite
Apartment in Adams
Park Street Penthouse
3 beds
May 5 – 10
ﺩ.ﺇ2,927 for 5 nights
for 5 nights
4.88 out of 5 average rating, 17 reviews
Guest suite in Hancock
Cozy apartment near Jiminy Peak
3 beds
May 1 – 6
ﺩ.ﺇ2,071 for 5 nights
for 5 nights
4.81 out of 5 average rating, 180 reviews
Room in Adams
Stay with YishanHosting for 10 years,
1st flr. Near Mt Greylock & AT.
May 2 – 7
ﺩ.ﺇ1,649 for 5 nights
for 5 nights
4.91 out of 5 average rating, 35 reviews
Top guest favorite
Room in Pittsfield
Stay with Eileen
2-Rm Suite in the Berkshires - private BR and Den
May 2 – 7
ﺩ.ﺇ2,325 for 5 nights
for 5 nights
5.0 out of 5 average rating, 53 reviews
Superhost
Home in Cheshire
Berkshire County modern home + pool
Free cancellation
Jun 1 – 6
ﺩ.ﺇ9,148 for 5 nights
for 5 nights
4.93 out of 5 average rating, 70 reviews