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Superhost
Apartment in Hancock
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
8 guests2 bedrooms6 beds1 bath
Jul 30 – Aug 4
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Jul 30 – Aug 4
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R26,783 ZAR for 5 nights

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Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Free cancellation
Aug 17 – 22
R14,161 ZAR for 5 nights
4.99 out of 5 average rating, 233 reviews
Guest favorite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
3 beds
Jul 20 – 25
R9,272 ZAR for 5 nights
4.92 out of 5 average rating, 24 reviews
Top guest favorite
Room in Pittsfield
Stay with CarolynHosting for 6 years,
Equestrian retreat
Aug 10 – 15
R11,590 ZAR for 5 nights
4.96 out of 5 average rating, 180 reviews
Top guest favorite
Home in Pittsfield
Cozy Cottage on Peaceful Pond, Close to Winery
Free cancellation
Sep 1 – 6
R37,298 ZAR for 5 nights
4.98 out of 5 average rating, 41 reviews
Superhost
Home in Pittsfield
Mid-Century At Friendly Hills w Guest Passes !
4 beds
Aug 11 – 16
R33,484 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Pittsfield
South Hancock Estate on 5 acres
6 beds
Jul 19 – 24
R42,145 ZAR for 5 nights
5.0 out of 5 average rating, 3 reviews
Apartment in New Lebanon
Loft Space above Brewery
3 beds
Jul 21 – 26
R17,722 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
Guest favorite
Apartment in New Lebanon
Airy apartment at the old boarding house
Free cancellation
Aug 20 – 25
R14,014 ZAR for 5 nights
4.96 out of 5 average rating, 105 reviews
Guest favorite
Place to stay in Stockbridge
Cozy room w/private bath–near Kripalu/ Tanglewood
Free cancellation
Sep 6 – 11
R12,391 ZAR for 5 nights
4.86 out of 5 average rating, 94 reviews
Home in Pittsfield
Pebbled Beach Cottage
Free cancellation
Aug 11 – 16
R14,856 ZAR for 5 nights
4.77 out of 5 average rating, 22 reviews
Top guest favorite
Guesthouse in Canaan
New-Modern! Berkshire Valley guesthouse and pool.
Free cancellation
Sep 14 – 19
R20,019 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Home in New Lebanon
Mountain View Getaway
Free cancellation
Jul 27 – Aug 1
R38,036 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
Aug 17 – 22
R21,262 ZAR for 5 nights
4.95 out of 5 average rating, 178 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Jul 20 – 25
R16,332 ZAR for 5 nights
4.91 out of 5 average rating, 269 reviews
Guest favorite
Apartment in Lenox
Station House 1E Private Room & Bath
Free cancellation
Aug 20 – 25
R8,429 ZAR for 5 nights
4.88 out of 5 average rating, 191 reviews
Top guest favorite
Room in Pittsfield
Stay with LynetteHigher education, pr,
Pittsfield. Large queen bedroom, second floor.
Jul 30 – Aug 4
R14,715 ZAR for 5 nights
4.95 out of 5 average rating, 44 reviews
Top guest favorite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
Free cancellation
Oct 19 – 24
R25,224 ZAR for 5 nights
5.0 out of 5 average rating, 69 reviews
Home in Valatie
Lakefront Year-round! Kayak, Fish, Swim, Hammock
Free cancellation
Sep 2 – 7
R34,422 ZAR for 5 nights
5.0 out of 5 average rating, 3 reviews