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Condo in Hancock
Berkshires Resort with Pools - Lg 1BD - Sleeps 4
4 guests1 bedroom2 beds1 bath
Jun 20 – 25
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Jun 20 – 25
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R18,413 ZAR for 5 nights
for 5 nights

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Top guest favorite
Guesthouse in Pittsfield
The Nest at Birdland
4 beds
Jun 12 – 17
R20,559 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 78 reviews
Top guest favorite
Room in Pittsfield
Stay with CarolynHosting for 5 years,
Equestrian retreat
Jun 15 – 20
R11,573 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 176 reviews
Superhost
Home in Pittsfield
Mid-Century At Friendly Hills
4 beds
Jun 18 – 23
R36,236 ZAR for 5 nights
for 5 nights
New place to stay
Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Free cancellation
Aug 3 – 8
R19,317 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 216 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Jun 22 – 27
R13,278 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 259 reviews
Guest favorite
Apartment in Pittsfield
Green 2 bedroom Downtown
3 beds
Jun 12 – 17
R13,888 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 21 reviews
Room in Pittsfield
Stay with Julia
Spacious Room - North Street (Shared Bathroom)
Jun 11 – 16
R5,261 ZAR for 5 nights
for 5 nights
Top guest favorite
Room in Pittsfield
Stay with LynetteHigher education, pr,
Airy Queen Bedroom with Couch, Pittsfield
Jun 12 – 17
R14,694 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 66 reviews
Top guest favorite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
3 beds
Jun 15 – 20
R9,322 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 18 reviews
Home in Pittsfield
Ohana House
Free cancellation
Jul 5 – 10
R23,148 ZAR for 5 nights
for 5 nights
4.67 out of 5 average rating, 3 reviews
Guest favorite
Guest suite in Richmond
Berkshire Mountain Retreat
2 beds
Jun 11 – 16
R18,517 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 36 reviews
Guesthouse in Canaan
New-Modern! Berkshire Valley guesthouse and pool.
Free cancellation
Sep 9 – 14
R23,337 ZAR for 5 nights
for 5 nights
Guest favorite
Room in Cheshire
Stay with Laura NiraOrganic dayspa owner,
Private sweet sunny room, tranquil home
Jun 18 – 23
R6,650 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Pittsfield
The Guest House at Cottage Farm
4 beds
Jun 11 – 16
R33,269 ZAR for 5 nights
for 5 nights
4.92 out of 5 average rating, 24 reviews
Home in Richmond
Idyllic Berkshires Farmhouse
Free cancellation
Sep 3 – 8
R15,446 ZAR for 5 nights
for 5 nights
4.74 out of 5 average rating, 19 reviews
Top guest favorite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
5 beds
Jun 22 – 27
R23,357 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 64 reviews
Home in Pittsfield
The Fox Hollow Estate
6 beds
Jun 18 – 23
R126,258 ZAR for 5 nights
for 5 nights
Top guest favorite
Home in Pittsfield
Cozy Cottage on Peaceful Pond, Close to Winery
Free cancellation
Aug 9 – 14
R40,970 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 39 reviews