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Condo in Hancock
Condo Resort at Jiminy Peak Ski Mountain's Base
8 guests2 bedrooms4 beds2 baths
Apr 17 – 22
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Apr 17 – 22
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$3,531 for 5 nights
for 5 nights

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Top guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr 13 – 18
$708 for 5 nights
for 5 nights
4.99 out of 5 average rating, 199 reviews
Top guest favorite
Guesthouse in Pittsfield
The Nest at Birdland
Free cancellation
Jun 1 – 6
$1,124 for 5 nights
for 5 nights
4.96 out of 5 average rating, 77 reviews
Top guest favorite
Home in Pittsfield
Cozy Cottage on Peaceful Pond, Close to Winery
2 beds
Apr 27 – May 2
$1,323 for 5 nights
for 5 nights
4.96 out of 5 average rating, 27 reviews
Guest favorite
Room in Pittsfield
Stay with CarolynHosting for 5 years,
Equestrian retreat
Apr 13 – 18
$628 for 5 nights
for 5 nights
4.96 out of 5 average rating, 175 reviews
Guest favorite
Home in Pittsfield
Dancing Horse Lodge
6 beds
Apr 23 – 28
$850 for 5 nights
for 5 nights
4.87 out of 5 average rating, 290 reviews
Guest favorite
Apartment in Pittsfield
Marie's Place
2 queen beds
Apr 20 – 25
$720 for 5 nights
for 5 nights
4.91 out of 5 average rating, 255 reviews
Guest favorite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
Free cancellation
May 6 – 11
$843 for 5 nights
for 5 nights
4.93 out of 5 average rating, 96 reviews
Guest favorite
Farm stay in New Lebanon
NEW RENO - Historic Loft w/views of the Berkshires
3 beds
Apr 13 – 18
$525 for 5 nights
for 5 nights
4.94 out of 5 average rating, 16 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Free cancellation
Apr 29 – May 4
$468 for 5 nights
for 5 nights
4.82 out of 5 average rating, 171 reviews
Top guest favorite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
5 beds
Apr 20 – 25
$1,267 for 5 nights
for 5 nights
5.0 out of 5 average rating, 57 reviews
Top guest favorite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
3 beds
Apr 13 – 18
$502 for 5 nights
for 5 nights
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
Apr 18 – 23
$993 for 5 nights
for 5 nights
4.94 out of 5 average rating, 161 reviews
Guest favorite
Home in Lebanon Springs
Spring Getaway Near Berkshires + Midweek Deals!
4 beds
Apr 11 – 16
$897 for 5 nights
for 5 nights
4.9 out of 5 average rating, 40 reviews
Home in Pittsfield
Spacious Farmhouse with Stunning Views
Free cancellation
Apr 14 – 19
$1,769 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
Free cancellation
Apr 24 – 29
$536 for 5 nights
for 5 nights
4.93 out of 5 average rating, 61 reviews
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
Apr 19 – 24
$1,324 for 5 nights
for 5 nights
4.95 out of 5 average rating, 220 reviews
Guest favorite
Home in Pittsfield
The Waffles House-cozy 4br w/hot tub, central loc
5 beds
Apr 15 – 20
$1,854 for 5 nights
for 5 nights
4.93 out of 5 average rating, 15 reviews
Guest favorite
Room in Dalton
Stay with MaryHosting for 6 years,
Mother in Law unit in Dalton
Apr 12 – 17
$405 for 5 nights
for 5 nights
4.95 out of 5 average rating, 149 reviews