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Hotel room in Hancock
Skion/Skioff Jiminy Peak Resort
4 guests1 bedroom4 beds1 private bath
Nov 2–7
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Nov 2–7
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$320 CAD per night

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Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bed
Apr 5–10
$238 CAD per night
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Home in Pittsfield
Cozy Cottage on Peaceful Pond, Close to Winery
2 beds
Apr 6–11
$345 CAD per night
4.96 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Pittsfield
Marie's Place
2 queen beds
Apr 6–11
$234 CAD per night
4.91 out of 5 average rating, 255 reviews
Guest favourite
Room in Pittsfield
Stay with CarolynHosting for 5 years,
Equestrian retreat
Apr 1–6
$204 CAD per night
4.96 out of 5 average rating, 175 reviews
Top guest favourite
Guesthouse in Pittsfield
The Nest at Birdland
Free cancellation
Jun 1–6
$361 CAD per night
4.96 out of 5 average rating, 77 reviews
Guest favourite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 beds
Apr 3–8
$143 CAD per night
4.82 out of 5 average rating, 170 reviews
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
6 beds
Apr 14–19
$274 CAD per night
4.87 out of 5 average rating, 289 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
Free cancellation
May 6–11
$269 CAD per night
4.94 out of 5 average rating, 94 reviews
Guest favourite
Farm stay in New Lebanon
1800s Carriage house in Berkshires / Hudson Valley
3 beds
Apr 1–6
$186 CAD per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Pittsfield
The Waffles House-cozy 4br w/hot tub, central loc
5 beds
Apr 1–6
$602 CAD per night
4.93 out of 5 average rating, 15 reviews
Guest favourite
Room in Dalton
Stay with MaryHosting for 6 years,
Mother in Law unit in Dalton
Apr 3–8
$132 CAD per night
4.95 out of 5 average rating, 148 reviews
Top guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 queen bed
Apr 2–7
$219 CAD per night
4.93 out of 5 average rating, 61 reviews
Guest favourite
Home in Lebanon Springs
Stay Near Ski Berkshires + Mid-Week Promo Deals!
4 beds
Apr 6–11
$241 CAD per night
4.9 out of 5 average rating, 40 reviews
Guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 beds
Apr 1–6
$202 CAD per night
4.95 out of 5 average rating, 187 reviews
Bed and breakfast in Pittsfield
Tiny Room & Bath — No Clean Fee!
1 bed
Apr 2–7
$90 CAD per night
4.58 out of 5 average rating, 59 reviews
Guest favourite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
3 beds
Apr 6–11
$398 CAD per night
4.95 out of 5 average rating, 219 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
5 beds
Apr 8–13
$323 CAD per night
4.94 out of 5 average rating, 159 reviews
Top guest favourite
Guesthouse in Stephentown
Dog Friendly Studio
1 queen bed
Apr 1–6
$359 CAD per night
5.0 out of 5 average rating, 406 reviews