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Search results; 218 places in Pittsfield

Resort in Hancock
Club Wyndham Bentley Brook - Two Bedroom Suite
3 beds
20–25 Apr
4.54 out of 5 average rating, 71 reviews
Guest favourite
Apartment in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
1 king bed
21–26 Apr
4.9 out of 5 average rating, 51 reviews
Guest favourite
Flat in Pittsfield
*Berkshire's Sweet Spot 2-Close to Ski Resorts/Spa
5 beds
20–25 Apr
4.85 out of 5 average rating, 60 reviews
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
8 beds
25–30 Apr
4.98 out of 5 average rating, 102 reviews
Superhost
Home in Hancock
Bougie B's Mountainside Getaway
2 beds
25–30 Apr
New place to stay
Guest favourite
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
15 beds
21–26 Apr
4.82 out of 5 average rating, 162 reviews
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
4 beds
24–29 Apr
4.9 out of 5 average rating, 70 reviews
Guest favourite
Home in Lanesborough
Lake Views, Lrg Open Grand Room+Kitchen, Hot Tub
7 beds
20–25 Apr
5.0 out of 5 average rating, 32 reviews
Guest favourite
Tiny home in Chatham
Sugar Shack - 300 square feet of pure sweetness.
1 queen bed
28 Apr – 3 May
4.99 out of 5 average rating, 270 reviews
Guest favourite
Home in Canaan
Private Retreat! Hot Tub, Pool Table & Movie Room
3 beds
31 May – 5 Jun
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Chester
Riverfront Getaway
2 queen beds
29 Apr – 4 May
4.96 out of 5 average rating, 310 reviews
Guest favourite
Apartment in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
7 beds
20–25 Apr
4.93 out of 5 average rating, 58 reviews
Guest favourite
Tiny home in Chatham
HunnyHAUS: Deluxe TINY*private spa*walk to town
2 queen beds
5–10 May
4.99 out of 5 average rating, 307 reviews
Guest favourite
Cottage in Lanesborough
Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak
2 beds
20–25 Apr
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Hancock
Ski-in, Ski-out, Recently Renovated 2BR Condo
2 beds
20–25 Apr
4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Lanesborough
Cozy Berkshire lake house
11–16 May
4.92 out of 5 average rating, 26 reviews
Superhost
Home in Lanesborough
Mountain Blossom Retreat by Evergreen Home
4 beds
27 Apr – 2 May
New place to stay
Guest favourite
Home in Great Barrington
Jaw dropping mountain & lake views
4 beds
5–10 May
4.96 out of 5 average rating, 212 reviews