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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 private bathrooms
23–28 Aug
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4.95 out of 5 average rating, 217 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 17 reviews, 2 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.92 out of 5 average rating, 48 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 85 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Flat in Pittsfield
Marie's Place
4.91 out of 5 average rating, 316 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
4.98 out of 5 average rating, 457 reviews, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
10–15 Jul
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 87 reviews, 1 double bed, 1.5 bathrooms
12–17 Jul
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4.84 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Aug
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 314 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Lenox
Cozy Home in Lenox
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Jul
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 105 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5.0 out of 5 average rating, 35 reviews, 5 bedrooms, 4.5 bathrooms
26–31 Jul
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 117 reviews, 3 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Resort in Hancock
Country Inn Suite at Jiminy Peak - No fees added
4.72 out of 5 average rating, 266 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Jul