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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 beds, 1 shared bathroom
9–14 Aug
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4.92 out of 5 average rating, 320 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.83 out of 5 average rating, 24 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 221 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 52 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.68 out of 5 average rating, 37 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 120 reviews
Guest favourite
Flat in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Nov
4.84 out of 5 average rating, 194 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 319 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 66 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
26–31 Aug
4.84 out of 5 average rating, 88 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
4.95 out of 5 average rating, 37 reviews
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
4.89 out of 5 average rating, 37 reviews
Flat in Pittsfield
Spacious Green 2 bedroom Downtown
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 51 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Home in New Lebanon
Berkshire Summer Retreat | Minutes to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.76 out of 5 average rating, 17 reviews