filters

Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
,
4.99 out of 5 average rating, 314 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 17 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 4 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, 25 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 216 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, 48 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
4.91 out of 5 average rating, 316 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 456 reviews
Home in Lanesborough
Casa Demeo, Private Berkshire Retreat
3 bedrooms, 3 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
5.0 out of 5 average rating, 12 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, 83 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 49 reviews
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds, 1 bathroom
6–11 Jul
4.91 out of 5 average rating, 66 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
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Aug
4.97 out of 5 average rating, 63 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Nov
4.97 out of 5 average rating, 67 reviews
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
4.76 out of 5 average rating, 33 reviews