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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
9–14 Aug
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4.95 out of 5 average rating, 221 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
26–31 Jul
4.83 out of 5 average rating, 24 reviews
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
1 bed, 2 bathrooms
21–26 Jul
4.79 out of 5 average rating, 19 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, 51 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
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
26–31 Aug
4.84 out of 5 average rating, 88 reviews
Top guest favourite
Room in Pittsfield
Creative Haven in the Berkshires - Nest Room
1 queen bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
23–28 Aug
4.8 out of 5 average rating, 35 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, 317 reviews
Guest favourite
Guest suite in Pittsfield
Newly Renovated Red Door Annex
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 128 reviews
Top guest favourite
Room in Pittsfield
Airy Queen Bedroom with Couch, Pittsfield
1 queen bed, 1 bathroom
26–31 Jul
4.96 out of 5 average rating, 72 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, 462 reviews
Room in Pittsfield
Cozy room in Pittsfield #2
1 double bed, 1.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 320 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
24–29 Aug
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Pittsfield
Comfy Quaint Tavern
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 70 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 120 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 133 reviews