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Search results; Over 1,000 homes in Pittsfield

Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
1 bedroom, 2 beds, 1 private bathroom
23–28 Aug
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4.98 out of 5 average rating, 456 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
5.0 out of 5 average rating, 14 reviews, 2 beds, 3 bathrooms
12–17 Jul
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
8–13 Jul
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 215 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.77 out of 5 average rating, 30 reviews, 1 bed, 2 bathrooms
5–10 Jul
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Flat in Pittsfield
Petite Paris
4.81 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
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
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.64 out of 5 average rating, 28 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Home in Pittsfield
Four Seasons Retreat
4.75 out of 5 average rating, 32 reviews, 3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Pittsfield
Berkshire Views
5.0 out of 5 average rating, 19 reviews, 6 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 82 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Room in Pittsfield
The Yellow Room
4.84 out of 5 average rating, 86 reviews, 1 double bed, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
4.93 out of 5 average rating, 104 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.94 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 115 reviews, 3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
4.94 out of 5 average rating, 47 reviews, 1 bed, 2 bathrooms
23–28 Aug
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
4.97 out of 5 average rating, 150 reviews, 5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 63 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Aug