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Search results; Over 1,000 homes in Pittsfield

Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 private bathrooms
19–24 Sept
,
4.97 out of 5 average rating, 154 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
4.83 out of 5 average rating, 24 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, 52 reviews, 1 bed, 2 bathrooms
23–28 Aug
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
4.8 out of 5 average rating, 35 reviews, 1 bed, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
4.68 out of 5 average rating, 37 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
4.95 out of 5 average rating, 222 reviews, 3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Guest favourite
Room in Pittsfield
Sunny Room in Downtown Victorian
4.79 out of 5 average rating, 19 reviews, 1 bed, 2 bathrooms
6–11 Aug
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Aug
Guest favourite
Flat in Pittsfield
Marie's Place
4.92 out of 5 average rating, 320 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
4.97 out of 5 average rating, 120 reviews, 3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
5.0 out of 5 average rating, 87 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Guest favourite
Cottage in Lanesborough
Lakefront Cottage w/ Dock & Kayaks
4.88 out of 5 average rating, 8 reviews, 2 bedrooms, 6 beds, 1 bathroom
8–13 Sept
Guest favourite
Cottage in Lanesborough
Wildlife Lakeside Cottage; views/wildlife
4.85 out of 5 average rating, 296 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
Home in New Lebanon
Berkshire Summer Retreat | Minutes to Tanglewood
4.76 out of 5 average rating, 17 reviews, 4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
4.97 out of 5 average rating, 68 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
4.95 out of 5 average rating, 37 reviews, 3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
4.89 out of 5 average rating, 38 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept