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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, 453 reviews
Guest favourite
Room in Pittsfield
Blue Suite in Downtown Victorian
1 bed, 2 bathrooms
5–10 Jul
4.82 out of 5 average rating, 28 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
New place to stay
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds, 2 bathrooms
6–11 Jul
4.73 out of 5 average rating, 30 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
12–17 Jul
4.93 out of 5 average rating, 43 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
4.95 out of 5 average rating, 213 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 24 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
25–30 Jul
4.84 out of 5 average rating, 85 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
4.92 out of 5 average rating, 311 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 307 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 65 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 10 reviews
Home in Lenox
Walk to Tanglewood from new 2BR Berkshire home!
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Aug
New place to stay
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 103 reviews
Guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 114 reviews
Guest favourite
Home in Lenox
Cozy Home in Lenox
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 7 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, 59 reviews