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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
23–28 Aug
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4.95 out of 5 average rating, 216 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds
8–13 Jul
5.0 out of 5 average rating, 41 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds
8–13 Jul
5.0 out of 5 average rating, 4 reviews
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds
26–31 Jul
4.76 out of 5 average rating, 33 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Flat in Pittsfield
Petite Paris
3 bedrooms, 3 beds
7–13 Jul
4.81 out of 5 average rating, 37 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
23–28 Aug
4.92 out of 5 average rating, 48 reviews
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds
30 Aug – 4 Sept
4.95 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds
12–17 Jul
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds
23–28 Aug
4.98 out of 5 average rating, 457 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds
9–14 Aug
4.91 out of 5 average rating, 316 reviews
Top guest favourite
Home in Pittsfield
Marie’s Place unit 3
3 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 64 reviews
Room in Pittsfield
The Yellow Room
1 double bed
27 Jul – 1 Aug
4.84 out of 5 average rating, 87 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed
24–29 Aug
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds
9–14 Jul
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds
28 Jul – 2 Aug
4.93 out of 5 average rating, 104 reviews