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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
26–31 Jul
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4.95 out of 5 average rating, 218 reviews
Top guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
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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, 41 reviews
Guest favourite
Home in Pittsfield
A Ray of Sunshine-Lakefront-New Construction- ski
5 bedrooms, 4.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Pittsfield
Spacious 4 Br+ house in the heart of Berkshires
5 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 75 reviews
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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, 85 reviews
Guest favourite
Home in Pittsfield
The Guest House at Cottage Farm
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
4.94 out of 5 average rating, 35 reviews
Guest favourite
Home in Pittsfield
Hidden Oasis in the Mountains by Evergreen Home
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 152 reviews
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Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.93 out of 5 average rating, 105 reviews
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Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 4 reviews
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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, 457 reviews
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Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
6 bedrooms, 10 beds, 4.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 81 reviews
Guest favourite
Home in Lanesborough
Lake, Berkshire Fave, Hot Tub, Lg Open LR, Family
4 bedrooms, 10 beds, 2 bathrooms
24–29 Aug
4.99 out of 5 average rating, 72 reviews
Home in Pittsfield
Four Seasons Retreat
3 bedrooms, 6 beds, 2 bathrooms
27 Jul – 1 Aug
4.76 out of 5 average rating, 33 reviews
Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
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, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 64 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, 48 reviews