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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
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4.97 out of 5 average rating, 154 reviews
Top guest favourite
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, 30 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.83 out of 5 average rating, 24 reviews
Hotel room in Pittsfield
1 BD • Berkshires Apartment • Full Kitchen/Pool
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.68 out of 5 average rating, 37 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, 52 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.95 out of 5 average rating, 222 reviews
Guest favourite
Flat in Pittsfield
Marie's Place
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 320 reviews
Top guest favourite
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, 87 reviews
Top guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Pittsfield
Marie's Place, Unit 1
3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 120 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, 68 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 42 reviews
Home in New Lebanon
Spacious 4BR Summer Escape | Queechy Lake Passes
4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.76 out of 5 average rating, 17 reviews
Room in Pittsfield
The Yellow Room
1 double bed, 1.5 bathrooms
29 Aug – 3 Sept
4.84 out of 5 average rating, 89 reviews
Guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 109 reviews
Top guest favourite
Home in Lanesborough
The Pond House
3 bedrooms, 4 beds, 1 bathroom
20–25 Nov
4.96 out of 5 average rating, 52 reviews
Guest favourite
Townhouse in Hancock
Jiminy Peak Slopeside Getaway • Ski & Adventure
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 12 reviews
Home in Lanesborough
New built - Split level house in the Berkshires
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 3 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