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Search results; Over 1,000 homes in Pittsfield

Top guest favorite
Room in Pittsfield
Spacious suite with homemade breakfast included
1 bedroom, 2 beds, 1 private bath
Aug 23 – 28
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4.98 out of 5 average rating, 464 reviews
Top guest favorite
Home in Pittsfield
Pond-front with a fireplace and kayak
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 27 – Sep 1
Hotel room in Pittsfield
Indoor pool and hot tub in Berkshires
4.65 out of 5 average rating, 43 reviews, 1 bedroom, 2 beds, 1 bath
Aug 22 – 27
Guest favorite
Apartment in Pittsfield
Newly renovated, minutes from ski and downtown
4.92 out of 5 average rating, 324 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Guest favorite
Home in Pittsfield
Grand piano and a game room
4.96 out of 5 average rating, 228 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
Top guest favorite
Home in Pittsfield
1847 farmhouse with a wraparound porch
5.0 out of 5 average rating, 43 reviews, 4 bedrooms, 4 beds, 1.5 baths
Sep 8 – 13
Top guest favorite
Home in Pittsfield
Colonial home with a porch and yard
4.97 out of 5 average rating, 71 reviews, 3 bedrooms, 3 beds, 1.5 baths
Aug 23 – 28
Guest favorite
Room in Pittsfield
Themed room in a Queen Anne Victorian
4.86 out of 5 average rating, 28 reviews, 2 beds, 3 baths
Aug 30 – Sep 4
Guest favorite
Apartment in Pittsfield
Renovated 1896 Colonial with a screened porch
4.84 out of 5 average rating, 194 reviews, 2 bedrooms, 2 beds, 1.5 baths
Nov 1 – 6
Guest favorite
Cottage in Lanesborough
Lakeside peninsula cottage with abundant wildlife
4.85 out of 5 average rating, 297 reviews, 3 bedrooms, 4 beds, 2.5 baths
Oct 5 – 10
Top guest favorite
Home in Lee
Wood-fired hot tub near Tanglewood
4.99 out of 5 average rating, 313 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 20 – 25
Guest favorite
Home in Pittsfield
Lake views, a fire pit, and fireplace
4.97 out of 5 average rating, 71 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 2 – 7
Guest favorite
Home in Pittsfield
Restored retreat on 12 private acres
4.95 out of 5 average rating, 38 reviews, 3 bedrooms, 4 beds, 3 baths
Aug 24 – 29
Top guest favorite
Room in Pittsfield
Sunrooms, garden, and fire pit in Berkshires
5.0 out of 5 average rating, 88 reviews, 1 queen bed, 1 bath
Oct 3 – 8
Top guest favorite
Home in Pittsfield
Lakefront with a pool and kayaks
4.98 out of 5 average rating, 82 reviews, 6 bedrooms, 10 beds, 4.5 baths
Oct 4 – 9
Guest favorite
Cottage in Pittsfield
Lake and mountain views on Onota Lake
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bath
Sep 9 – 14
Home in Lenox
1893 cottage on a Gilded Age estate
New place to stay, 2 bedrooms, 2 beds, 1.5 baths
Aug 22 – 27
Top guest favorite
Home in Pittsfield
Newly renovated with cathedral ceilings, near Tanglewood
4.95 out of 5 average rating, 75 reviews, 5 bedrooms, 5 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
Home in New Lebanon
Modernized 1860s home with lake access
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 2.5 baths
Aug 23 – 28