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Search results showing properties in Pittsfield, Massachusetts, United States of America

Google map showing 500 properties

Premier Host
House · 0.8 mi (1.3 km) to the nearest ski lift

Chic Pittsfield Home With A View!

Sleeps 6 · 3 bedrooms · 1+ bathroom
9.0 out of 10 Wonderful (4 reviews)
Unavailable
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Premier Host
House · 0.4 mi (0.7 km) to the nearest ski lift

Dancing Horse Lodge

Sleeps 6 · 3 bedrooms · 1 bathroom
9.4 out of 10 Exceptional (29 reviews)
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Premier Host
House · 1.5 mi (2.3 km) to the nearest ski lift

Country Living just minutes from Everything! Now offering Seasonal Discounts!

Sleeps 8 · 3 bedrooms · 2 bathrooms
10 out of 10 Exceptional (22 reviews)
Unavailable
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House · 0.7 mi (1.1 km) to Pittsfield center

Enjoy Big City Vibes at City Place in the heart of the Berkshires!

Sleeps 7 · 3 bedrooms · 1+ bathroom
8.0 out of 10 Very good (4 reviews)
Unavailable
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House · 2.5 mi (4 km) to Pittsfield center

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Sleeps 25 · 8 bedrooms · 3 bathrooms
9.8 out of 10 Exceptional (126 reviews)
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House · 2.8 mi (4.5 km) to Pittsfield center

house with view in the berkshires

Sleeps 8 · 3 bedrooms · 2 bathrooms
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House · 3 mi (4.9 km) to Pittsfield center

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Sleeps 10 · 4 bedrooms · 4 bathrooms
10 out of 10 Exceptional (46 reviews)
Unavailable
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House · 1.3 mi (2.1 km) to Pittsfield center

Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!

Sleeps 5 · 2 bedrooms · 1 bathroom
10 out of 10 Exceptional (2 reviews)
Unavailable
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House · 3 mi (4.8 km) to Pittsfield center

Lakeside Home With Pool-Completely Renovated

Sleeps 16 · 6 bedrooms · 4+ bathrooms
10 out of 10 Exceptional (29 reviews)
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Cottage · 0.9 mi (1.5 km) to the nearest ski lift

Cozy Berkshire cottage with fireplace.

Sleeps 5 · 3 bedrooms · 1+ bathroom
10 out of 10 Exceptional (20 reviews)
Unavailable
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