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Compare 103 Cottages in Pittsfield with updated reviews, rates, and availability.

Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)

The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)

Family-Friendly Richmond Cottage w/ Private Yard
Family-Friendly Richmond Cottage w/ Private Yard
10.0 out of 10, Exceptional, (4)

Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (107)

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.2 out of 10, Wonderful, (11)

Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (13)

Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (103)

Beachwood Cottage
Beachwood Cottage
10.0 out of 10, Exceptional, (3)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Pittsfield

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,200
AED 4,034 total
includes taxes & fees
11 Apr - 12 Apr

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (139)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
10.0 out of 10, Exceptional, (56)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Life House Berkshires
5/5 Excellent
"Cool vibe. Nice rooms and bedding. Would return!"
A verified traveler stayed at Life House Berkshires
Posted 4 days ago
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