
Vacation rentals in Pittsfield
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Top-rated vacation rentals in Pittsfield
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Popular amenities for Pittsfield vacation rentals
Other great vacation rentals in Pittsfield
Guest favourite

Apartment in Pittsfield
4.91 out of 5 average rating, 23 reviewsGreen 2 bedroom Downtown
Superhost

Apartment in Pittsfield
4.83 out of 5 average rating, 30 reviewsPetite Paris
Guest favourite

Home in Lanesborough
5 out of 5 average rating, 10 reviewsLakefront Home on Ponstoosuc Lake, The Berkshires
Guest favourite

Home in Pittsfield
4.95 out of 5 average rating, 79 reviewsBB's Central Berkshire Home
Guest favourite

Home in Lanesborough
4.96 out of 5 average rating, 51 reviewsHistoric Stone Church in The Berkshires
Top guest favourite

Home in Pittsfield
4.98 out of 5 average rating, 60 reviewsSpacious 4 Br+ house in the heart of Berkshires

Home in Pittsfield
4.76 out of 5 average rating, 21 reviewsPebbled Beach Cottage
Guest favourite

Cottage in Great Barrington
4.94 out of 5 average rating, 137 reviewsThe Cottage at The Barrington House
Quick stats about vacation rentals in Pittsfield
Total rentals
230 properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
8.3K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Hudson Valley Vacation rentals
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- Rentals with a patio Pittsfield
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- Rentals with pools Pittsfield
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- Stratton Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Stratton Mountain Resort
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hildene, The Lincoln Family Home
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Clarksburg State Park