
Holiday houses in Pittsfield
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Top-rated holiday rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Pittsfield holiday rentals
Other great holiday rentals in Pittsfield
Top Guest favourite

Private room in North Chatham
4.93 out of 5 average rating, 361 reviewsArnold Farmhouse (Italianate - private bath)
Guest favourite

Private room in Williamstown
4.87 out of 5 average rating, 628 reviewsRobin's

Apartment in Pittsfield
4.86 out of 5 average rating, 35 reviewsGreen 2 bedroom Downtown

Guest suite in Hancock
4.81 out of 5 average rating, 187 reviewsCozy apartment near Jiminy Peak
Top Guest favourite

Home in Pittsfield
5 out of 5 average rating, 10 reviewsBerkshire Estate
Top Guest favourite

Apartment in Lanesborough
4.9 out of 5 average rating, 135 reviewsCozy Rustic Apt. in 18th c. Berkshire Farmhouse

Apartment in Pittsfield
4.86 out of 5 average rating, 7 reviewsSunny 1 Bedroom Apartment
Guest favourite

Cottage in Pittsfield
5 out of 5 average rating, 6 reviewsCharming Lakeview Cottage in the Berkshires
Quick stats about holiday rentals in Pittsfield
Total rentals
220 properties
Nightly prices starting at
$15 AUD 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
80 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Plainview Holiday rentals
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- Mount Pocono Holiday rentals
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- The Hamptons Holiday rentals
- Waterfront rentals Pittsfield
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- Apartment rentals Pittsfield
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- House rentals Pittsfield
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- Rentals with a washing machine and dryer Pittsfield
- Fitness-friendly rentals Pittsfield
- Pet-friendly rentals Pittsfield
- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Wintonbury Hills Golf Course
- Norman Rockwell Museum
- Taconic State Park
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Stratton Mountain Resort
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Albany Center Gallery
- Bousquet Mountain Ski Area
- Berkshire Botanical Garden