
Holiday houses in Pittsfield
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Top-rated holiday rentals in Pittsfield
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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

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

Home in Pittsfield
5 out of 5 average rating, 8 reviewsBerkshire Estate

Home in Pittsfield
5 out of 5 average rating, 4 reviewsCharming Historic Retreat, <15 min from Lenox
Guest favourite

Farm stay in Adams
5 out of 5 average rating, 13 reviewsBerkshires,pet friendly farm stay w/mountain views
Guest favourite

Apartment in Pittsfield
4.83 out of 5 average rating, 176 reviewsHawksNest: quiet 2BR apt, heart of the Berkshires

Cottage in Pittsfield
5 out of 5 average rating, 5 reviewsCharming Lakeview Cottage in the Berkshires
Guest favourite

Private room in Dalton
4.95 out of 5 average rating, 156 reviewsMother in Law unit in Dalton
Top Guest favourite

Private room in Lee
4.98 out of 5 average rating, 225 reviewsWarm & Welcoming Room w/ Private Bath
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
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a fireplace Pittsfield
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- Rentals with a hot tub Pittsfield
- Rentals with a patio Pittsfield
- Fitness-friendly rentals Pittsfield
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- Rentals with outdoor seating Pittsfield
- Rentals with a washing machine and dryer Pittsfield
- Rentals with pools Pittsfield
- House rentals Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with lake access 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
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Mount Greylock Ski Club
- Taconic State Park
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Sugarloaf State Reservation
- Hancock Shaker Village
- Northern Cross Vineyard
- Opus 40
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Berkshire Botanical Garden