
House holiday rentals in Pittsfield
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Top-rated house rentals in Pittsfield
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield house rentals
House rentals with a pool

Private lakefront home, hot tub & resort amenities

Adams Farm-"The Little Farmhouse"

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Stylish Rural Sanctuary! (+ Summer Pool)

Hollywood Bungalow in the Berkshires #C0191633410

Casa Luna Country Retreat with Pool, Hudson, NY
Weekly house rentals

The Waffles House-cozy 4br w/hot tub, sleeps 8

Whispering Woods Guest House

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Historic Stone Church in The Berkshires

Airy Upstate Getaway with a View

Guest Fave, 15 Min Jiminy, Large Open LR, Hot Tub

Charming lake home with amazing sunset views

The Berkshires Hummingbird House
Private house rentals

Stunning Fall Views! Hot Tub/Movie Room/Game Room

Cozy. Clean. Free bagel shop.

Contemporary Berkshires Home-5 Mins to Jiminy Peak

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Newly Renovated Lakefront Haven In Lenox

The Red House

South Hancock Estate on 5 acres

Berkshires Black Abbey
Quick stats about house rentals in Pittsfield
Total rentals
90 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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
- Waterfront rentals Pittsfield
- Rentals with a hot tub Pittsfield
- Rentals with a patio Pittsfield
- Fitness-friendly rentals Pittsfield
- Family-friendly rentals Pittsfield
- Pet-friendly rentals Pittsfield
- Apartment rentals Pittsfield
- Rentals with outdoor seating Pittsfield
- Rentals with a washing machine and dryer Pittsfield
- Rentals with pools Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with lake access Pittsfield
- House rentals Berkshire County
- House rentals Massachusetts
- House rentals United States
- 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