
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

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Stunning luxury home with pool

Modern Barn on 12 acres w Sauna, FirePit+swimming

Stylish Rural Sanctuary + Heated Pool (Seasonal)!

Hollywood Bungalow in the Berkshires #C0191633410

Hilltop modern with stunning mountain views

Casa Luna Country Retreat with Pool, Hudson, NY

Berkshire Getaway Ranch 3 acres + saltwater pool
Weekly house rentals

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

Solomon Ely Homestead set in walkable downtown

Whispering Woods Guest House

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Spacious Farmhouse with Stunning Views

BB's Central Berkshire Home

South Hancock Estate on 5 acres

Spacious 4 Br+ house in the heart of Berkshires
Private house rentals

Private Retreat: Hot Tub! Movie Room! Pool Table!

Contemporary Berkshires Home-5 Mins to Jiminy Peak

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

New Shaw Pond Skytop Retreat in the Berkshires

The Red House

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

Berkshires Black Abbey

Guest Fave, 15 Min Jiminy, Large Open LR, Hot Tub
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
- Hudson Valley Holiday rentals
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- The Hamptons Holiday rentals
- Plainview Holiday rentals
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- Philadelphia Holiday rentals
- Montreal Holiday rentals
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- Rentals with a hot tub Pittsfield
- Rentals with pools Pittsfield
- Apartment rentals Pittsfield
- Kid-friendly rentals Pittsfield
- Rentals with a patio Pittsfield
- Rentals with a fireplace Pittsfield
- Rentals with lake access Pittsfield
- Fitness-friendly rentals Pittsfield
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- Rentals with a washing machine and dryer Pittsfield
- Family-friendly rentals Pittsfield
- Waterfront rentals Pittsfield
- Rentals with a fire pit Pittsfield
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- Stratton Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Zoom Flume
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Beartown State Forest
- Talcott Mountain State Park
- Wintonbury Hills Golf Course
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Bright Nights at Forest Park
- Hancock Shaker Village