
House holiday rentals in Pittsfield
Find and book unique houses on Airbnb
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

Stunning luxury home with pool

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

Hollywood Bungalow in the Berkshires #C0191633410

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

Modern, Renovated Lakefront Escape

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

Solomon Ely Homestead set in walkable downtown

Whispering Woods Guest House

Berkshire Lakehouse - 3 bedrooms - sleeps 5

Getaway w/ Game Room & Theatre

Lakefront Home on Ponstoosuc Lake, The Berkshires

Historic Stone Church in The Berkshires
Private house rentals

Nerd Preservation Sanctuary

Spacious & Family-Ready Home w/ Fenced Yard in Lee

Contemporary Berkshires Home-5 Mins to Jiminy Peak

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

The Red House

Berkshires Black Abbey

Crossings Cottage
Quick stats about house rentals in Pittsfield
Total rentals
90 properties
Nightly prices starting at
$45 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
- Mount Pocono Holiday rentals
- South Jersey Holiday rentals
- The Hamptons Holiday rentals
- Pet-friendly rentals Pittsfield
- Rentals with lake access Pittsfield
- Rentals with pools Pittsfield
- Rentals with a hot tub Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with outdoor seating Pittsfield
- Rentals with a washing machine and dryer Pittsfield
- Waterfront rentals Pittsfield
- Rentals with a patio Pittsfield
- Rentals with a fireplace Pittsfield
- Family-friendly rentals Pittsfield
- Fitness-friendly rentals Pittsfield
- Apartment rentals 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
- 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
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Berkshire Botanical Garden