
Pet-friendly vacation rentals in Pittsfield
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Pittsfield
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Pittsfield pet-friendly home rentals
Pet-friendly house rentals

Escape to Lakefront Leisure—Amazing views!

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Elmwood Farmhouse

Private Cottage/Mountain Views/Trails/Fire pit

Modern Barn on 12 acres w Sauna, FirePit+swimming

19th c. Barn in The Berkshires

Rustic Swedish Barn/Featured in Airbnb Magazine

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Pet-friendly home rentals with a pool

Country Getaway Tiny House in woods w/Pool/Sauna

The Copake Cabin - A rustic-modern retreat.

Cozy cottage with pool, walking distance to lake

Cozy Cottage with Pool

Eco Cottage in the Woods

Modern Upstate Cabin, near Rhinebeck NY

Enjoy every season the Berkshires have to offer.

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm
Private, pet-friendly home rentals

Mid-Century At Friendly Hills w Guest Passes !

Berkshire Lakehouse - 3 bedrooms - sleeps 5

Columbia County Getaway - Raspberry Ridge Cottage

BB's Central Berkshire Home

MillSpring House

Luxury Cabin | Fall Foliage, & Autumn Adventures

Cottage on Scenic Road

1800s Carriage house in Berkshires / Hudson Valley
Quick stats about vacation rentals that are pet-friendly in Pittsfield
Total rentals
70 properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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- House rentals Pittsfield
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- Pet-friendly rentals Berkshire County
- Pet-friendly rentals Massachusetts
- Pet-friendly 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
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Albany Center Gallery
- Talcott Mountain State Park