
Pet-friendly holiday 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.
Holiday 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

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Elmwood Farmhouse

Berkshire Lakehouse - 3 bedrooms - sleeps 5

BB's Central Berkshire Home

Cheerful Catskill Village Cottage

19th c. Barn in The Berkshires

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

A private Berkshires retreat with a tennis court!
Pet-friendly home rentals with a pool

Country Getaway Tiny House in woods w/Pool/Sauna

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Cozy cottage with pool, walking distance to lake

Cozy Cottage with Pool

Modern Upstate Cabin, near Rhinebeck NY

Enjoy every season the Berkshires have to offer.

Mt Snow Chalet: Peaceful Escape w/Hot Tub
Private, pet-friendly home rentals

Mid-Century At Friendly Hills w Guest Passes !

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

Quiet Studio in Desirable Neighborhood

Explore the Berkshires from this charming home.

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

Luxury Cabin | Fall Foliage, & Autumn Adventures

Folk Art Studio: 1-bedroom near the Berkshires

Modern Gem in the Heart of Berkshires
Quick stats about holiday rentals that are pet-friendly in Pittsfield
Total rentals
80 properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
3.3K 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
- 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
- Apartment rentals Pittsfield
- 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
- 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
- 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