
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

Mid-Century At Friendly Hills w Guest Passes !

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Elmwood Farmhouse

Modern Barn on 12 acres w Sauna, FirePit+swimming

BB's Central Berkshire Home

19th c. Barn in The Berkshires

MillSpring House

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

Waterfront Lake Home, close to Hunter & Windham

Country Getaway Tiny House in woods w/Pool/Sauna

The Copake Cabin - A rustic-modern retreat.

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

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

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

Berkshire Lakehouse - 3 bedrooms - sleeps 5

Cabin Nestled in the Pines (New Arcade Machine!)

Berkshires Pet friendly Farm stay, Mountain views

Cozy Winter Chalet I Close to Ski & Downtown Lenox

Luxury Cabin | Fall Foliage, & Autumn Adventures

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

NEW RENO - Chalet-style farm loft near Tanglewood
Quick stats about vacation rentals that are pet-friendly in Pittsfield
Total rentals
80 properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
3.5K 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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- Waterfront rentals Pittsfield
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- Pet-friendly rentals Berkshire County
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- 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