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
Home in Lee
4.9 out of 5 average rating, 206 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Woodstock
4.91 out of 5 average rating, 643 reviewsDutch Touch Woodstock Cottage
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Home in Putney
4.85 out of 5 average rating, 125 reviewsSpacious Loft with View
Home in Catskill
4.96 out of 5 average rating, 137 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Home in Hudson
4.86 out of 5 average rating, 132 reviews19th Century Mill House with River View
Home in Lenox
4.93 out of 5 average rating, 211 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Home in Woodstock
4.94 out of 5 average rating, 272 reviewsWoodstock Historic Artist Estate - The Pond House
Pet-friendly home rentals with a pool
Tiny home in Brattleboro
4.86 out of 5 average rating, 170 reviews“Sugar Maple” Rustic Cabin Getaway with Fireplace
Cabin in Red Hook
4.96 out of 5 average rating, 308 reviewsModern Upstate Cabin, near Rhinebeck NY
Bungalow in Easthampton
4.92 out of 5 average rating, 436 reviewsThe Creation Station
Tiny home in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
Barn in Hillsdale
4.97 out of 5 average rating, 117 reviewsHudson Valley Hilltop Barn
Cottage in Newfane
4.99 out of 5 average rating, 179 reviewsCozy Vermont Antique Sugar House with Fireplace
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Guesthouse in Stanfordville
4.92 out of 5 average rating, 164 reviewsEco Cottage in the Woods
Private, pet-friendly home rentals
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Farm stay in West Simsbury
4.95 out of 5 average rating, 436 reviewsFlamig Farm Staycation
Cabin in Bennington
4.81 out of 5 average rating, 105 reviewsVermont Cabin - Secluded Woods on South Stream
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 584 reviewsMagic Forest Farm's Mountain View Suite
Tiny home in Jamaica
4.94 out of 5 average rating, 1148 reviewsApple Blossom Cottage: A Tiny House
Loft in Shelburne Falls
4.95 out of 5 average rating, 266 reviewsThe Railroad House
Condo in Hudson
4.94 out of 5 average rating, 144 reviewsHarmony Valley Home, bright & inviting 2-BR escape
Cabin in Tannersville
4.99 out of 5 average rating, 146 reviewsCabin by the woods, Hunter Mountain & Kaaterskills
Quick stats about vacation rentals that are pet-friendly in Pittsfield
Total rentals
70 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
$10 before taxes and fees
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- Pet-friendly rentals Berkshire County
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