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, 205 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 30 – Oct 7
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep 19 – 26
Home in Catskill
4.96 out of 5 average rating, 136 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Oct 6 – 13
Home in Germantown
4.95 out of 5 average rating, 363 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Sep 30 – Oct 7
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Feb 20 – 27
Home in Germantown
4.96 out of 5 average rating, 260 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Aug 2 – 9
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Mar 23 – 30
Home in Chatham
4.88 out of 5 average rating, 193 reviewsPet-friendly, Chatham, NY. No neighbors in sight.
Nov 8 – 15
Pet-friendly home rentals with a pool
Tiny home in Brattleboro
4.86 out of 5 average rating, 169 reviews“Sugar Maple” Rustic Cabin Getaway with Fireplace
Dec 8 – 15
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 22 – 29
Farm stay in Saugerties
4.97 out of 5 average rating, 137 reviewsSpring Farm Escape: Animals, Sauna & Mountain View
Oct 18 – 25
Cottage in Newfane
4.99 out of 5 average rating, 178 reviewsCozy Vermont Antique Sugar House with Fireplace
Jan 30 – Feb 6
Tiny home in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
Jul 19 – 26
Farm stay in Red Hook
4.99 out of 5 average rating, 126 reviewsSackett & Van Dam Guest House @ Little 9 Farm 1706
Jul 13 – 20
Farm stay in West Sand Lake
4.98 out of 5 average rating, 139 reviewsRoundhill Farm - Summer Getaway with Pool!
Apr 21 – 28
Cottage in Rhinebeck
4.87 out of 5 average rating, 147 reviewsSecluded peaceful loft in barn by woods
Jan 31 – Feb 7
Private, pet-friendly home rentals
Barn in Marlboro
4.95 out of 5 average rating, 264 reviewsThe Studio With a View. Bring your dog, too!
Mar 24 – 31
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Mar 20 – 27
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Apr 12 – 19
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
Feb 20 – 27
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Feb 12 – 19
Cottage in Becket
4.95 out of 5 average rating, 131 reviewsCozy lakeside cottage
Nov 20 – 27
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
Dec 23 – 30
Apartment in Dummerston
4.96 out of 5 average rating, 163 reviewsHeART Barn Retreat
Sep 4 – 11
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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