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, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep. 2 – 9
Home in Lenox
4.93 out of 5 average rating, 209 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep. 14 – 21
Home in Germantown
4.95 out of 5 average rating, 362 reviewsScandinavian Barn Featured in Airbnb Magazine
May 28 – Jun. 4
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Nov. 9 – 16
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Jan. 26 – Feb. 2
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Apr. 7 – 14
Home in Germantown
4.96 out of 5 average rating, 256 reviewsGermantown Cottage/Catskills Views/H River Trails!
Aug. 9 – 16
Home in Schenectady
4.98 out of 5 average rating, 168 reviewsBright & Clean ~Tons of Upgrades ~Office Space
Jul. 5 – 12
Pet-friendly home rentals with a pool
Tiny homes in Brattleboro
4.86 out of 5 average rating, 166 reviews“Sugar Maple” Rustic Cabin Getaway with Fireplace
Nov. 13 – 20
Barn in Hillsdale
4.97 out of 5 average rating, 117 reviewsHudson Valley Hilltop Barn
Sep. 23 – 30
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug. 21 – 28
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
Jul. 21 – 26
Cottage in Newfane
4.99 out of 5 average rating, 176 reviewsCozy Vermont Antique Sugar House with Fireplace
Jan. 25 – Feb. 1
Tiny homes in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
May 6 – 13
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Dec. 4 – 11
Cottage in Rhinebeck
4.87 out of 5 average rating, 147 reviewsSecluded peaceful loft in barn by woods
Nov. 1 – 8
Private, pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 250 reviewsWildlife Lakeside Cottage
Feb. 14 – 21
Loft in Shelburne Falls
4.95 out of 5 average rating, 264 reviewsThe Railroad House
Sep. 5 – 12
Cottage in Craryville
4.91 out of 5 average rating, 481 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Oct. 12 – 19
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
May 29 – Jun. 5
Cabin in Bennington
4.8 out of 5 average rating, 102 reviewsVermont Cabin - Secluded Woods on South Stream
Sep. 18 – 25
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
Mar. 29 – Apr. 5
Tiny homes in Cambridge
4.95 out of 5 average rating, 168 reviewsRunamuk Farm camp with a view!
May 30 – Jun. 6
Cottage in Florida
4.82 out of 5 average rating, 101 reviewsPeaceful Mountain Cabin by Ski, Kayak, Museums +!
Nov. 12 – 19
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
$14 CAD before taxes and fees
Destinations to explore
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