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.
Oct 18 – 25
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
May 9 – 16
Home in Woodstock
4.91 out of 5 average rating, 641 reviewsDutch Touch Woodstock Cottage
Nov 8 – 15
Home in Woodstock
4.94 out of 5 average rating, 268 reviewsWoodstock Historic Artist Estate - The Pond House
Nov 5 – 12
Home in Germantown
4.95 out of 5 average rating, 363 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Oct 16 – 23
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Mar 5 – 12
Home in Germantown
4.96 out of 5 average rating, 258 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Jul 19 – 26
Home in Schenectady
4.98 out of 5 average rating, 168 reviewsBright & Clean ~Tons of Upgrades ~Office Space
Jun 17 – 24
Pet-friendly home rentals with a pool
Tiny home in Brattleboro
4.86 out of 5 average rating, 167 reviews“Sugar Maple” Rustic Cabin Getaway with Fireplace
Dec 5 – 12
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 23 – 30
Cottage in Newfane
4.99 out of 5 average rating, 177 reviewsCozy Vermont Antique Sugar House with Fireplace
Apr 4 – 11
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
Jul 21 – 28
Farm stay in Saugerties
4.97 out of 5 average rating, 137 reviewsSpring Farm Escape: Animals, Sauna & Mountain View
Oct 2 – 9
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Dec 8 – 15
Tiny home in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
Jul 8 – 15
Farm stay in Red Hook
4.99 out of 5 average rating, 126 reviewsSackett & Van Dam Guest House @ Little 9 Farm 1706
Dec 2 – 9
Private, pet-friendly home rentals
Loft in Shelburne Falls
4.95 out of 5 average rating, 265 reviewsThe Railroad House
Mar 21 – 28
Apartment in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Mar 8 – 15
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Feb 9 – 16
Cottage in Becket
4.95 out of 5 average rating, 130 reviewsCozy lakeside cottage
Jan 5 – 12
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Nov 1 – 8
Guesthouse in Germantown
4.96 out of 5 average rating, 188 reviewsLuxe Guest House Retreat
Oct 22 – 29
Farm stay in Coeymans Hollow
4.85 out of 5 average rating, 579 reviewsMagic Forest Farm's Mountain View Suite
Oct 2 – 9
Cabin in Catskill
4.92 out of 5 average rating, 456 reviewsGetaway Eastern Catskills - Catskills East
Mar 16 – 23
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
G$2,090 GYD before taxes and fees
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