Pet-friendly holiday 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.
Holiday 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.
18–25 Oct
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
19–26 Oct
Home in Woodstock
4.94 out of 5 average rating, 268 reviewsWoodstock Historic Artist Estate - The Pond House
21–28 Nov
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
26 Mar – 2 Apr
Home in Germantown
4.95 out of 5 average rating, 363 reviewsScandinavian Barn Featured in Airbnb Magazine
20–27 Sept
Home in Woodstock
4.91 out of 5 average rating, 641 reviewsDutch Touch Woodstock Cottage
21–28 Nov
Home in Germantown
4.96 out of 5 average rating, 258 reviewsGermantown Cottage/Catskills Views/H River Trails!
7–14 Sept
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
7–14 Jan
Pet-friendly home rentals with a pool
Tiny home in Brattleboro
4.86 out of 5 average rating, 166 reviews“Sugar Maple” Rustic Cabin Getaway with Fireplace
8–15 Dec
Cabin in Red Hook
4.96 out of 5 average rating, 305 reviewsModern Upstate Cabin, near Rhinebeck NY
25 Sept – 2 Oct
Barn in Hillsdale
4.97 out of 5 average rating, 117 reviewsHudson Valley Hilltop Barn
3–10 Sept
Cottage in Newfane
4.99 out of 5 average rating, 177 reviewsCozy Vermont Antique Sugar House with Fireplace
20–27 Aug
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
21–28 Jul
Farm stay in Saugerties
4.97 out of 5 average rating, 137 reviewsSpring Farm Escape: Animals, Sauna & Mountain View
5–12 Sept
Tiny home in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
29 May – 5 Jun
Cottage in Rhinebeck
4.87 out of 5 average rating, 147 reviewsSecluded peaceful loft in barn by woods
23–30 Apr
Private, pet-friendly home rentals
Cottage in Hillsdale
4.94 out of 5 average rating, 171 reviewsCozy Cottage Catamount, Berkshires Walk to Brewery
9–16 Jan
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
2–7 May
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
6–13 Feb
Loft in Shelburne Falls
4.95 out of 5 average rating, 264 reviewsThe Railroad House
25 Sept – 2 Oct
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
16–23 Mar
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
31 Mar – 7 Apr
Flat in Northampton
4.95 out of 5 average rating, 280 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
18–25 Sept
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
25 Jul – 1 Aug
Quick stats about holiday 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
£8 before taxes and fees
Destinations to explore
- New City Holiday rentals
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- Lake George Holiday rentals
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- Pet-friendly rentals New York
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- Rentals with a firepit Pittsfield
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