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, 205 reviews1817 Berkshire Farmhouse- Close to Everything.
3–10 Oct
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
3–10 Oct
Home in Woodstock
4.94 out of 5 average rating, 271 reviewsWoodstock Historic Artist Estate - The Pond House
10–17 Dec
Home in Woodstock
4.91 out of 5 average rating, 641 reviewsDutch Touch Woodstock Cottage
15–22 Feb
Home in Pittsfield
4.82 out of 5 average rating, 164 reviewsBeautiful House By The Lake W/Jetted Hot Tub
26 Jan – 2 Feb
Home in Germantown
4.96 out of 5 average rating, 260 reviewsModern Cottage, Views, Walking Trails, Fireplace!
15–22 Jun
Home in Germantown
4.95 out of 5 average rating, 363 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
28 May – 4 Jun
Home in Catskill
4.96 out of 5 average rating, 136 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
2–9 Jan
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
27 May – 3 Jun
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
22–29 Aug
Tiny home in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
10–17 Jun
Cottage in Newfane
4.99 out of 5 average rating, 178 reviewsCozy Vermont Antique Sugar House with Fireplace
3–10 Sep
Farm stay in Saugerties
4.97 out of 5 average rating, 137 reviewsSpring Farm Escape: Animals, Sauna & Mountain View
10–17 Sep
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
19–26 Jul
Farm stay in West Sand Lake
4.98 out of 5 average rating, 139 reviewsRoundhill Farm - Summer Getaway with Pool!
20–27 Oct
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
10–17 Nov
Private, pet-friendly home rentals
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
31 Mar – 7 Apr
Barn in Marlboro
4.95 out of 5 average rating, 264 reviewsThe Studio With a View. Bring your dog, too!
9–16 Jan
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
13–20 Feb
Tiny home in Jamaica
4.94 out of 5 average rating, 1146 reviewsApple Blossom Cottage: A Tiny House
4–11 Apr
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
25 Apr – 2 May
Flat in Sheffield
4.92 out of 5 average rating, 123 reviewsPrivate Berkshire Barn Apartment
15–22 May
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
4–11 Sep
Cottage in Florida
4.82 out of 5 average rating, 102 reviewsPeaceful Mountain Cabin by Ski, Kayak, Museums +!
7–14 Apr
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
€ 9 before taxes and fees
Destinations to explore
- New City Holiday rentals
- New Haven Holiday rentals
- Lake George Holiday rentals
- Catskill Holiday rentals
- Albany Holiday rentals
- Catskill Mountains Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
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- Pet-friendly rentals New York
- Pet-friendly rentals New Hampshire
- Pet-friendly rentals Massachusetts
- Rentals with a patio Pittsfield
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- Pet-friendly rentals Berkshire County
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