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 Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
Jan 6 – 13
Home in Lee
4.9 out of 5 average rating, 206 reviews1817 Berkshire Farmhouse- Close to Everything.
Oct 3 – 10
Home in Woodstock
4.91 out of 5 average rating, 641 reviewsDutch Touch Woodstock Cottage
Mar 5 – 12
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Aug 30 – Sep 6
Home in Germantown
4.95 out of 5 average rating, 364 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Oct 10 – 17
Home in Woodstock
4.94 out of 5 average rating, 271 reviewsWoodstock Historic Artist Estate - The Pond House
Mar 18 – 25
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Nov 17 – 24
Home in Hudson
4.86 out of 5 average rating, 132 reviews19th Century Mill House with River View
Sep 25 – Oct 2
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
Nov 3 – 10
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 22 – 29
Barn in Hillsdale
4.97 out of 5 average rating, 117 reviewsHudson Valley Hilltop Barn
May 16 – 23
Cottage in Newfane
4.99 out of 5 average rating, 178 reviewsCozy Vermont Antique Sugar House with Fireplace
Jun 12 – 19
Tiny home in Ghent
4.96 out of 5 average rating, 139 reviewsCountry Getaway Tiny House in woods w/Pool/Sauna
May 27 – Jun 3
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Jul 21 – 28
Farm stay in Saugerties
4.97 out of 5 average rating, 137 reviewsSpring Farm Escape: Animals, Sauna & Mountain View
Sep 17 – 24
Cottage in Rhinebeck
4.87 out of 5 average rating, 147 reviewsSecluded peaceful loft in barn by woods
Nov 28 – Dec 5
Private, pet-friendly home rentals
Apartment in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Nov 28 – Dec 5
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Feb 15 – 22
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Nov 7 – 14
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Nov 3 – 10
Apartment in Sheffield
4.92 out of 5 average rating, 123 reviewsPrivate Berkshire Barn Apartment
May 17 – 24
Apartment in Dummerston
4.96 out of 5 average rating, 163 reviewsHeART Barn Retreat
Sep 14 – 21
Guest suite in Montague
4.93 out of 5 average rating, 164 reviewsGreat Falls Private Suite
Sep 15 – 22
Cabin in Bennington
4.81 out of 5 average rating, 105 reviewsVermont Cabin - Secluded Woods on South Stream
Sep 20 – 27
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
ﺩ.ﺇ37 before taxes and fees
Destinations to explore
- New City Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Catskill Vacation rentals
- Albany Vacation rentals
- Catskill Mountains Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Pet-friendly rentals New York
- Pet-friendly rentals New Hampshire
- Pet-friendly rentals Massachusetts
- Kid-friendly rentals Pittsfield
- Rentals with pools Pittsfield
- Apartment rentals Pittsfield
- House rentals Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a fireplace Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with a patio Pittsfield
- Waterfront rentals Pittsfield
- Rentals with outdoor seating Pittsfield
- Rentals with a washer and dryer Pittsfield
- Rentals with lake access Pittsfield
- Monthly Rentals Pittsfield
- Pet-friendly rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom