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Pet-friendly holiday rentals in Pittsfield

Find and book unique pet-friendly homes on Airbnb

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Top-rated pet-friendly home rentals in Pittsfield

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

Guest favourite
Home in Canaan
Country Cottage
Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.
23 – 30 Jan
Guest favourite
Home in Lee
Cozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
22 – 29 May
Guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!
10 – 17 Feb

Popular amenities for Pittsfield pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
23 – 30 June
Guest favourite
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
5 – 12 Nov
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
10 – 17 Feb
Guest favourite
Home in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
16 – 23 Aug
Guest favourite
Home in Germantown
Scandinavian Barn Featured in Airbnb Magazine
2 – 9 Mar
Guest favourite
Home in Germantown
Germantown Cottage! Catskills Views! H River trail
28 May – 4 June
Guest favourite
Home in Cheshire
Ski at 19th c. Barn in The Berkshires
9 – 16 May
Guest favourite
Home in Lenox
Colonial House, w/Yard,7min walk to Downtown Lenox
24 – 31 Dec
Home in Northampton
The Farmhouse - Hot tub eclectic farmhouse 3 br
16 – 23 June
Guest favourite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
17 – 24 Feb
Guest favourite
Home in New Ashford
Rosecroft, Historic Home, Greylock Valley Estate
21 – 28 Feb
Guest favourite
Home in Huntington
Private house on the River
28 Apr – 5 May

Pet-friendly home rentals with a pool

Guest favourite
Tiny home in Brattleboro
"Mountain View" Hike In Cabin Retreat
19 – 26 May
Guest favourite
Bungalow in Easthampton
The Creation Station
6 – 13 May
Guest favourite
Cabin in Red Hook
Modern Upstate Cabin, near Rhinebeck NY
24 – 31 May
Guest favourite
Farm stay in Saugerties
Winter Farm Escape: Animals, Sauna & Mountain View
4 – 11 May
Guest favourite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
25 July – 1 Aug
Guest favourite
Home in Saugerties
Wilderkill Catskill Retreat, Mountain Modern Barn
29 Apr – 6 May
Guest favourite
Cottage in Old Chatham
Berkshires / Hudson Loft
2 – 9 Mar
Guest favourite
Farm stay in Red Hook
Sackett & Van Dam Guest House @ Little 9 Farm 1706
5 – 12 Aug
Guest favourite
Bungalow in Williamstown
Hollywood Bungalow in the Berkshires
28 Oct – 4 Nov
Guest favourite
Cottage in Rhinebeck
Secluded peaceful loft in barn by woods
18 – 25 Apr
Guest favourite
Guesthouse in Stanfordville
Eco Cottage in the Woods
5 – 12 Oct
Guest favourite
Farm stay in West Sand Lake
Roundhill Farm - Come Ski With Us!
13 – 20 Feb

Private, pet-friendly home rentals

Guest favourite
Guesthouse in Stephentown
Dog Friendly Studio
4 – 11 Jan
Cottage in Lanesborough
Wildlife Lakeside Cottage
3 – 10 Nov
Guest favourite
Treehouse in Catskill
The Hudson Lookout: Watchtower with Views + Sauna
10 – 17 Dec
Guest favourite
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
12 – 19 May
Guest favourite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
4 – 11 Apr
Cabin in Maplecrest
The Cabin - Ski House near Windham
19 – 26 July
Guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
18 – 25 Dec
Guest favourite
Cabin in Freehold
Tiny Home A-Frame with Hot Tub & Creek
25 June – 2 July
Guest favourite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
16 – 23 Feb
Guest favourite
Barn in Marlboro
The Studio With a View. Bring your dog, too!
23 – 30 Dec
Guest favourite
Loft in East Nassau
Dog Friendly Farm
27 Apr – 4 May
Guest favourite
Cabin in Putney
Vermont Retreat Cottage| Cozy & Romantic Escape
2 – 9 Aug

Quick stats about holiday rentals that are pet-friendly in Pittsfield

Total rentals

70 properties

Rentals with dedicated workspaces

40 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

2.6K reviews

Nightly prices starting at

$15 AUD before taxes and fees

Destinations to explore