Pet-friendly vacation rentals in Berkshire County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Berkshire County

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

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

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)

Sep 13 – 20

$108 per night
Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

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.

Dec 27 – Jan 3

$135 per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 13 – 20

$88 per night

Popular amenities for Berkshire County pet-friendly home rentals

Pet-friendly house rentals

Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

Sep 4 – 11

$221 per night
Guest favorite

Home in Lenox

4.93 out of 5 average rating, 203 reviews

Heart of Lenox Walk to Town Cozy Cottage!

Sep 15 – 22

$374 per night
Guest favorite

Home in Cheshire

4.86 out of 5 average rating, 198 reviews

19th c. Barn in The Berkshires

Apr 11 – 18

$338 per night
Guest favorite

Home in Huntington

4.9 out of 5 average rating, 109 reviews

Private house on the River

Jan 20 – 27

$165 per night
Guest favorite

Home in Pittsfield

4.87 out of 5 average rating, 246 reviews

Dancing Horse Lodge

Feb 5 – 12

$157 per night
Guest favorite

Home in Williamstown

4.8 out of 5 average rating, 169 reviews

Walking distance to downtown

Dec 6 – 13

$139 per night
Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 112 reviews

Charming Gem in Heart of the Berkshires

Apr 15 – 22

$160 per night
Guest favorite

Home in New Marlborough

4.89 out of 5 average rating, 122 reviews

Lake House in the Berkshire (Access Dock & Canoe

May 2 – 9

$238 per night
Superhost

Home in Great Barrington

4.9 out of 5 average rating, 111 reviews

Your own private Berkshires retreat

Oct 16 – 23

$304 per night
Guest favorite

Home in Egremont

4.96 out of 5 average rating, 102 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

Jun 5 – 12

$589 per night
Guest favorite

Home in Lenox

4.87 out of 5 average rating, 127 reviews

Colonial House, w/Yard,7min walk to Downtown Lenox

Jan 18 – 25

$268 per night
Superhost

Home in Becket

4.84 out of 5 average rating, 144 reviews

New, open home at Forest's edge

Nov 29 – Dec 6

$151 per night

Pet-friendly home rentals with a pool

Guest favorite

Bungalow in Williamstown

4.89 out of 5 average rating, 201 reviews

Hollywood Bungalow in the Berkshires

Jan 30 – Feb 6

$204 per night
Guest favorite

Home in Sheffield

4.85 out of 5 average rating, 114 reviews

Race Mountain House

May 7 – 14

$483 per night
Guest favorite

Guest suite in Great Barrington

5.0 out of 5 average rating, 42 reviews

Sweet 1-bedroom with salt water pool

Jun 6 – 13

$136 per night
Guest favorite

Apartment in Great Barrington

5.0 out of 5 average rating, 13 reviews

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Apr 20 – 27

$108 per night
Guest favorite

Home in Great Barrington

4.97 out of 5 average rating, 33 reviews

Newly Remodeled Private Estate-Pool, Tennis Court!

Oct 31 – Nov 7

$925 per night
Guest favorite

Home in Pittsfield

5.0 out of 5 average rating, 41 reviews

Stunning Berkshires Retreat, Large and Private

Mar 14 – 21

$623 per night
Guest favorite

Home in Egremont

5.0 out of 5 average rating, 24 reviews

Mountain View Estate Sleeps 18

Apr 1 – 8

$395 per night
Guest favorite

Home in Canaan

4.99 out of 5 average rating, 68 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

Oct 29 – Nov 5

$771 per night
Guest favorite

Cabin in Sand Lake

5.0 out of 5 average rating, 19 reviews

"The Cabin" - Cozy & Rustic Home (Averill Park)

Nov 29 – Dec 6

$222 per night
Guest favorite

Home in Pittsfield

4.96 out of 5 average rating, 56 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

Aug 12 – 19

$679 per night
Guest favorite

Home in West Stockbridge

5.0 out of 5 average rating, 18 reviews

Berkshire House on the Hill

Jan 9 – 16

$925 per night
Guest favorite

Condo in Hancock

4.9 out of 5 average rating, 20 reviews

All-season Berkshires ski resort condo - Sitzmark

Oct 5 – 12

$175 per night

Private, pet-friendly home rentals

Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 248 reviews

Wildlife Lakeside Cottage

Nov 3 – 10

$238 per night
Guest favorite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 reviews

Sunny Berkshire Studio Apartment

Jun 20 – 27

$113 per night
Guest favorite

Cabin in Canaan

4.98 out of 5 average rating, 132 reviews

Newly Renovated Cabin in the Country

Sep 2 – 9

$293 per night
Guest favorite

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 100 reviews

Cheerful 3-bedroom cottage with woodstove.

Dec 1 – 8

$223 per night
Guest favorite

Guesthouse in North Adams

5.0 out of 5 average rating, 204 reviews

Netherwood - North Adams Guest House with Views

Oct 14 – 21

$187 per night
Guest favorite

Cabin in Lee

4.9 out of 5 average rating, 102 reviews

Cozy cabin with panoramic views in the Berkshires

Sep 11 – 18

$339 per night
Guest favorite

Cottage in Williamstown

4.9 out of 5 average rating, 164 reviews

Cute Cozy Comfy Cottage in the Berkshires

Dec 7 – 14

$150 per night
Guest favorite

Apartment in Lenox

4.95 out of 5 average rating, 105 reviews

Lovely Downtown Lenox apt, walk to everything!

Oct 26 – Nov 2

$275 per night
Superhost

Cabin in North Adams

4.93 out of 5 average rating, 143 reviews

The Wampanoag Cabin @ The Wigwam Western Summit

Aug 28 – Sep 4

$212 per night
Guest favorite

Apartment in Canaan

4.96 out of 5 average rating, 79 reviews

Queechy Lake Carriage House

May 30 – Jun 6

$85 per night
Guest favorite

Home in Adams

4.91 out of 5 average rating, 64 reviews

Mountain View Hideaway

Feb 11 – 18

$104 per night
Guest favorite

Apartment in New Lebanon

5.0 out of 5 average rating, 8 reviews

Folk Art Studio: 1-bedroom near the Berkshires

Oct 24 – 31

$100 per night

Destinations to explore