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.
Home in Lee
4.89 out of 5 average rating, 234 reviewsCozy 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
Home in Canaan
5.0 out of 5 average rating, 132 reviewsCountry 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
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County pet-friendly home rentals
Pet-friendly house rentals
Home in Lee
4.9 out of 5 average rating, 202 reviews1817 Berkshire Farmhouse- Close to Everything.
Sep 4 – 11
Home in Lenox
4.93 out of 5 average rating, 203 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep 15 – 22
Home in Cheshire
4.86 out of 5 average rating, 198 reviews19th c. Barn in The Berkshires
Apr 11 – 18
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Jan 20 – 27
Home in Pittsfield
4.87 out of 5 average rating, 246 reviewsDancing Horse Lodge
Feb 5 – 12
Home in Williamstown
4.8 out of 5 average rating, 169 reviewsWalking distance to downtown
Dec 6 – 13
Home in Pittsfield
4.97 out of 5 average rating, 112 reviewsCharming Gem in Heart of the Berkshires
Apr 15 – 22
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
May 2 – 9
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Oct 16 – 23
Home in Egremont
4.96 out of 5 average rating, 102 reviewsThe Berkshires Mountain Terrace LUX Home Sleeps 7
Jun 5 – 12
Home in Lenox
4.87 out of 5 average rating, 127 reviewsColonial House, w/Yard,7min walk to Downtown Lenox
Jan 18 – 25
Home in Becket
4.84 out of 5 average rating, 144 reviewsNew, open home at Forest's edge
Nov 29 – Dec 6
Pet-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 201 reviewsHollywood Bungalow in the Berkshires
Jan 30 – Feb 6
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
May 7 – 14
Guest suite in Great Barrington
5.0 out of 5 average rating, 42 reviewsSweet 1-bedroom with salt water pool
Jun 6 – 13
Apartment in Great Barrington
5.0 out of 5 average rating, 13 reviewsKing Bed | Stylish | Wi-Fi | *2m Ski Resort*
Apr 20 – 27
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Oct 31 – Nov 7
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Mar 14 – 21
Home in Egremont
5.0 out of 5 average rating, 24 reviewsMountain View Estate Sleeps 18
Apr 1 – 8
Home in Canaan
4.99 out of 5 average rating, 68 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Oct 29 – Nov 5
Cabin in Sand Lake
5.0 out of 5 average rating, 19 reviews"The Cabin" - Cozy & Rustic Home (Averill Park)
Nov 29 – Dec 6
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Aug 12 – 19
Home in West Stockbridge
5.0 out of 5 average rating, 18 reviewsBerkshire House on the Hill
Jan 9 – 16
Condo in Hancock
4.9 out of 5 average rating, 20 reviewsAll-season Berkshires ski resort condo - Sitzmark
Oct 5 – 12
Private, pet-friendly home rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 248 reviewsWildlife Lakeside Cottage
Nov 3 – 10
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Jun 20 – 27
Cabin in Canaan
4.98 out of 5 average rating, 132 reviewsNewly Renovated Cabin in the Country
Sep 2 – 9
Cottage in Sheffield, The Berkshires
4.93 out of 5 average rating, 100 reviewsCheerful 3-bedroom cottage with woodstove.
Dec 1 – 8
Guesthouse in North Adams
5.0 out of 5 average rating, 204 reviewsNetherwood - North Adams Guest House with Views
Oct 14 – 21
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsCozy cabin with panoramic views in the Berkshires
Sep 11 – 18
Cottage in Williamstown
4.9 out of 5 average rating, 164 reviewsCute Cozy Comfy Cottage in the Berkshires
Dec 7 – 14
Apartment in Lenox
4.95 out of 5 average rating, 105 reviewsLovely Downtown Lenox apt, walk to everything!
Oct 26 – Nov 2
Cabin in North Adams
4.93 out of 5 average rating, 143 reviewsThe Wampanoag Cabin @ The Wigwam Western Summit
Aug 28 – Sep 4
Apartment in Canaan
4.96 out of 5 average rating, 79 reviewsQueechy Lake Carriage House
May 30 – Jun 6
Home in Adams
4.91 out of 5 average rating, 64 reviewsMountain View Hideaway
Feb 11 – 18
Apartment in New Lebanon
5.0 out of 5 average rating, 8 reviewsFolk Art Studio: 1-bedroom near the Berkshires
Oct 24 – 31
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