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
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)
May 22 – 29
$117 per night
4.89 out of 5 average rating, 234 reviews
Guest favorite
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.
Nov 1 – 8
$135 per night
5.0 out of 5 average rating, 130 reviews
Guest favorite
Apartment in Copake Falls
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!
Aug 17 – 24
$104 per night
4.93 out of 5 average rating, 247 reviews

Popular amenities for Berkshire County pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
Jun 23 – 30
$225 per night
4.89 out of 5 average rating, 199 reviews
Guest favorite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Jan 18 – 25
$329 per night
4.92 out of 5 average rating, 168 reviews
Guest favorite
Home in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
Jun 6 – 13
$221 per night
4.93 out of 5 average rating, 203 reviews
Guest favorite
Home in Great Barrington
Your own private Berkshires retreat
Apr 17 – 24
$218 per night
4.9 out of 5 average rating, 111 reviews
Guest favorite
Home in Cheshire
Ski at 19th c. Barn in The Berkshires
Feb 17 – 24
$338 per night
4.85 out of 5 average rating, 196 reviews
Guest favorite
Home in Huntington
Private house on the River
May 6 – 13
$165 per night
4.9 out of 5 average rating, 108 reviews
Guest favorite
Home in New Marlborough
Lake House in the Berkshire (4min to Ski ButterNut
Apr 28 – May 5
$222 per night
4.89 out of 5 average rating, 122 reviews
Guest favorite
Home in Pittsfield
Charming Gem in Heart of the Berkshires
Apr 17 – 24
$160 per night
4.97 out of 5 average rating, 112 reviews
Guest favorite
Home in Lenox
Colonial House, w/Yard,7min walk to Downtown Lenox
Oct 30 – Nov 6
$307 per night
4.87 out of 5 average rating, 125 reviews
Guest favorite
Home in Egremont
The Berkshires Mountain Terrace LUX Home Sleeps 7
Aug 17 – 24
$664 per night
4.96 out of 5 average rating, 100 reviews
Guest favorite
Home in North Adams
Brooklyn Zoo: Unique retreat in the Berkshires
Aug 22 – 29
$196 per night
4.96 out of 5 average rating, 202 reviews
Guest favorite
Home in West Stockbridge
Peaceful Stockbridge Cabin in the Woods
Mar 22 – 29
$238 per night
4.87 out of 5 average rating, 102 reviews

Pet-friendly home rentals with a pool

Guest favorite
Barn in Hillsdale
Hudson Valley Hilltop Barn
Apr 13 – 20
$869 per night
4.97 out of 5 average rating, 115 reviews
Guest favorite
Bungalow in Williamstown
Hollywood Bungalow in the Berkshires
Dec 15 – 22
$204 per night
4.89 out of 5 average rating, 201 reviews
Guest favorite
Home in Sheffield
Race Mountain House
Jul 25 – Aug 1
$483 per night
4.85 out of 5 average rating, 114 reviews
Guest favorite
Home in Great Barrington
Newly Remodeled Private Estate-Pool, Tennis Court!
Nov 5 – 12
$925 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Guest suite in Great Barrington
Sweet 1-bedroom with salt water pool
Jun 19 – 26
$133 per night
5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
Oct 5 – 12
$274 per night
4.96 out of 5 average rating, 56 reviews
Guest favorite
Apartment in Great Barrington
King Bed|2mi Ski Resort|Fast Wi-Fi|Studio|
Mar 14 – 21
$143 per night
4.92 out of 5 average rating, 13 reviews
Guest favorite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Nov 26 – Dec 3
$736 per night
4.99 out of 5 average rating, 68 reviews
Guest favorite
Home in Pittsfield
Stunning Berkshires Retreat, Large and Private
Jan 19 – 26
$616 per night
5.0 out of 5 average rating, 40 reviews
Guest favorite
Cabin in Sand Lake
"The Cabin" - Cozy & Rustic Home (Averill Park)
Dec 26 – Jan 2
$222 per night
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in West Stockbridge
Berkshire House on the Hill
Dec 14 – 21
$925 per night
5.0 out of 5 average rating, 18 reviews
Superhost
Cabin in Sandisfield
Iconic Cabin in the Berkshires
Apr 12 – 19
$990 per night
4.85 out of 5 average rating, 41 reviews

Private, pet-friendly home rentals

Guest favorite
Cottage in Becket
Cozy lakeside cottage
Aug 27 – Sep 3
$457 per night
4.95 out of 5 average rating, 117 reviews
Guest favorite
Cottage in Becket
BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
Dec 21 – 28
$164 per night
4.94 out of 5 average rating, 236 reviews
Guest favorite
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
Jul 18 – 25
$77 per night
4.86 out of 5 average rating, 134 reviews
Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
Jul 28 – Aug 4
$116 per night
4.92 out of 5 average rating, 118 reviews
Superhost
Cottage in Lanesborough
Wildlife Lakeside Cottage
Oct 27 – Nov 3
$241 per night
4.85 out of 5 average rating, 246 reviews
Guest favorite
Cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
Apr 20 – 27
$126 per night
4.9 out of 5 average rating, 164 reviews
Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
Apr 26 – May 3
$248 per night
4.81 out of 5 average rating, 243 reviews
Guest favorite
Guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
Jan 25 – Feb 1
$144 per night
4.93 out of 5 average rating, 166 reviews
Guest favorite
Cabin in Canaan
Newly Renovated Cabin in the Country
Sep 18 – 25
$293 per night
4.98 out of 5 average rating, 132 reviews
Guest favorite
Cabin in Lee
Spring fever! Cabin with views in the Berkshires
Nov 15 – 22
$338 per night
4.9 out of 5 average rating, 102 reviews
Superhost
Cabin in North Adams
The Wampanoag Cabin @ The Wigwam Western Summit
Jul 17 – 24
$206 per night
4.93 out of 5 average rating, 143 reviews
Guest favorite
Apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
Mar 15 – 22
$60 per night
4.83 out of 5 average rating, 151 reviews

Destinations to explore