Pet-friendly vacation rentals in West Stockbridge

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in West Stockbridge

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, 233 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 15 – 22
$98 per night
4.93 out of 5 average rating, 245 reviews
Guest favorite
Guest suite in Richmond
Ski/Private Ranch/Kid friendly/Pet Friendly/Horses
Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!
Mar 29 – Apr 5
$170 per night
4.93 out of 5 average rating, 169 reviews

Popular amenities for West Stockbridge pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
Feb 17 – 24
$373 per night
4.96 out of 5 average rating, 134 reviews
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 Canaan
Country Cottage
Dec 27 – Jan 3
$135 per night
5.0 out of 5 average rating, 129 reviews
Guest favorite
Home in Chatham
Pet-friendly, Chatham, NY. No neighbors in sight.
Oct 28 – Nov 4
$180 per night
4.88 out of 5 average rating, 188 reviews
Guest favorite
Home in Great Barrington
Your own private Berkshires retreat
Feb 6 – 13
$231 per night
4.9 out of 5 average rating, 111 reviews
Guest favorite
Home in Chatham
Country house on Indian Creek
Nov 28 – Dec 5
$145 per night
4.88 out of 5 average rating, 136 reviews
Guest favorite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home.
Feb 19 – 26
$300 per night
4.93 out of 5 average rating, 187 reviews
Guest favorite
Home in Austerlitz
Peaceful Renovated Barn in the Berkshires
Apr 29 – May 6
$273 per night
4.95 out of 5 average rating, 150 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 Pittsfield
Charming Gem in Heart of the Berkshires
Mar 12 – 19
$130 per night
4.97 out of 5 average rating, 112 reviews
Superhost
Home in Ghent
Renovated guesthouse on 52 acres!
Sep 28 – Oct 5
$203 per night
4.9 out of 5 average rating, 255 reviews
Guest favorite
Home in New Marlborough
Lake House in the Berkshire (4min to Ski ButterNut
Apr 25 – May 2
$205 per night
4.89 out of 5 average rating, 122 reviews

Pet-friendly home rentals with a pool

Guest favorite
Guesthouse in Lenox
The Granary at House on Golden Hill
Jun 10 – 17
$180 per night
4.95 out of 5 average rating, 261 reviews
Guest favorite
Barn in Hillsdale
Hudson Valley Hilltop Barn
Apr 13 – 20
$869 per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Cottage in Old Chatham
Berkshires / Hudson Loft
Jun 6 – 13
$134 per night
4.8 out of 5 average rating, 163 reviews
Guest favorite
Cabin in Red Hook
Modern Upstate Cabin, near Rhinebeck NY
Aug 14 – 21
$405 per night
4.96 out of 5 average rating, 300 reviews
Guest favorite
Condo in Windham
Cozy Mountain hideaway Windham, Hunter
May 17 – 24
$78 per night
4.89 out of 5 average rating, 121 reviews
Guest favorite
Tiny home in Ghent
Country Getaway Tiny House in woods w/Pool/Sauna
Mar 22 – 29
$275 per night
4.96 out of 5 average rating, 139 reviews
Guest favorite
Farm stay in Saugerties
Winter Farm Escape: Animals, Sauna & Mountain View
Apr 30 – May 7
$207 per night
4.98 out of 5 average rating, 129 reviews
Guest favorite
Home in Saugerties
Upstate Modern Scandinavian Barn in the Catskills
Sep 24 – Oct 1
$598 per night
5.0 out of 5 average rating, 129 reviews
Guest favorite
Cottage in Rhinebeck
Secluded peaceful loft in barn by woods
Nov 12 – 19
$139 per night
4.87 out of 5 average rating, 140 reviews
Guest favorite
Home in New Paltz
Mid Century Mod *fireplace walk to rail trail/town
Aug 5 – 12
$899 per night
4.98 out of 5 average rating, 430 reviews
Guest favorite
Guesthouse in Stanfordville
Eco Cottage in the Woods
Feb 6 – 13
$119 per night
4.94 out of 5 average rating, 160 reviews
Guest favorite
Home in Woodstock
Little Owl Japanese Teahouse 5 min from Woodstock
Nov 10 – 17
$207 per night
4.91 out of 5 average rating, 199 reviews

Private, pet-friendly home rentals

Guest favorite
Cabin in Canaan
Newly Renovated Cabin in the Country
Apr 15 – 22
$293 per night
4.98 out of 5 average rating, 132 reviews
Guest favorite
Apartment in Sheffield
Private Berkshire Barn Apartment
Apr 23 – 30
$113 per night
4.91 out of 5 average rating, 117 reviews
Guest favorite
Apartment in Petersburg
The Beer Diviner Brewery Apartment
Jan 10 – 17
$59 per night
4.85 out of 5 average rating, 140 reviews
Guest favorite
Cottage in Hillsdale
Cozy Cottage Catamount, Berkshires Walk to Brewery
Aug 16 – 23
$126 per night
4.94 out of 5 average rating, 168 reviews
Guest favorite
Treehouse in Catskill
The Hudson Lookout: Watchtower with Views + Sauna
Dec 19 – 26
$411 per night
5.0 out of 5 average rating, 139 reviews
Guest favorite
Bungalow in Hillsdale
Copake Lake & Catamount/Berkshires Cottage
Mar 27 – Apr 3
$107 per night
4.86 out of 5 average rating, 127 reviews
Guest favorite
Guesthouse in Stephentown
Dog Friendly Studio
Nov 26 – Dec 3
$167 per night
5.0 out of 5 average rating, 352 reviews
Guest favorite
Apartment in Great Barrington
Secluded but not isolated Berkshire Retreat
Jun 24 – Jul 1
$165 per night
4.93 out of 5 average rating, 177 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
Superhost
Cottage in Canaan
Plan your Berkshires by the lake
Apr 1 – 8
$194 per night
4.9 out of 5 average rating, 125 reviews
Guest favorite
Cottage in Becket
Cozy lakeside cottage
Nov 14 – 21
$214 per night
4.95 out of 5 average rating, 117 reviews
Superhost
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
Mar 28 – Apr 4
$252 per night
4.81 out of 5 average rating, 243 reviews

Quick stats about vacation rentals that are pet-friendly in West Stockbridge

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

800 reviews

Nightly prices starting at

$150 before taxes and fees

Destinations to explore