Pet-friendly holiday rentals in Stockbridge

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Stockbridge

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

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Guest favourite

Cottage in Averill Park

4.95 out of 5 average rating, 136 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Guest favourite

Guest suite in Richmond

4.93 out of 5 average rating, 183 reviews

Tanglewood/Private Ranch/Kid&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!

Superhost

Home in Great Barrington

4.83 out of 5 average rating, 108 reviews

Great Barrington, Cabin Sleeps 14, Walk To Town

You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!

Guest favourite

Cottage in Williamstown

4.9 out of 5 average rating, 186 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Top guest favourite

Flat in Pine Plains

4.98 out of 5 average rating, 168 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Superhost

Holiday home in Hudson

4.85 out of 5 average rating, 128 reviews

Bright and Airy 2 blocks from Warren ST eb

Experience comfort and convenience in this Hudson apartment, perfect for solo travelers, couples, or small families. Enjoy the cozy ambiance of this space, complete with a fully equipped kitchen, and organic washing and cleaning products. You'll find comfortable sleeping arrangements, as well as Smart TV and board/card games for your entertainment. Unwind on your private patio. Whether you're here for business or leisure, don't miss out on this spacious, bright, peaceful space.

Guest favourite

Campervan/Motorhome in Germantown

4.88 out of 5 average rating, 179 reviews

Vintage Shasta at Gatherwild Ranch

This lovingly restored 1963 Shasta Camper is a fun and unique experience. Complete with all original curved plywood detailing, enjoy a cute & kitschy throwback equipped with 2 full size beds, original kitchen with working propane stove, sink, electricity and fans. The design is breezy with lots of windows and air throughout. Outside enjoy a private table, firepit, and Adirondack chairs and all the amenities of Gatherwild Ranch including stand alone clawfoot tubs.

Superhost

Home in Hillsdale

4.89 out of 5 average rating, 139 reviews

Fenced yard, playroom & the Berkshires - $0 fees

Enjoy our 8.5 acre, private home. It's a great place to either relax, or enjoy nature whether it's skiing, hiking, kayaking, or biking. Ample space for numerous groups, including an enclosed backyard with grill and fire pit. 4 bedrooms and 3 baths For hikers, Taconic State Park :06 For bikers, Harlem Vally Rail Trail :08 For skiers, Catamount :05 ~2.5 hours from NYC and Boston ~ 15 min to Great Barrington, MA ~25 min to Hudson, NY ~20 min to Millerton, NY

Guest favourite

Home in Albany

4.91 out of 5 average rating, 222 reviews

Modern home, King Bed 4 bed 2bath, Crib, parking

Come relax at a Hidden Gem in the heart of Albany, NY. It is centrally located between Albany Med hospitals and Saint Peters Hospital and in close proximity to the downtown college campuses of UAlbany, Saint Rose, Albany Pharmaceutical, Albany Law school and medical school, and the New York State capital. Some of the best restaurants and pubs are just minutes from this central location. It is only a 15-minute ride to the Albany International Airport.

Guest favourite

Home in Germantown

4.97 out of 5 average rating, 326 reviews

Fantastic Cottage/Insane Views/Trails/Fireplace!

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

Guest favourite

Flat in Hawley

4.89 out of 5 average rating, 146 reviews

Green Acres Hawley Upper Studio (Bonus Room)

This space is a Large Studio Apartment in the Bonus Room above the Garage of a large log home overlooking Berkshire East Mountain Resort. Guests have shared access to the hot tub, deck, fire pit barbecue area and limited access to host's laundry facilities. You'll have sole access to the bonus room, deck & grill and full private bath. Space is comfy and charming, accessible from a private staircase or spiral into the main house's entrance hall.

Guest favourite

Cottage in Lanesborough

4.84 out of 5 average rating, 278 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016) CURRENTLY BEING UPDATED and RENOVATED, (March and April 2025!) private cottage set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. For conditions message Jill.