Pet-friendly vacation 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 favorite

A cozy cottage is surrounded by lush greenery, featuring a well-manicured lawn and colorful flower beds. A stone structure with a roof is positioned in the foreground. The cottage showcases a welcoming porch with seating and a white door, under a partly cloudy blue sky.

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 favorite

A serene view of a horse ranch featuring grazing horses in a lush green field. A charming wooden house with a modern addition is nestled among trees, displaying large windows and a front patio area. A wooden fence outlines the property, enhancing the peaceful rural setting.

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

A spacious living room features a large U-shaped leather couch and a central ottoman, offering seating for several guests. Natural light pours through multiple windows, highlighting the wooden walls and stone accents. The kitchen area is visible in the background, enhancing the open layout.

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 favorite

A charming blue cottage with a wooden fence is showcased, featuring an American flag mounted on the front. The entrance includes a door framed by two windows, and a rustic fence leads to the path, surrounded by autumn leaves and forest greenery.

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 favorite

The kitchen features modern white cabinetry with black handles, complemented by a light-colored countertop. A stainless steel sink is positioned under a wall-mounted faucet. A tile backsplash in neutral tones adds texture, while a fire extinguisher is mounted for safety.

Apartment in Pine Plains

4.98 out of 5 average rating, 167 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

A spacious bedroom features a light grey bed with simple bedding. A colorful wall art piece adds character to one side, while a desk and chair occupy the other. Natural light filters through the large window, and warm wood flooring complements the overall design.

Vacation 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 favorite

Camper/RV 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

A single-story house is set on a grassy lot, featuring a sloped roof and multiple large windows. A driveway leads to a garage, while low shrubs border the front. A clear sky is visible above, with scattered clouds adding dimension.

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 favorite

A sunny view of the country cottage’s exterior showcases a large, grassy yard framed by a mature tree. The inviting porch features a couple of wooden chairs, while pastures and trees extend into the distance, creating a serene rural setting.

Cottage in North East

4.87 out of 5 average rating, 151 reviews

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. An idyllic setting in which to unplug and enjoy nature. Walk to the 42-mile Rail Trail, strap your bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventure!

Guest favorite

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

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 favorite

A serene nighttime view of the log home showcases illuminated windows against a dark sky, with snow gently covering the ground. A warm glow emanates from the outdoor area, highlighting a stone fire pit. Trees are silhouetted, adding depth to the picturesque landscape.

Apartment in Hawley

4.89 out of 5 average rating, 145 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 favorite

A cozy living area is visible, featuring a sofa and a coffee table, with a decorative rug underneath. A large sliding glass door opens to a wooden deck, permitting views of the surrounding nature. A dog sits patiently by the door, observing the outdoors.

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.

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What guests are saying

Light-filled Warren St Apartment

4.95 out of 5 average rating, 39 reviews3 months ago

We had a great stay at William’s with our infant! The apartment was a comfortable size with a laundry room and in a great location walking distance to everything! The only thing was that there wasn’t a crib as listed, so make sure to bring a pack and play if you’re bringing an infant!

Apartment in Hudson

What guests are saying

Charming home ready for fun and/or relaxation!

4.8 out of 5 average rating, 10 reviews2 months ago

We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!

Home in Litchfield County

What guests are saying

Yellow Door House

4.92 out of 5 average rating, 60 reviews6 months ago

Yellow Door House was a fantastic stay, paired with an even more incredible host. The house itself was well-furnished and clean, with plenty of extra house supplies for us to use. Kathleen was also impeccable as a host, going above and beyond to make sure we had a great experience; one of our party left behind a water bottle, and she was so accommodating as to ship it back to us. I could not recommend this place more!

Home in Copake

What guests are saying

Cozy Chic Home, Hot Tub, Near Warren St

4.76 out of 5 average rating, 212 reviews2 months ago

We had a great stay in Hudson! It's a great town and we were in an ideal location--plus it really felt like we were coming "home" at the end of each day. Very cozy feeling during some snowy and icy days!!!!! We found it very relaxing and had a wonderful visit!

Home in Hudson

What guests are saying

Copake Lake & Catamount/Berkshires Cottage

4.85 out of 5 average rating, 144 reviews2 weeks ago

We thoroughly enjoyed our stay at this comfortable and well-equipped Airbnb. The location was perfect for exploring the surrounding area. Everything was spotlessly clean and the host had provided thoughtful touches throughout. We especially appreciated the easy check-in process and clear communication. We highly recommend this property to future guests.

Bungalow in Hillsdale

What guests are saying

Summer & Leaf Season Rental!

5 out of 5 average rating, 6 reviews3 months ago

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

Home in Great Barrington

What guests are saying

Catskill Ski Hike Lake Pet Main St Pool

4.99 out of 5 average rating, 71 reviews2 months ago

The house is beautifully renovated with a stylish design. It had everything we needed, including kitchen and bathroom essentials, as well as complimentary coffee, tea, and snacks. We especially appreciated the thoughtful baby-friendly amenities like a high chair, bathtub, installed baby gates, and toys—it made traveling so much easier without having to bring these from home. The space was spotless, cozy, and well-organized. As we traveled with kids and several families the soundproofing was a bit challenging for us. But for sure it is a great house for family gateway. Patricia was incredibly welcoming and responded quickly to all our inquiries. The location is also very convenient —just one street away from the main road, making it easy to access cafes and shops. And once you explored the Catskills it is very easy to reach Hudson (10 min by car). We enjoyed our stay a lot.

Home in Catskill

What guests are saying

Rabbit Run in the heart of Stockbridge Village

4.89 out of 5 average rating, 96 reviews2 months ago

Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!

Home in Stockbridge

What guests are saying

French country cottage, fireplace & hottub

5 out of 5 average rating, 39 reviews8 months ago

Kerri is an amazing host. We rented all of her properties for our wedding. More than any other Airbnb host we have ever had, Kerri truly makes you feel like the space is yours. The house and property are so clean, perfectly decorated, and comfortable. She is so responsive and accommodating, and just so friendly. She has great recommendations for local places. We have fell in love with Coxsackie! We will be back!

Cabin in West Coxsackie

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