Pet-friendly vacation rentals in Stockbridge

4.95 out of 5 average rating, 317 reviews

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

WalkabilityOutdoor spacesBreakfast

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

4.95 out of 5 average rating, 187 reviews

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Outdoor spacesPetsAmenities

Apartment in Great Barrington

A modern bedroom showcases a spacious bed with crisp white linens. Accent lighting frames the walls, and a patterned area rug adds warmth to the space. A compact seating area with stylish benches complements the décor, while an entrance leads to a private bathroom.

4.92 out of 5 average rating, 165 reviews

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Outdoor spacesWalkabilityHeating

4.97 out of 5 average rating, 101 reviews

Cabin in East Nassau

Luxury Cabin - Fall Foliage & Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

Outdoor spacesPetsGrill

Guesthouse in Great Barrington

A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.

4.95 out of 5 average rating, 172 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

PetsOutdoor spacesQuiet

4.96 out of 5 average rating, 111 reviews

An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.

Barn in East Chatham

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed retreat combines dramatic contemporary design with warmth and comfort. Soaring ceilings, a chef’s kitchen, designer interiors, peaceful outdoor spaces and nearby lake access create the perfect escape. Ideal for couples, families with children or close friends, it’s a short drive from Hudson, Chatham, Great Barrington, Tanglewood and countless other destinations for shopping, dining, hiking and more.

PetsOutdoor spacesAccuracy

Guesthouse in Stockbridge

A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.

4.9 out of 5 average rating, 168 reviews

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

WalkabilityOutdoor spacesLayout

Tiny home in New Marlborough

4.94 out of 5 average rating, 191 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Outdoor spacesPetsHospitality

4.95 out of 5 average rating, 149 reviews

The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.

Apartment in Lenox

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

WalkabilityOutdoor spacesLong stay

4.96 out of 5 average rating, 394 reviews

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

Scandinavian Cottage/Mountain Views/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ 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!

Outdoor spacesWalkabilityQuiet

A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.

4.89 out of 5 average rating, 125 reviews

Rabbit Run in the heart of Stockbridge Village

Old meets new in this lovely cottage, a short walk from the Red Lion Inn. Lots of light, comfortable, traditional furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park, and tennis courts within a 5-minute walk. Lake rights to Stockbridge Bowl, Weber grill, and Solo firepit.

Outdoor spacesPetsCleanliness

4.94 out of 5 average rating, 124 reviews

A circular stone entryway frames a winding path leading to a quaint cabin nestled among tall trees. Sunlight filters through the forest canopy, casting a gentle glow on the surrounding greenery.

Guesthouse in Lenox

The East Street Cabin

This adorable cabin is your perfect escape for rest and relaxation. This is a perfect place for people coming to the Berkshires for Tanglewood or any of the other wonderful things the area has to offer. The cabin is located down a path through the woods about 100 yards from the main house. We are excited to share our cabin with you.

WalkabilityPetsLayout

Popular amenities for Stockbridge pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5.0 out of 5 average rating, 113 reviews

A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.

Home in Becket

Cozy lakehouse

PetsOutdoor spacesHiking

4.97 out of 5 average rating, 138 reviews

A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.

Home in Lee

Stylish Mid-century Modern Berkshires Cape

Outdoor spacesPetsCheckout

4.95 out of 5 average rating, 131 reviews

Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

WalkabilityOutdoor spacesHeating

4.95 out of 5 average rating, 495 reviews

A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.

Home in Germantown

Rustic Swedish Barn/Featured in Airbnb Magazine

PetsWalkabilityAmenities

4.88 out of 5 average rating, 107 reviews

A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.

Home in Lee

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Outdoor spacesPetsComfort

4.99 out of 5 average rating, 384 reviews

A charming two-story red house is surrounded by lush greenery and colorful flowering plants. Sturdy steps lead up to the entrance, framed by vibrant shrubs and hydrangeas, creating a welcoming outdoor area that blends naturally with the landscape.

Home in New Lebanon

The old sawmill from 1771

WalkabilityOutdoor spacesFamily

4.86 out of 5 average rating, 126 reviews

Home in West Stockbridge

Peaceful Stockbridge Cabin in the Woods

PetsOutdoor spacesQuiet

4.99 out of 5 average rating, 129 reviews

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

Home in Great Barrington

Private Home in The Berkshires (New Hot Tub!)

WalkabilityPetsWifi

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 392 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

Outdoor spacesWalkabilityShared spaces

4.95 out of 5 average rating, 169 reviews

A modern tiny house is surrounded by tall trees, with warm light emanating from its large windows. The sleek black exterior contrasts with the natural greenery, creating a blend of contemporary design and serene nature. The rising dusk hints at a tranquil evening.

Tiny home in Ghent

Country Getaway Tiny House in woods w/Pool/Sauna

Outdoor spacesPetsHeating

4.92 out of 5 average rating, 106 reviews

The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

Outdoor spacesPetsAir conditioning

4.96 out of 5 average rating, 130 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

PetsOutdoor spacesBathroom

4.98 out of 5 average rating, 100 reviews

A peaceful backyard is featured, showcasing two green swings suspended from a sturdy frame. The grassy lawn is bordered by a wooden fence, and a relaxing seating area with a lounge chair is visible in the background, surrounded by greenery and trees.

Home in Catskill

Catskill Village Ski Hike Lake Pet Main St Pool

PetsOutdoor spacesLong stay

4.95 out of 5 average rating, 168 reviews

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

PetsWalkabilityHeating

4.98 out of 5 average rating, 106 reviews

A spacious hot tub is positioned under a wooden pavilion, surrounded by string lights. Water cascades gently inside, with soft lighting reflecting on the surface. In the background, a tranquil view of the lake and nearby seating areas can be seen, inviting relaxation.

Home in Athens

Hudson Valley Lake · Hot Tub · Dock · Games · View

WalkabilityPetsAmenities

4.83 out of 5 average rating, 121 reviews

Two framed art pieces featuring feathers are displayed on a weathered wood wall. Above the artwork, a mounted skull adds a rustic touch to the design. The arrangement showcases natural elements that blend seamlessly with the cottage's decor.

Cottage in Hudson

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

PetsOutdoor spacesCleanliness

Private, pet-friendly home rentals

5.0 out of 5 average rating, 103 reviews

Tiny home in Chatham

Romantic-Private-Western Tiny Cabin w/HOT TUB

Outdoor spacesWalkabilityGetting around

Cabin in Great Barrington

A charming log cabin sits nestled among lush greenery, showcasing a sloped roof and multiple windows. A spacious deck extends from the front, providing an outdoor area surrounded by trees. Natural light filters through the foliage, highlighting the cabin's rustic wooden exterior.

4.97 out of 5 average rating, 115 reviews

Modern Luxury Log Cabin

WalkabilityOutdoor spacesDecor

Treehouse in New Marlborough

The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.

4.91 out of 5 average rating, 170 reviews

Berkshire Treehouse Retreat

PetsWalkabilityNearby

A bright living area features large windows that allow natural light to flood in, showcasing views of nearby trees in autumnal colors. Two modern armchairs and a navy sofa are arranged on a patterned area rug, with a coffee table positioned centrally.

4.95 out of 5 average rating, 42 reviews

Stockbridge pied-à-terre

WalkabilityPetsWifi

4.93 out of 5 average rating, 95 reviews

A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.

Apartment in Stockbridge

Stockbridge private apartment

PetsWalkabilityDecor

4.98 out of 5 average rating, 64 reviews

A hammock is gently draped between trees, overlooking a tranquil pond. Nearby, a dock extends into the water, surrounded by lush greenery and lily pads, providing a serene spot for relaxation and contemplation.

Cabin in Stockbridge

Lakeshore cabin with beach and dock

Outdoor spacesPetsCondition

5.0 out of 5 average rating, 22 reviews

Home in West Stockbridge

Exceptional Stockbridge Retreat

PetsOutdoor spacesGrill

An open living area features cathedral ceilings supported by wooden beams. A mix of bright furniture includes a yellow sofa and a red sectional. Large windows allow ample natural light, illuminating the wooden floors. A cozy wood stove complements the inviting space.