Airbnb your place

Pet-friendly holiday rentals in West Stockbridge

Find and book unique pet-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 30 holiday rentals in West Stockbridge

  • Nightly prices starting at

    West Stockbridge holiday rentals start at €132 per night before taxes and fees

  • Verified guest reviews

    Over 860 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of West Stockbridge holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across West Stockbridge rentals

  • 4.9 Average rating

    West Stockbridge stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in West Stockbridge

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

1 of 1 pages1 / 1
Top guest favourite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

PetsOutdoor spacesCheckout

4.99 out of 5 average rating, 159 reviews
Top guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View 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, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

PetsOutdoor spacesLayout

4.97 out of 5 average rating, 110 reviews
Guest favourite
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.
Home in Stockbridge

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 spacesWalkabilityRiver

4.95 out of 5 average rating, 191 reviews
Guest favourite
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 Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

PetsOutdoor spacesLayout

4.96 out of 5 average rating, 114 reviews
Guest favourite
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.
Flat in Stockbridge

Stockbridge private apartment

Newly renovated apartment, just one mile from Downtown Stockbridge. This cozy apartment offers gorgeous mountain views and access to the lush backyard area. 10 minutes from local attractions such as Tanglewood, the Stockbridge bowl, and Kripalu. Close to many hiking trails, including backyard access to a riverside walking trail This apartment is attached to the owners house, however it has a private entrance and is completely separate. The parking area is shared- there is space for two cars.

WalkabilityOutdoor spacesCheckout

4.92 out of 5 average rating, 103 reviews
Guest favourite
A modern bedroom features a spacious bed with high-end linens, flanked by two stylish chairs. A desk and chair sit by the window, and an arched door adds architectural interest. Natural light illuminates the room, highlighting a unique wall design in neutral tones.
Flat in Great Barrington

King Bed | Patio | 2m to 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 spacesPetsLayout

4.91 out of 5 average rating, 186 reviews
Guest favourite
A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.
Guest suite in Richmond

Berkshires/Pet Friendly/Tanglewood/Private Ranch

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 Rides /Horse activities available by appt!

PetsWalkabilityHiking

4.94 out of 5 average rating, 207 reviews
Guest favourite
Guest house in Great Barrington

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.

Outdoor spacesPetsQuiet

4.95 out of 5 average rating, 177 reviews
Guest favourite
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.
Guest house in Stockbridge

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*

PetsOutdoor spacesComfort

4.91 out of 5 average rating, 175 reviews
Guest favourite
Home in West Stockbridge

Peaceful Stockbridge Cabin in the Woods

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

Outdoor spacesPetsCheckout

4.86 out of 5 average rating, 126 reviews
Superhost
The exterior of a two-story yellow house is presented, featuring a front porch with large windows and a central door. A water tower is visible in the background, surrounded by greenery and a gravel pathway leading to the entrance.
Home in Great Barrington

Relaxing Housatonic Retreat

This home is where my husband grew up and has been in his family for many years. It's currently my father-in-law's summer house and is in various stages of updating. The village of Housatonic is one of our favorite places on Earth! With quaint restaurants within a five minute walk, hiking trails nearby, spectacular foliage in the fall, and several ski areas to choose from, it has something for more active people or those who would just like a quiet, relaxing retreat.

PetsWalkabilityDecor

4.7 out of 5 average rating, 128 reviews
Top guest favourite
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

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

PetsOutdoor spacesLocation

4.97 out of 5 average rating, 143 reviews

Popular amenities for West Stockbridge pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favourite
Home in Lenox

Restored 1881 Farm House

Outdoor spacesWalkabilityNearby

4.97 out of 5 average rating, 118 reviews
Superhost
Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

Outdoor spacesWalkabilityCheckout

4.89 out of 5 average rating, 152 reviews
Guest favourite
A charming red house is set against a backdrop of lush greenery. The stone chimney adds a rustic touch, while outdoor seating is arranged on the lawn. A small tower feature enhances the unique architectural design, creating an inviting outdoor space.
Home in Great Barrington

Never too early to book for the Holidays & NYE!

WalkabilityOutdoor spacesFamily

4.91 out of 5 average rating, 143 reviews
Top guest favourite
A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.
Home in Catskill

Cheerful Catskill Village Cottage

PetsWalkabilityCondition

4.97 out of 5 average rating, 235 reviews
Guest favourite
A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.
Home in Hudson

Bright, Airy Home in Hudson w/ TONS of Character!

WalkabilityOutdoor spacesBathroom

4.83 out of 5 average rating, 308 reviews
Top guest favourite
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

Outdoor spacesPetsSleep quality

5.0 out of 5 average rating, 119 reviews
Guest favourite
Home in Chatham

Chatham on the Creek. Pet friendly. F Trump

Outdoor spacesPetsRiver

4.91 out of 5 average rating, 296 reviews
Guest favourite
Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

PetsWalkabilityLocation

4.93 out of 5 average rating, 136 reviews

Pet-friendly home rentals with a pool

Top guest favourite
Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

WalkabilityPetsLaundry

4.97 out of 5 average rating, 185 reviews
Top guest favourite
The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.
Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

PetsOutdoor spacesLong stay

4.98 out of 5 average rating, 136 reviews
Guest favourite
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

PetsOutdoor spacesValue

4.93 out of 5 average rating, 109 reviews
Top guest favourite
A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.
Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

Outdoor spacesPetsSkiing

5.0 out of 5 average rating, 114 reviews
Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

WalkabilityPetsCheck-in

4.88 out of 5 average rating, 222 reviews
Top guest favourite
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

PetsWalkabilityDecor

4.95 out of 5 average rating, 171 reviews
Top guest favourite
A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.
Home in Coxsackie

Hudson River estate guest cottage

Outdoor spacesPetsGrill

4.98 out of 5 average rating, 109 reviews
Top guest favourite
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 spacesPetsAir conditioning

4.96 out of 5 average rating, 398 reviews

Private, pet-friendly home rentals

Top guest favourite
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.

Outdoor spacesWalkabilityFamily

4.95 out of 5 average rating, 320 reviews
Guest favourite
Tiny home in New Marlborough

Bedroom Forest View I Sauna I Fire-pit I Trails

Outdoor spacesWalkabilityParking

4.94 out of 5 average rating, 201 reviews
Guest favourite
An enclosed three-season veranda features wood-paneled walls and a ceiling adorned with beams. Comfortable seating includes a wicker sofa with cushions, a rocking chair, and various potted plants, creating a serene indoor environment filled with natural light from multiple windows.
Cottage in Craryville

Farm Cottage w/ Donkeys, Fire Pit & Wood Stove

PetsOutdoor spacesAccuracy

4.91 out of 5 average rating, 602 reviews
Top guest favourite
A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.
Bungalow in Egremont

3-bedroom Berkshire bungalow on 2.5 peaceful acres

PetsOutdoor spacesFamily

4.99 out of 5 average rating, 143 reviews
Guest favourite
Home in West Stockbridge

Pixley Forest | 15 Mins To Tanglewood • Fireplace

PetsOutdoor spacesCleanliness

4.94 out of 5 average rating, 18 reviews
Top guest favourite
A red brick cottage is set against a backdrop of lush green grass and trees. The home features a gabled roof and large windows. A small, decorative arbor with climbing plants stands in the foreground, providing an inviting entrance to the property.
Home in Canaan

Crossings Cottage

PetsWalkabilityCondition

4.97 out of 5 average rating, 92 reviews
Guest favourite
Home in West Stockbridge

Modern Log Cabin w/Pool & Views By Evergreen Home

Outdoor spacesKitchenHospitality

5.0 out of 5 average rating, 13 reviews
Top guest favourite
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.
Home in Stockbridge

Secluded Family Home in Serene Stockbridge Woods

PetsOutdoor spacesNearby

4.99 out of 5 average rating, 88 reviews

When is the best time to visit West Stockbridge?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€198€246€209€196€187€231€289€289€269€247€248€208
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

Destinations to explore