Pet-friendly holiday rentals in West Stockbridge

4.97 out of 5 average rating, 109 reviews

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!

Outdoor spacesPetsAmenities

4.95 out of 5 average rating, 320 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.

Outdoor spacesPetsValue

4.95 out of 5 average rating, 191 reviews

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 spacesWalkabilityCheck-in

4.92 out of 5 average rating, 103 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.

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.

PetsWalkabilityFamily

4.94 out of 5 average rating, 207 reviews

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!

WalkabilityOutdoor spacesValue

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.

WalkabilityOutdoor spacesKitchen

4.95 out of 5 average rating, 176 reviews

Guest house 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.

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*

WalkabilityPetsView

4.91 out of 5 average rating, 175 reviews

4.99 out of 5 average rating, 141 reviews

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

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Outdoor spacesWalkabilityTV

4.86 out of 5 average rating, 126 reviews

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 spacesPetsAir conditioning

4.96 out of 5 average rating, 114 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 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. A private outdoor sauna will be ready for all stays beginning October 1, 2026. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

Outdoor spacesPetsAmenities

Barn in Town of Hillsdale

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

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Outdoor spacesWalkabilityLayout

4.97 out of 5 average rating, 185 reviews

4.91 out of 5 average rating, 601 reviews

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

Welcome to The Cottage at Raspberry Ridge, a charming Hudson Valley farm stay surrounded by gardens, woodlands, donkeys, and chickens. This cozy 3-bedroom retreat blends rustic character with modern comfort, offering a wood-burning stove, peaceful outdoor spaces, and access to the farm grounds. Just minutes from Hudson, Great Barrington, hiking trails, and local farms, it's the perfect place to slow down and reconnect.

PetsOutdoor spacesCheckout

Popular amenities for West Stockbridge pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.97 out of 5 average rating, 118 reviews

Home in Lenox

Restored 1881 Farm House

WalkabilityPetsWifi

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.

4.99 out of 5 average rating, 130 reviews

Private Home in The Berkshires (New Hot Tub!)

WalkabilityPetsCheckout

4.99 out of 5 average rating, 387 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 spacesNearby

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.

4.7 out of 5 average rating, 128 reviews

Relaxing Housatonic Retreat

WalkabilityPetsAmenities

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.

4.91 out of 5 average rating, 142 reviews

Never too early to book for the Holidays & NYE!

WalkabilityPetsGrill

4.89 out of 5 average rating, 127 reviews

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.

Home in Stockbridge

Rabbit Run in the heart of Stockbridge Village

Outdoor spacesWalkabilityAir conditioning

Superhost

Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

WalkabilityPetsValue

4.89 out of 5 average rating, 151 reviews

A two-story wooden house is nestled among lush greenery, featuring a balcony that overlooks the surrounding landscape. Vibrant trees, including a reddish-orange flowering tree, add color to the natural setting, creating a serene atmosphere.

4.89 out of 5 average rating, 102 reviews

Charming, view, large deck, private/walk downtown

Outdoor spacesPetsHiking

Pet-friendly home rentals with a pool

5.0 out of 5 average rating, 114 reviews

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 spacesWalkabilitySkiing

4.98 out of 5 average rating, 109 reviews

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

PetsOutdoor spacesKitchen

4.93 out of 5 average rating, 109 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 spacesPetsNearby

4.95 out of 5 average rating, 171 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

PetsOutdoor spacesSleep quality

4.98 out of 5 average rating, 135 reviews

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

Outdoor spacesPetsDecor

4.98 out of 5 average rating, 111 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

PetsOutdoor spacesAir conditioning

4.96 out of 5 average rating, 398 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

PetsOutdoor spacesHot tub

4.98 out of 5 average rating, 178 reviews

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

PetsWalkabilityFamily

Private, pet-friendly home rentals

4.99 out of 5 average rating, 159 reviews

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

WalkabilityPetsNearby

4.95 out of 5 average rating, 154 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.

Flat in Lenox

Lovely Downtown Lenox apt, walk to everything!

PetsWalkabilityCheckout

Superhost

Home in West Stockbridge

Exceptional Stockbridge Retreat

Outdoor spacesPetsBathroom

4.92 out of 5 average rating, 25 reviews

4.99 out of 5 average rating, 88 reviews

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 spacesDecor

4.94 out of 5 average rating, 18 reviews

Home in West Stockbridge

Pixley Forest | 15 Mins To Tanglewood • Fireplace

PetsOutdoor spacesHospitality

4.97 out of 5 average rating, 91 reviews

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

Outdoor spacesPetsQuiet

An outdoor area features a wooden barrel sauna alongside a modern hot tub. The hot tub's white surface contrasts with the natural wood of the sauna, set against a backdrop of lush green trees and a wooden fence, creating a serene environment for relaxation.

5.0 out of 5 average rating, 56 reviews

Sauna + Hot Tub Escape | Private & Pet Friendly

WalkabilityPetsView