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Pet-friendly holiday rentals in Western Massachusetts

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Top-rated pet-friendly home rentals in Western Massachusetts

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

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Guest favourite
Cabin in Colebrook

Rustic Pond Cabin: Nature, woodstove & deep porch

🦉Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. All natural pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay n walk the trail around the pond, have campfires outside in firepit! Clean & no crazy rules! Surrounded by acres nature! Private-Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!🦉

Outdoor spacesPetsCondition

4.95 out of 5 average rating, 130 reviews
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!

Outdoor spacesPetsAccuracy

4.99 out of 5 average rating, 159 reviews
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.

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 spacesWalkabilityHiking

4.95 out of 5 average rating, 320 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 spacesKitchen

4.97 out of 5 average rating, 110 reviews
Top guest favourite
Guest house in Cummington

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Outdoor spacesWalkabilityWifi

4.99 out of 5 average rating, 222 reviews
Top guest favourite
An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.
Home in Dalton

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

WalkabilityPetsBack garden

4.93 out of 5 average rating, 212 reviews
Top guest favourite
A panoramic view of the expansive farmland stretches towards a distant mountain range under a colorful twilight sky. Two wooden chairs are positioned on the grassy area, providing a serene spot to enjoy the landscape.
Tiny home in Northampton

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Outdoor spacesPetsBiking

4.98 out of 5 average rating, 310 reviews
Top guest favourite
A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.
Flat in Northampton

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

PetsWalkabilityAir conditioning

4.97 out of 5 average rating, 498 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

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Outdoor spacesWalkabilityBack garden

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

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Naumkeag Pumpkin Show/Christmas Lights -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

WalkabilityOutdoor spacesBeach

4.93 out of 5 average rating, 136 reviews
Top guest favourite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Flat in Conway

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Outdoor spacesWalkabilitySolo travel

4.96 out of 5 average rating, 228 reviews
Guest favourite
Tiny home in New Marlborough

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.

PetsWalkabilityView

4.94 out of 5 average rating, 201 reviews

Popular amenities for Western Massachusetts pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favourite
The farmhouse kitchen features exposed wooden beams and a large dining table surrounded by chairs. A refrigerator stands against the wall, and shelves display dishware and utensils. Natural light enters through the window and door, enhancing the spacious feel of the room.
Home in Northampton

Historic Williams House

Outdoor spacesWalkabilityAccuracy

4.94 out of 5 average rating, 213 reviews
Top guest favourite
A well-maintained home is situated on a gentle slope, featuring a neatly landscaped front yard with flowering plants and shrubs. An American flag is displayed by the entrance, and a gravel driveway leads to the garage below, surrounded by lush greenery.
Home in Amherst

The Suprenant House

WalkabilityOutdoor spacesBathroom

5.0 out of 5 average rating, 185 reviews
Top guest favourite
A view from above displays a cozy sitting area beneath exposed wooden beams. A rich, patterned rug covers the floor, while a plush armchair and a small table are positioned nearby. Natural light filters in through the adjacent windows, illuminating bookshelves filled with items.
Home in New Salem

Stone n' Sky Lodge

PetsOutdoor spacesCheck-in

4.91 out of 5 average rating, 255 reviews
Top guest favourite
Home in Monterey

Beautiful family home, Hike, Fireplace, Sleeps 12

PetsWalkabilityParks

4.96 out of 5 average rating, 237 reviews
Top guest favourite
A charming red farmhouse is set against a backdrop of rolling hills and blue skies. The property includes a separate red building nearby, surrounded by lush green grass and a landscaped stone garden featuring colorful flowers and greenery.
Home in Colrain

Secluded Farmhouse Retreat - stunning views

Outdoor spacesWalkabilityValue

4.94 out of 5 average rating, 199 reviews
Top guest favourite
A vintage red telephone rests atop a colorful magazine, featuring a circular design. The magazine's vibrant cover displays a stylized illustration of a woman, adding a nostalgic and artistic touch to the scene.
Home in North Adams

Brooklyn Zoo: Unique retreat in the Berkshires

WalkabilityPetsHiking

4.94 out of 5 average rating, 285 reviews
Guest favourite
A striking black chalet with a stone chimney is framed by snow-covered trees. The spacious deck features multiple outdoor seating areas, offering views of the surrounding winter landscape, while large windows provide ample natural light to the interior.
Home in Becket

Lakefront Retreat | Dock, Kayaks & Fire Pit

Outdoor spacesWalkabilityBeach

4.94 out of 5 average rating, 110 reviews
Guest favourite
The entrance features a covered porch with white railings, providing a welcoming pathway to the door. A potted plant with pink flowers is situated near the base of the stairs, adding a touch of greenery to the inviting entrance.
Home in Northampton

The Walnut Apartment

WalkabilityPetsAccess

4.91 out of 5 average rating, 114 reviews

Pet-friendly home rentals with a pool

Guest favourite
A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.
Flat in Holyoke

NE Historical Mansion-pets and pet lovers welcome

WalkabilityPetsPool

4.81 out of 5 average rating, 323 reviews
Guest favourite
Home in Colrain

The 1770 House

PetsWalkabilityKitchen

4.9 out of 5 average rating, 144 reviews
Top guest favourite
Barn in Town of Hillsdale

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

PetsWalkabilityView

4.97 out of 5 average rating, 185 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

Outdoor spacesPetsBack garden

4.93 out of 5 average rating, 109 reviews
Top guest favourite
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.
Flat in Otis

Enjoy every season the Berkshires have to offer.

Outdoor spacesPetsGetting around

4.96 out of 5 average rating, 134 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

WalkabilityOutdoor spacesHot tub

4.88 out of 5 average rating, 222 reviews
Top guest favourite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

WalkabilityPetsWifi

4.9 out of 5 average rating, 242 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 spacesLocation

4.98 out of 5 average rating, 136 reviews

Private, pet-friendly home rentals

Top guest favourite
A chalet-style home is situated on a forested property, with a spacious deck extending from the front. Large windows reflect the surrounding greenery, showcasing a modern aesthetic against a backdrop of autumn foliage. Rock formations and scattered leaves cover the ground.
Chalet in Peru

Swiss Chalet Style Timberframe Home in Berkshires

WalkabilityOutdoor spacesBathroom

4.93 out of 5 average rating, 311 reviews
Top guest favourite
The entrance features a white door with a windowpane design, framed by light blue siding. A decorative lantern hangs beside the door. A small potted plant rests on a blue chair, while a welcome mat adorned with black dogs is placed at the threshold.
Guest house in Northampton

Mill River Cottage (pet friendly!)

Outdoor spacesWalkabilitySleep quality

4.99 out of 5 average rating, 445 reviews
Guest favourite
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.
Treehouse in New Marlborough

Berkshire Treehouse Retreat

WalkabilityOutdoor spacesFamily

4.91 out of 5 average rating, 181 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

Outdoor spacesPetsGrill

4.96 out of 5 average rating, 114 reviews
Top guest favourite
A dining area features a wooden table surrounded by six chairs, complemented by a vibrant fruit bowl at the center. A bookshelf filled with various books stands nearby, while a wooden cabinet adds warmth to the room. Bright natural light filters through the windows.
Flat in Northampton

Charming retro retreat with vintage soaking tub

Outdoor spacesWalkabilityAir conditioning

5.0 out of 5 average rating, 157 reviews
Top guest favourite
A modern A-frame cabin is positioned among vibrant autumn foliage. The exterior features large triangular windows framed by wood, and a spacious deck surrounds the front. A stacked log wall is visible beneath the deck, creating a natural aesthetic against the landscape.
Cabin in Saugerties

Stunning 2-Bedroom A-Frame in the Woods with Sauna

PetsWalkabilityLocation

4.98 out of 5 average rating, 299 reviews
Top guest favourite
Guest suite in Belchertown

Serene 1-br suite on 75 acre horse property

WalkabilityPetsGetting around

4.98 out of 5 average rating, 174 reviews
Guest favourite
A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.
Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

PetsWalkabilityNearby

4.85 out of 5 average rating, 301 reviews

Destinations to explore