Pet-friendly holiday rentals in Great Barrington

4.95 out of 5 average rating, 185 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.

WalkabilityOutdoor spacesIndoor spaces

Apartment in Great Barrington

4.93 out of 5 average rating, 175 reviews

King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires

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 KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Youtube TV with NFL Pack

Outdoor spacesPetsParking

A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.

4.94 out of 5 average rating, 144 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

Outdoor spacesPetsComfort

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, 171 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.

Outdoor spacesPetsCheckout

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.

Outdoor spacesPetsCondition

4.99 out of 5 average rating, 136 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.

WalkabilityOutdoor spacesSkiing

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, 169 reviews

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

WalkabilityOutdoor spacesBathroom

Tiny home in New Marlborough

4.94 out of 5 average rating, 187 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.

WalkabilityOutdoor spacesCleanliness

Barn in Town of Hillsdale

4.97 out of 5 average rating, 179 reviews

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.

WalkabilityOutdoor spacesPool

4.97 out of 5 average rating, 101 reviews

Cabin in East Nassau

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

Escape to your modern mountain retreat—perfect for Summer getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or Summer adventures.

PetsOutdoor spacesSleep quality

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, 126 reviews

Private Home in The Berkshires (New Hot Tub!)

Leave your worries and stress behind and enjoy all the beautiful Berkshires have to offer! This fully remodeled home is ready to serve as your new favorite vacation spot! Whether you’re looking to enjoy a laid back getaway or an adventurous stay, look no further. You’re a short 10 minute drive to Ski Butternut, less than 15 minutes to Catamount, and about 20 minutes away from Tanglewood Music Center!

PetsWalkabilityHeating

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, 139 reviews

Never too early to book for the Holidays & NYE!

My place is close to restaurants and dining, family-friendly activities, nightlife Tangelwood, Jacobs Pillow, Mahaiwe Arts Center, Arlo Guthrie Center. You’ll love my place because of the privacy, the views, the location, the ambiance, the outdoors space. My place is good for couples and families (with kids). It has new geo-thermal central heat and AC.

Outdoor spacesWalkabilityHeating

Popular amenities for Great Barrington pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 151 reviews

A newly built house is surrounded by lush greenery, featuring a spacious deck with comfortable seating. The exterior showcases a combination of blue siding and large windows, allowing natural light to flow indoors. A stone patio with seating is visible, enhancing the outdoor living experience.

Home in New Marlborough

Lake House in the Berkshire (Access Dock & Canoe

PetsOutdoor spacesQuiet

4.96 out of 5 average rating, 229 reviews

Home in Monterey

Beautiful family home, Hike, Fireplace, Sleeps 12

WalkabilityOutdoor spacesParks

4.95 out of 5 average rating, 128 reviews

Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Outdoor spacesPetsLayout

4.89 out of 5 average rating, 375 reviews

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

Home in Ghent

Modern Barn on 12 acres w Sauna, FirePit+swimming

Outdoor spacesPetsBackyard

5.0 out of 5 average rating, 112 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

Outdoor spacesWalkabilityBarbecue

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.

4.85 out of 5 average rating, 137 reviews

Great Barrington, Cabin Sleeps 14, Walk To Town

WalkabilityOutdoor spacesSkiing

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

Outdoor spacesWalkabilityAccess

4.97 out of 5 average rating, 137 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 spacesPetsKitchen

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 390 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 spacesAmenities

4.88 out of 5 average rating, 215 reviews

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

Outdoor spacesPetsSkiing

5.0 out of 5 average rating, 108 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 spacesPetsBathroom

4.96 out of 5 average rating, 129 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.

Outdoor spacesPetsKitchen

4.95 out of 5 average rating, 168 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

PetsWalkabilityHospitality

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 spacesFamily

Superhost

An aerial view captures the lakefront vacation house surrounded by greenery and calm waters. The property features a spacious lawn leading to the lake, with several vehicles parked near the house, highlighting its accessibility and serene location in the lake community.

Holiday home in Athens

4.88 out of 5 average rating, 124 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

WalkabilityPetsLayout

Superhost

Home in Becket

4.87 out of 5 average rating, 116 reviews

Berkshires Lodge | Pool, Hot Tub & Fire Pit

PetsOutdoor spacesCheck-in

Private, pet-friendly home rentals

Cabin in Litchfield County

A cozy living area features a brown leather sofa with white throw pillows, positioned beside a window that allows natural light. A wooden coffee table sits atop a blue and white woven rug, complemented by a comfortable armchair. Shelves display decorative items and fresh flowers add a welcoming touch.

4.93 out of 5 average rating, 151 reviews

Blackberry Cottage

Outdoor spacesPetsDecor

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.

WalkabilityOutdoor spacesComfort

5.0 out of 5 average rating, 103 reviews

Tiny home in Chatham

Romantic-Private-Western Tiny Cabin w/HOT TUB

WalkabilityOutdoor spacesIndoor spaces

Cabin in Town of Hillsdale

The living area features wooden beams and warm wooden flooring. A cozy gray sofa adorned with patterned cushions faces a small coffee table. A comfortable chair and a desk are included, with natural light streaming through multiple windows.

4.88 out of 5 average rating, 187 reviews

Cabin in the woods near Catamount Ski resort

PetsOutdoor spacesLaundry

5.0 out of 5 average rating, 62 reviews

A modern living area features comfortable seating arrangements with plush chairs and a sofa. The open kitchen, equipped with stainless steel appliances and a central island, is partially visible. Natural light is welcomed through large windows, enhancing the warm, inviting decor.

Loft in Great Barrington

The Nest 5 min walk to downtown Great Barrington

WalkabilityOutdoor spacesBathroom

4.98 out of 5 average rating, 43 reviews

A spacious great room showcases high wooden ceilings and exposed beams. Vintage furniture, including a green upholstered chair and a light brown armchair, surrounds a wooden coffee table. A rustic dining area is visible in the background, leading to the kitchen area with modern appliances.

Barn in New Marlborough

Hartsville Barn in the Berkshires

WalkabilityOutdoor spacesBackyard

Apartment in Great Barrington

A charming red house is framed by green trees and colorful plants in front. The home features a welcoming porch adorned with vibrant flowers, creating a harmonious blend with the surrounding natural landscape.

4.98 out of 5 average rating, 47 reviews

The River’s Whisper

WalkabilityPetsQuiet

A charming house is nestled among autumn foliage, displaying warm earthy tones. A winding stone pathway leads to the entrance, framed by a well-maintained stone wall and lush greenery. Colorful leaves adorn the surrounding trees, creating a serene and inviting landscape.