Pet-friendly vacation rentals in Pittsfield

An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.

4.93 out of 5 average rating, 133 reviews

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

WalkabilityPetsAccess

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.

PetsOutdoor spacesBathroom

A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.

4.87 out of 5 average rating, 327 reviews

Dancing Horse Lodge

Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!

Outdoor spacesWalkabilityLaundry

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

PetsWalkabilityAir conditioning

4.93 out of 5 average rating, 207 reviews

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!

WalkabilityOutdoor spacesNearby

A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.

4.97 out of 5 average rating, 155 reviews

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

PetsOutdoor spacesHot tub

4.85 out of 5 average rating, 297 reviews

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

Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

WalkabilityOutdoor spacesFamily

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 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 spacesBathroom

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.

4.92 out of 5 average rating, 106 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Outdoor spacesPetsWifi

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.

Outdoor spacesPetsView

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.

WalkabilityPetsIndoor spaces

Popular amenities for Pittsfield pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.83 out of 5 average rating, 296 reviews

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 spacesBiking

4.9 out of 5 average rating, 122 reviews

The exterior of a renovated antique farmhouse is displayed, featuring a white facade and multiple entrances framed by greenery. A spacious lawn surrounds the house, complemented by mature trees in the background under a clear blue sky.

Home in Lanesborough

Elmwood Farmhouse

Outdoor spacesWalkabilityShared spaces

4.92 out of 5 average rating, 228 reviews

The exterior of the farmhouse is shown, highlighting its white siding and traditional architecture. Lush green lawns surround the structure, while flower beds with colorful blooms add vibrancy. Mature trees provide shade against the clear blue sky, enhancing the serene rural setting.

Home in New Ashford

Rosecroft, Historic Home, Greylock Valley Estate

WalkabilityPetsValue

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

PetsOutdoor spacesGetting around

4.97 out of 5 average rating, 225 reviews

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

PetsOutdoor spacesAccuracy

Superhost

A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.

Home in Cheshire

4.86 out of 5 average rating, 227 reviews

19th c. Barn in The Berkshires

PetsOutdoor spacesKitchen

4.86 out of 5 average rating, 118 reviews

A charming exterior view of the home shows a modest structure with a gray shingle facade and green windows. A wooden deck extends toward a seating area, while a pathway of stepping stones leads through the yard. Lush greenery is visible in the background.

Home in Clarksburg

New & Cozy~Near MoCa~Deck~River

WalkabilityOutdoor spacesHospitality

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 spacesPetsLong stay

Pet-friendly home rentals with a pool

4.83 out of 5 average rating, 106 reviews

A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.

Townhouse in Hancock

Beautiful Jiminy Peak Townhome Family Friendly

Outdoor spacesPetsCleanliness

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

Outdoor spacesPetsLayout

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.

Vacation home in Athens

4.87 out of 5 average rating, 125 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

WalkabilityOutdoor spacesAccuracy

Cottage in West Sand Lake

4.99 out of 5 average rating, 127 reviews

Cozy Cottage with pool and walk to lake

WalkabilityPetsTV

4.95 out of 5 average rating, 167 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

Outdoor spacesPetsAir conditioning

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

WalkabilityOutdoor spacesAmenities

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

Outdoor spacesWalkabilityCleanliness

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.

WalkabilityOutdoor spacesValue

Private, pet-friendly home rentals

4.89 out of 5 average rating, 208 reviews

A charming blue cottage with a wooden fence is showcased, featuring an American flag mounted on the front. The entrance includes a door framed by two windows, and a rustic fence leads to the path, surrounded by autumn leaves and forest greenery.

Cottage in Williamstown

Cute Cozy Comfy Cottage in the Berkshires

PetsWalkabilityAccuracy

Cottage in Great Barrington

The rustic carriage house is surrounded by lush greenery, featuring a vibrant garden with various plants and flowers. A teal umbrella provides shade over an outdoor seating area, complemented by a stone pathway leading to the entrance, enhancing the inviting atmosphere of the setting.

4.93 out of 5 average rating, 154 reviews

Carriage house with Chef's Kitchen, close to town

Outdoor spacesPetsKitchen

4.93 out of 5 average rating, 126 reviews

A two-story lodge is nestled among tall trees, with a babbling brook flowing in the foreground. The exterior is a rich brown wood, complemented by green foliage and rocks near the water. A small balcony is visible on the second floor, enhancing the picturesque setting.

Cottage in Austerlitz

Harvey Mountain Lodge by State Forest

Outdoor spacesPetsLong stay

4.9 out of 5 average rating, 228 reviews

A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.

Apartment in Petersburgh

The Beer Diviner Brewery Apartment

Outdoor spacesWalkabilityCheckout

4.86 out of 5 average rating, 125 reviews

A historic Victorian home is presented with multiple levels and large, decorative windows. The white exterior is complemented by a wraparound porch adorned with railings. Lush greenery surrounds the house, enhancing the inviting front entrance, while flowering shrubs add a touch of color to the landscape.

Guest suite in Adams

Quaint Suite in Center of Adams

Outdoor spacesWalkabilityNearby

4.93 out of 5 average rating, 308 reviews

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

PetsOutdoor spacesCheck-in

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

WalkabilityOutdoor spacesAmenities