Pet-friendly vacation rentals in Pittsfield

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Pittsfield

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

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Guest favorite

A cozy cottage is surrounded by lush greenery, featuring a well-manicured lawn and colorful flower beds. A stone structure with a roof is positioned in the foreground. The cottage showcases a welcoming porch with seating and a white door, under a partly cloudy blue sky.

Cottage in Averill Park

4.95 out of 5 average rating, 136 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Top guest favorite

Home in Ballston Spa

4.94 out of 5 average rating, 109 reviews

Time to Relax, close to Saratoga.

Vacation and relax in this close to everything home with many extra touches moments away from Saratoga! Enjoy world class concerts at SPAC Visit the State Park, Adirondack hiking, taste the mineral springs and enjoy a mineral bath and massage. Place your bets at world renowned Saratoga Race Track then visit Saratoga Lake, and Lake George where you can rent boats and jet skis. Enjoy many diverse restaurants, Outlet shopping, vibrant night life, amusement park, water park, and so much more!

Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

Beautiful Vermont! (Pet Friendly)

Our home is nestled in the Green mtns, with quick access to the road. A babbling brook lulls you from the master bedroom, a clawfoot soaking tub, stocked house(this is our home we Airbnb when we're away working ).Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. Great location! PEACEFUL & PERFECT Vermont getaway! ☺

Top guest favorite

The kitchen features modern white cabinetry with black handles, complemented by a light-colored countertop. A stainless steel sink is positioned under a wall-mounted faucet. A tile backsplash in neutral tones adds texture, while a fire extinguisher is mounted for safety.

Apartment in Pine Plains

4.98 out of 5 average rating, 167 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Guest favorite

A cozy bedroom is presented with a spacious bed adorned with a white quilt and decorative pillows. A large window offers a serene view of Sadawga Lake, complemented by a window seat nearby. Light wooden cabinetry and overhead lights add warmth to the setting.

Tiny home in Whitingham

4.91 out of 5 average rating, 98 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Guest favorite

A spacious covered porch is furnished with a variety of seating options, including rocking chairs and cushioned lounge chairs. A central table is surrounded by decorative rugs, while string lights hang overhead, illuminating the area. Lush greenery is visible in the background, enhancing the outdoor experience.

Home in Saugerties

4.9 out of 5 average rating, 113 reviews

Charm and lots of space in a peaceful village

Our beloved house is located in a hamlet one mile north of Saugerties near the Hudson River. Its five bedrooms can comfortably house 9 guests, and dogs are welcome. It has a Large kitchen, very spacious living and dining rooms, a wood stove usable as a fireplace , excellent Wifi ( up to 400 mbps), AC and central heating. Our huge back porch opens on a one acre garden. All this within walking distance to the HITS championships and a 30 minutes drive to the ski slopes of Hunter.

Top guest favorite

Chalet in Dover

4.98 out of 5 average rating, 109 reviews

Mountain Chalet: Brook-Hot Tub-Firepit-Mins to Ski

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best cuisine VT has to offer.

Superhost

A spacious bedroom features a light grey bed with simple bedding. A colorful wall art piece adds character to one side, while a desk and chair occupy the other. Natural light filters through the large window, and warm wood flooring complements the overall design.

Vacation home in Hudson

4.85 out of 5 average rating, 128 reviews

Bright and Airy 2 blocks from Warren ST eb

Experience comfort and convenience in this Hudson apartment, perfect for solo travelers, couples, or small families. Enjoy the cozy ambiance of this space, complete with a fully equipped kitchen, and organic washing and cleaning products. You'll find comfortable sleeping arrangements, as well as Smart TV and board/card games for your entertainment. Unwind on your private patio. Whether you're here for business or leisure, don't miss out on this spacious, bright, peaceful space.

Guest favorite

The image displays a charming red cottage with a welcoming porch, surrounded by a well-maintained lawn and vibrant flowering bushes. A paved driveway leads to the entrance, framed by lush greenery and trees in the background, contributing to a serene, natural environment.

Guest suite in Charlemont

4.91 out of 5 average rating, 206 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Superhost

A single-story house is set on a grassy lot, featuring a sloped roof and multiple large windows. A driveway leads to a garage, while low shrubs border the front. A clear sky is visible above, with scattered clouds adding dimension.

Home in Hillsdale

4.89 out of 5 average rating, 139 reviews

Fenced yard, playroom & the Berkshires - $0 fees

Enjoy our 8.5 acre, private home. It's a great place to either relax, or enjoy nature whether it's skiing, hiking, kayaking, or biking. Ample space for numerous groups, including an enclosed backyard with grill and fire pit. 4 bedrooms and 3 baths For hikers, Taconic State Park :06 For bikers, Harlem Vally Rail Trail :08 For skiers, Catamount :05 ~2.5 hours from NYC and Boston ~ 15 min to Great Barrington, MA ~25 min to Hudson, NY ~20 min to Millerton, NY

Guest favorite

A traditional wood-burning stove is positioned against a stone fireplace, providing a rustic focal point in the living area. A laundry area is visible in the background, while a red couch adds a touch of color to the space. Natural light enhances the inviting atmosphere.

Farm stay in Coeymans Hollow

4.85 out of 5 average rating, 122 reviews

Magic Forest Farm’s Purple Palace

Our slice of paradise consists of 225 acres of forested land nestled in the foothills of the Catskills near Albany. We are a homestead and small community devoted to the principles of organic farming and self reliance. We grow much of our own food and forage many types of wild mushrooms. You will be sure to enjoy the spectacular mountain views, friendly farm animals, and secluded trails. The house is spacious and decorated with landscape oil paintings.

Guest favorite

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

4.97 out of 5 average rating, 326 reviews

Fantastic Cottage/Insane Views/Trails/Fireplace!

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!