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

Home in Saugerties

4.97 out of 5 average rating, 123 reviews

Welcome to Malden Manor, in a prime location!

Prime Location! Recently remodeled 2-story home, 3-bedrooms, 2-bath. Walking distance to HITS & just minutes to Village of Saugerties & NYS Thruway. Pet-friendly, high speed internet, & pack-play/highchair ready. Explore equestrian shows at HITS, hiking in the Catskill mountains, Lighthouse visits, Sawyer Motors Car show, Esopus Creek kayaking, and Hunter Mountain Ski Resort, 15-min drive. Or enjoy staying home in backyard grilling near the outdoor fire pit, & entertaining with family & friends

Superhost

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Guest favorite

Cottage in Averill Park

4.95 out of 5 average rating, 131 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.

Guest favorite

Rental unit in Pine Plains

4.98 out of 5 average rating, 146 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.

Superhost

Cabin in Catskill

4.9 out of 5 average rating, 117 reviews

Postcard Cabins Eastern Catskills - New York

An easy drive from the city, Postcard Cabins, formerly Getaway, is the ultimate way to experience the great outdoors. Nestled across acres of private woodlands, our tiny cabins have everything you need (AC/Heat, en-suite bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you disconnect from the everyday. As part of your stay, you'll receive a complimentary allocation of provisions, like s’mores, coffee and more.*

Guest favorite

Home in Germantown

4.96 out of 5 average rating, 297 reviews

Modern Country Cottage, 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 appliances. Total privacy, high ceilings, hand plastered walls, antique wood doors. Glass doors open onto 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! For more photos at @martinasplaces at insta/gram

Guest favorite

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.

Guest favorite

Guest suite in Charlemont

4.9 out of 5 average rating, 198 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

Guest favorite

Home in Hillsdale

4.91 out of 5 average rating, 116 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

Farm stay in Coeymans Hollow

4.85 out of 5 average rating, 119 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.

Superhost

Tiny home in Nassau

4.94 out of 5 average rating, 141 reviews

Tiny Home 2 hrs NYC and BOS Lakefront WIFI

Extended stays are welcome! *** IMPORTANT *** Our photos previously showed screens enclosing the porch, but we have removed them due to wear from pets. Maintaining a pet-friendly environment is important to us, so the screens are no longer part of the tiny house. Enjoy a stay in our clean, charming, unique tiny home. This waterfront property features a private peninsula with a sandy entrance to the water.

Guest favorite

Home in Saugerties

4.99 out of 5 average rating, 139 reviews

Saugerties Village Retreat

Charming Village home located 5 minutes from Hits. Walking distance to village restaurants & shopping. Front porch, Private backyard with deck and patio. Large eat in kitchen with separate dining room. Spacious Living room with 2 couches and daybed. Cable TV & Wifi Driveway & street parking for up to 3 cars. washer, dryer, dishwasher . Fully fenced in yard for up to 2 dogs with pre approval from host.