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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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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax 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! ☺

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 suite in Richmond

4.93 out of 5 average rating, 181 reviews

Ski Bousquet/Private Ranch/Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

Cottage in Williamstown

4.89 out of 5 average rating, 179 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Rental unit in Pine Plains

4.98 out of 5 average rating, 145 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.

Cabin in West Coxsackie

5 out of 5 average rating, 39 reviews

French country cottage, fireplace & hottub

Enjoy the best of the Hudson Valley, minutes to the Hud River and Historic Reed St in the charming town of Coxsackie NY. Central locale to Hudson, Athens and Catskill. Explore the Catskills to hike/bike/kayak. Chefs kitchen, fireplace, shiplap, original wood beams and marble bathrooms showcase a cozy home. Enjoy a nice hot tub soak at night We offer two swimming hole/cold plunge areas in the creek and a MOBILE wood fired Finnish sauna for hire/rent to complete your mini health retreat.

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

Home in Hillsdale

4.91 out of 5 average rating, 114 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

Home in Albany

4.91 out of 5 average rating, 194 reviews

Modern home, King Bed 4 bed 2bath, Crib, parking

Come relax at a Hidden Gem in the heart of Albany, NY. It is centrally located between Albany Med hospitals and Saint Peters Hospital and in close proximity to the downtown college campuses of UAlbany, Saint Rose, Albany Pharmaceutical, Albany Law school and medical school, and the New York State capital. Some of the best restaurants and pubs are just minutes from this central location. It is only a 15-minute ride to the Albany International Airport.

Home in Hudson

4.74 out of 5 average rating, 315 reviews

Cute Hudson Abode- 1 Block to Warren

𝓣𝓱𝓮 𝓔𝓶𝓮𝓻𝓪𝓵𝓭 𝓢𝓾𝓲𝓽𝓮 Step back in time to the days of speakeasies and prohibition at our 1BR, 1BA apartment that mixes modern conveniences with antique pieces. It sits one block from popular Warren Street, so you can easily walk to shops and restaurants. Bring your furry friend too, as we're pet-friendly! From couples to weekenders to artists, this apartment is great for all kinds of travelers, immersing them in a piece of history.

Rental unit in Hawley

4.89 out of 5 average rating, 136 reviews

Green Acres Hawley Upper Studio (Bonus Room)

This space is a Large Studio Apartment in the Bonus Room above the Garage of a large log home overlooking Berkshire East Mountain Resort. Guests have shared access to the hot tub, outdoor tub/shower, deck, fire pit barbecue area and laundry facilities. You'll have sole access to the bonus room, deck & grill and full private bath. Space is comfy and charming, accessible from a private staircase or spiral into the main house's entrance hall.

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.

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Popular amenities for Pittsfield pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Stephentown

4.81 out of 5 average rating, 74 reviews

A Magic Spot: Booking year round.

Home in Albany

4.87 out of 5 average rating, 46 reviews

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!

Home in Shaftsbury

4.85 out of 5 average rating, 118 reviews

Quaint One-Story Vermont House with Mountain View

Home in Ghent

4.9 out of 5 average rating, 274 reviews

Renovated guesthouse on 52 acres!

Home in Ghent

4.98 out of 5 average rating, 66 reviews

Blue House

Home in Craryville

4.95 out of 5 average rating, 22 reviews

Hudson Valley Swim/Ski Lake House Rental

Home in New Marlborough

4.84 out of 5 average rating, 83 reviews

Peaceful, Post and Beam Loft, Sleeps 9

Home in Hillsdale

4.8 out of 5 average rating, 41 reviews

Charming Columbia County Farm House

Pet-friendly home rentals with a pool

Cabin in Hudson

4.88 out of 5 average rating, 8 reviews

Hudson Hill House - Sun & Fun w/ Pool near Hudson

Guesthouse in Lenox

4.92 out of 5 average rating, 193 reviews

Modern Barn with Loft at House on Golden Hill

Home in Ghent

4.88 out of 5 average rating, 301 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Farm stay in Red Hook

4.99 out of 5 average rating, 146 reviews

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Rental unit in Rexford

4.96 out of 5 average rating, 357 reviews

Need a Getaway??

Cabin in Red Hook

4.96 out of 5 average rating, 335 reviews

Modern Upstate Cabin, near Rhinebeck NY

Home in East Chatham

4.75 out of 5 average rating, 4 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

Cottage in Hudson

4.8 out of 5 average rating, 102 reviews

Stylish Spa-Cottage Escape@Hudsons ClearCreekFarm

Private, pet-friendly home rentals

Cabin in East Nassau

4.95 out of 5 average rating, 39 reviews

Cozy Country Cabin: Skiing,Hiking, fishing.

Cottage in Valatie

4.85 out of 5 average rating, 40 reviews

Hudson: MV Buren 2 bedroom cottage Lake Property

Rental unit in Wilmington

4.65 out of 5 average rating, 62 reviews

2 br apartment 12 mins to Mount Snow Unit #2

Rental unit in North Adams

4.91 out of 5 average rating, 433 reviews

Private guest apartment. One block from downtown.

Rental unit in Hudson

4.91 out of 5 average rating, 65 reviews

Cozy 2-BR Garden Apartment, Close to Warren Street

Cottage in Red Hook

4.99 out of 5 average rating, 67 reviews

Creekside Cottage | The Fitz House Red Hook NY

Home in Craryville

4.92 out of 5 average rating, 109 reviews

The Gatehouse at Raspberry Ridge

Home in North Adams

5 out of 5 average rating, 14 reviews

Gregory Art House

Quick stats about vacation rentals that are pet-friendly in Pittsfield

Total rentals
70 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Destinations to explore