Pet-friendly vacation rentals in Pittsfield

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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 Pittsfield

4.93 out of 5 average rating, 102 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?!

Top guest favorite

A red carriage house is set against a backdrop of mountains and blue skies. White Adirondack chairs circle a stone fire pit, while a picnic table and umbrella provide additional outdoor seating. Lush greenery surrounds the area, creating a serene environment.

Guesthouse in North Adams

5 out of 5 average rating, 273 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Guest favorite

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.

Home in Pittsfield

4.87 out of 5 average rating, 292 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!

Top guest favorite

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

4.88 out of 5 average rating, 186 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest favorite

A spacious kitchenette features a modern design with a vibrant red refrigerator and microwave, complemented by a wooden countertop. A comfortable gray couch is situated nearby. Natural light streams through multiple windows, illuminating the area, while colorful artwork adorns one wall.

Apartment in Great Barrington

4.89 out of 5 average rating, 107 reviews

Kitchenette|King Bed|Couch

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 *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Guest favorite

The living room features a wood stove, providing a focal point for warmth. A large sectional sofa is positioned for comfort, alongside a wooden rocking chair. Natural light filters through sheer curtains, illuminating the space, which is also equipped with air conditioning and a modern floor lamp.

Home in Lee

4.9 out of 5 average rating, 258 reviews

Cozy Berkshires Cottage

Stay in a cozy, newly remodeled Berkshires 1920's cottage! We've added bedrooms and a bathroom with a soaking tub upstairs, expanded the first floor bathroom and added a laundry room. The cottage is set back from the main road, easily accessible yet private. -Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. -Ideal for couples, adventurers, business travelers, and furry friends (pets). -Note: Stairs to the 2nd floor are steep: guests are responsible for child safety.

Guest favorite

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.

Guesthouse in Great Barrington

4.95 out of 5 average rating, 126 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.

Superhost

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

4.9 out of 5 average rating, 111 reviews

Elmwood Farmhouse

Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, to other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Bike Trail is just across the street with over 10 miles of scenic cycling. Whitney's Farm stand is a half mile North with fresh Produce and Deli . The house is spacious and welcoming with a sunny deck and porch.

Guest favorite

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

4.84 out of 5 average rating, 280 reviews

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

Guest favorite

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

4.93 out of 5 average rating, 376 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guest favorite

A colonial-style home is positioned amidst colorful autumn foliage, surrounded by well-maintained gardens. The front porch features a set of steps leading up to entry. The lawn, dotted with fallen leaves, extends towards the forest backdrop, under a clear blue sky.

Home in Pittsfield

4.98 out of 5 average rating, 125 reviews

Hidden Oasis in the Mountains by Evergreen Home

Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Guest favorite

A cozy seating area is illuminated by natural light from two windows, featuring a blue couch and an orange chair. A decorative rug with a circular pattern anchors the space, while a trunk serves as a coffee table. A plant adds a touch of greenery.

Cottage in Lanesborough

4.93 out of 5 average rating, 145 reviews

The Sail Loft

Cozy, private house from 1850, located in the heart of the Berkshires. On a quiet street across from a pond, the cottage has access to the Ashuwillticook rail trail. Relax on the private back porch, or in the large bath tub. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer. Close to several downhill and cross country ski spots, hiking trails and Tanglewood!