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Pet-friendly vacation rentals in Pioneer Valley

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Pioneer Valley

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

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Top guest favorite

A spacious living room features a vaulted ceiling and an arched window that allows natural light to flood the space. Comfortable seating arrangements include two red sofas and a patterned area rug. Shelving units display decorative items, while a media system is positioned above the fireplace.

Home in West Brattleboro

4.93 out of 5 average rating, 117 reviews

Modern Spacious Home with Mountain Views

Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

Top guest favorite

A wooden staircase leads to a cozy outdoor space with a grassy yard. Two small pumpkins are positioned on the steps, while trees in various fall colors create a serene backdrop. Natural stone pathways are visible, inviting exploration of the peaceful surroundings.

Guesthouse in Northampton

5 out of 5 average rating, 347 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

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! ☺

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

4.9 out of 5 average rating, 186 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!

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, 99 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.

A charming house is set within a wooded area, with autumn foliage creating a colorful backdrop. The exterior features a stone fireplace and expansive windows, offering glimpses of the serene environment. Nearby, a fire pit with seating is positioned on the green lawn.

4.93 out of 5 average rating, 114 reviews

Beautiful, quiet and cozy home in Becket!

If you are looking for a peaceful and relaxing getaway, then this is the place for you! Our cozy house in the Berkshires is ready to invite you to surround yourself with nature and see its beauty. Our home has 2 bedrooms and 1 bath, but has enough room to sleep up to 6 guests. There is also a living room, stocked kitchen and a room with a sleep sofa. Feel free to enjoy the wood burning electric fire place, the back deck, grill and fire pit outside. Pets are welcome! Book your stay & enjoy!

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, 207 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

A comfortable living area is furnished with two gray sofas adorned with decorative pillows. A wooden coffee table sits in the center, surrounded by a patterned area rug. A dining table with red chairs is positioned nearby, creating an inviting space for relaxation and gathering.

Apartment in Keene

4.94 out of 5 average rating, 218 reviews

The Carriage House Loft: Seasonal Stays

Welcome to The Phineas Handerson House, originally built in 1827 by the “the happiest man in town” Able Wilder. Modern eclectic two-bedroom(no door on loft bedroom) apartment, just one block from Central Square in Downtown Keene. Featuring newly remodeled kitchen, fitted with electric range and microwave. Other tenants occupy part of the building, but guests have a private entrance and off-street parking behind the building. Comfortable for up to four guests. Pet friendly!

An exterior view of the apartment highlights a wooden facade with large reflective windows. A patio area with picnic tables is visible alongside lush greenery and scattered leaves, emphasizing the natural surroundings. The scene is set against vibrant autumn foliage in the background.

Apartment in Northampton

4.93 out of 5 average rating, 126 reviews

Mt. View Wood-burning Fireplace

The hilltop setting offers spectacular and calming views. Spacious, uncluttered, and comfortable with floor to ceiling windows. Kitchen is well equipped and stocked. Separate dining room seats 6. Beds and bedding are high quality and bath linens are organic cotton. Large library and music provided by SONOS sound system with Napster. Wood burning fireplace. Two terraces and 3 acres of gardens. Garage. Pets welcome with advance notice. Sound proof construction.

A serene nighttime view of the log home showcases illuminated windows against a dark sky, with snow gently covering the ground. A warm glow emanates from the outdoor area, highlighting a stone fire pit. Trees are silhouetted, adding depth to the picturesque landscape.

Apartment in Hawley

4.89 out of 5 average rating, 146 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, deck, fire pit barbecue area and limited access to host's 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.

A cozy living area is visible, featuring a sofa and a coffee table, with a decorative rug underneath. A large sliding glass door opens to a wooden deck, permitting views of the surrounding nature. A dog sits patiently by the door, observing the outdoors.

Cottage in Lanesborough

4.84 out of 5 average rating, 278 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016) CURRENTLY BEING UPDATED and RENOVATED, (March and April 2025!) private cottage 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. For conditions message Jill.

A fenced backyard is visible, featuring a mix of grassy areas and trees. The Classic Lake Cabin is positioned nearby, showcasing two outdoor seating areas and a fire pit surrounded by Adirondack chairs. Lush greenery adds a natural backdrop to the outdoor space.

Cabin in Coventry

4.85 out of 5 average rating, 167 reviews

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

The Lake House boasts an outdoor patio with a dog-run, complimentary kayaks for exploration, and a cozy fire pit under the starlight sky! ● 333 Mbps Wi-Fi | 43” Smart UHD TV | Washer & Dryer ● Nintendo (NES) w/ 30 Games | Board Games | Puzzles ● 4x Kayaks | Watercraft Trolleys | Horseshoe Pit ● Patio w/ Fire Pit & Gas Grill| Full Kitchen | Coffee (Keurig) Drive to: UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Pioneer Valley pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

A dining table with four chairs is set against a wall, while a small kitchenette is visible in the background. A pair of comfortable sofas, one adorned with a decorative pillow, offers seating in the cozy living area. Natural light filters through the window, enhancing the warm ambiance.

Home in Feeding Hills

4.89 out of 5 average rating, 968 reviews

Farm Fresh Feeding Hills

Top guest favorite

Home in Northampton

4.94 out of 5 average rating, 184 reviews

Historic Williams House

The open dining area features a wooden table surrounded by six light-colored chairs. A view into the kitchen reveals modern appliances and cabinetry. Warm wood accents provide contrast against the light walls, while natural light enters through nearby windows, enhancing the inviting ambiance.

Home in Brattleboro

4.94 out of 5 average rating, 203 reviews

Frosted Willows

A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.

Home in South Windsor

4.91 out of 5 average rating, 140 reviews

Spacious 3 Bedroom Ranch With Office

A spacious living room features a dark sectional sofa facing a window adorned with blue curtains. Light hardwood floors enhance the ambiance. Colorful artwork is displayed on the walls, and a stained glass door adds character. A ceiling fan provides ventilation.

Home in Springfield

4.94 out of 5 average rating, 85 reviews

Clean/Spacious 1 bedroom house. Kitchen, LR, DR.

Top guest favorite

A snow-covered path leads to Stone n' Sky Lodge, which stands out against a winter landscape. Large trees frame the scene, with gentle snowfall creating a serene atmosphere. The lodge features a screened-in porch and is partially obscured by snowdrifts.

Home in New Salem

4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

Top guest favorite

The exterior of the farmhouse is captured, showcasing a charming white facade with a screened-in porch. Lush green trees surround the property, with a vibrant red tree providing a pop of color. A spacious grassy area is visible, leading to a wooden deck.

Home in Colebrook

4.99 out of 5 average rating, 221 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

The exterior of the house presents a charming two-story design, surrounded by a spacious yard featuring trees and blooming shrubs. A wide driveway leads to a two-car garage, while the house's yellow facade and gray roof create a welcoming appearance.

Home in Bloomfield

4.96 out of 5 average rating, 118 reviews

Spacious Charming New England Cape

Pet-friendly home rentals with a pool

Top guest favorite

A wooden deck offers a serene escape surrounded by lush greenery. Comfortable seating is provided with blue and green armchairs facing a central table. A chiminea adds a cozy touch, inviting relaxation in this peaceful outdoor setting.

Home in Wilmington

5 out of 5 average rating, 14 reviews

Spring Hiking Pet Retreat I Game RM l ChimneyHill

Home in Colrain

4.9 out of 5 average rating, 126 reviews

The 1770 House

Apartment in Burlington

4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

A charm-filled Colonial home is set amid vibrant autumn foliage. The brick exterior features classic green shutters and a welcoming porch. Solar panels are visible on the roof, contributing to the home's modern amenities. A path lined with fallen leaves leads to the entrance.

4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

A detached red barn is surrounded by a grassy yard, with patches of snow visible on the ground. The property features a gravel driveway leading to the barn's double garage doors. Mature trees line the background, offering a natural setting.

Guesthouse in Lenox

4.9 out of 5 average rating, 233 reviews

Modern Barn with Loft at House on Golden Hill

A wooden deck with two orange chairs overlooks a serene pond surrounded by vibrant autumn foliage. A small sandy area leads to a floating dock on the water, creating a peaceful spot for relaxation and enjoying nature.

Tiny home in Brattleboro

4.87 out of 5 average rating, 214 reviews

“Sugar Maple” Rustic Cabin Getaway with Fireplace

A private, heated saltwater pool is set against a backdrop of lush greenery and rolling hills. The pool's clear water reflects the blue sky and fluffy clouds. A black dog stands at the edge, observing the tranquil scene.

Home in Richmond

4.96 out of 5 average rating, 27 reviews

Escape to The Berkshires w/Pool by Evergreen Home

A cozy bungalow is partially obscured by lush greenery, with a spacious patio featuring a dining table under a large umbrella. Sunlight filters through the trees, creating a relaxed outdoor space that invites leisurely activities.

Home in Williamstown

4.89 out of 5 average rating, 217 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Private, pet-friendly home rentals

The exterior of a single-story house is depicted with a front porch and steps leading to the entrance. A chimney protrudes from the roof, and trees frame the surrounding area, creating a serene, natural setting.

4.92 out of 5 average rating, 49 reviews

Little House with Lots to Offer

A cozy living area features a stone fireplace with candles, complemented by a modern flat-screen TV mounted above it. A plush armchair provides seating, while windows invite natural light, showcasing a peaceful outdoor view. A small bookshelf holds various books.

Home in Manchester

4.91 out of 5 average rating, 44 reviews

4BR House- Central Location

A comfortable living area is highlighted by a gray sectional sofa and a wooden coffee table. A patterned area rug adorns the floor, while a tall bookshelf displays various items. Natural light enters through the window, complementing the warm color of the walls.

Home in North Adams

4.72 out of 5 average rating, 50 reviews

Large Charming Home close to MassMoca

A serene outdoor space is highlighted by a circle of teal chairs surrounding a firepit, nestled among vibrant autumn foliage. Tall trees with colorful leaves create a peaceful backdrop, framing the spacious yard that invites relaxation and connection with nature.

Apartment in Wilmington

4.65 out of 5 average rating, 62 reviews

2 br apartment 12 mins to Mount Snow Unit #2

The living area features warm wooden floors and a cozy seating arrangement, including a sofa and an armchair. Light pours through the window, illuminating a colorful area rug and a coffee table adorned with books. A pair of opened doors leads to the spacious bedroom, showcasing a bed with decorative bedding.

Apartment in North Adams

4.91 out of 5 average rating, 449 reviews

Private guest apartment. One block from downtown.

Top guest favorite

A welcoming private deck is visible, furnished with a table and four chairs under a Pergola adorned with greenery. The red exterior of the home complements the surrounding lush green lawn, while a variety of plants adds natural vibrancy.

Apartment in Coventry

5 out of 5 average rating, 101 reviews

Hide Away at Rock Farm UConn Private BnB “5 Star”

Top guest favorite

The exterior of a colonial-style home is displayed, featuring white siding and a metal roof. A paved walkway leads to the entrance, flanked by snow-covered areas. Rocking chairs are positioned on the porch, inviting relaxation in a serene winter setting.

Apartment in Newfane

4.97 out of 5 average rating, 448 reviews

Rock River Retreat: VT Oasis Pet Friendly

A spacious living area features a large L-shaped sectional sofa adorned with a cozy blanket. A wooden coffee table sits in front on a patterned area rug. Two windows allow natural light to fill the room, and a decorative mirror is mounted on the wall.

Apartment in West Hartford

4.85 out of 5 average rating, 115 reviews

West Hartford Center Apartment

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