
Pet-friendly holiday 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.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

The cozy clubhouse
Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

House Above the Hollow
A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the local ski resort Berkshire East. There are many sights, country roads, trails to explore, along with many varied excellent restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Sunny Chalet Nestled in the Woods of Ashfield
Need some time to recharge surrounded by nature? Whether a group of friends, family or a wedding party - this property will suit all your needs. Access to hiking right out the door and loads of recreational activities such as skiing, swimming, biking. Our high speed WiFi and TV support streaming. Curl up on the couch and bask in the sunlight through the windows. Read a book by the fire. Gaze up at the stars and moon from the deck. Share a meal. A perfect spot for a retreat or family gathering.

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!

Serene 1-br suite on 75 acre horse property
Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

Cozy Hilltown Cottage
Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Tiny House Farm Retreat: Mountain Views, Fire pit
The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Light filled three bedroom apartment DT Florence!
Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

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 Country Retreat-Enhanced Studio Apartment
Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Forest Hideaway—Light, Privacy, Washer/Dryer
Wake up among 100-year-old trees, then drive ten minutes into Amherst for museums or sushi. Or hike out the door toward wooded trails. The apartment sits with our house on 5 acres of mature forest. With a kitchen & washer/dryer, the apartment is peaceful and practical, ideal for a weekend getaway or an extended stay, great for academics needing space for contemplation or for a couple visiting family. (Read about the steep driveway if planning a winter trip.)
Popular amenities for Pioneer Valley pet-friendly home rentals
Pet-friendly house rentals

Berkshires hideaway! Hikes & serenity near lake

Foliage Ready! Play Area, Crib, 11 Acre Farmhouse

Buckland House - A World Apart

Central Haus (Cozy Group Getaway)

Stone n' Sky Lodge

Ski at 19th c. Barn in The Berkshires

The Walnut Apartment

Brooksong, the perfect Berkshires getaway
Pet-friendly home rentals with a pool

The 1770 House

Sunset Ridge

Sweet Dreams Retreat

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Sweet cape near U Mass

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

NE Historical Mansion-pets and pet lovers welcome

Enjoy every season the Berkshires have to offer.
Private, pet-friendly home rentals

The King's Cottage

Private Studio for a Sweet Getaway!

Berkshires Cottage by Lake. Year Round Adventures.

Walk Downtown! 2BR 1B Historic Home

Cedar Wet Room w Soaking Tub

The Carriage Barn

2 BR LR 1BA Private In-Law Suite with Home Theater

Charming Riverfront Cottage
Destinations to explore
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- Rentals with a firepit Pioneer Valley
- Rentals with a patio Pioneer Valley
- Smoking-friendly rentals Pioneer Valley
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- Rentals with a hot tub Pioneer Valley
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- Family-friendly rentals Pioneer Valley
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- Rentals with breakfast Pioneer Valley
- Rentals with pools Pioneer Valley
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- Rentals with a fireplace Pioneer Valley
- Pet-friendly rentals Massachusetts
- Pet-friendly rentals United States
- Six Flags New England
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- TPC River Highlands
- Brownstone Adventure Sports Park
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Bushnell Park
- Brimfield State Forest
- Taconic State Park
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Bigelow Hollow State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bright Nights at Forest Park
- Talcott Mountain State Park
- Mount Sugarloaf State Reservation
- Butternut Ski Area and Tubing Center
- Dinosaur State Park
- Hartford Golf Club
- Mohawk Mountain Ski Area




