Bed and breakfast vacation rentals in Pioneer Valley

Find and book unique bed and breakfast rentals on Airbnb

Top-rated bed and breakfast rentals in Pioneer Valley

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A sunlit family room features a high wooden ceiling and large windows allowing natural light to flood in. Comfortable seating is provided by a floral-patterned couch and wooden chairs. A wooden coffee table centers the space, complemented by a media unit positioned against the wall.
Private room in Northampton
4.95 out of 5 average rating, 884 reviews

Warm Country Home Minutes from Town

Comfortable, clean, quiet room and private bathroom. We are 10 minutes away from our vibrant downtown. You have access to the living and dining room, patio, yard, and nearby hiking trails. We love hosting and we take our hosting seriously to make our guests happy. Please understand that you are booking a homeshare listing, sharing some spaces with us if you choose to. Although our older home is “lived in," we work hard to make our home clean. We and our lovely cats are hoping to meet you!

Top guest favorite
Private room in Pittsfield
4.98 out of 5 average rating, 447 reviews

Large guest suite w/private bath in the Berkshires

A wonderful welcoming house in a beautiful residential neighborhood with no occupancy taxes! We are 15-25 minutes from Tanglewood, Kripalu, Mt Greylock, the Rockwell Museum, MassMoCA, skiing and hiking. Our home is centrally located to all of the fun things to do in the Berkshires. We've lived here for over 20 years and are happy to provide helpful insights for your stay. One of the reasons we love the Berkshires is that each season offers wonderfully unique experiences for any visitor.

Guest favorite
Private room in Suffield
4.92 out of 5 average rating, 107 reviews

The Lily House - Liv's Garden Room

Set in the historic district of Suffield, CT, this charming Victorian home offers a lovely place to stay as you journey through a quaint New England town. It has well appointed rooms, a beautiful wrap-around front porch and several gardens with walking paths. Just a short walk away from fine and casual dining, parks, the “Walk of Homes” as well as Suffield Academy. Our convenient location is only five miles from Bradley Int'l Airport and minutes from both Hartford CT, and Springfield MA.

Top guest favorite
Private room in Deerfield
4.99 out of 5 average rating, 185 reviews

King suite, full breakfast, 5 stars

Bright room with king bed, cotton sheets, own bathroom, sleep sofa, and a private porch. We bring a breakfast to your door to start your day right - because it’s not just AirB! Tucked away below Deerfield Ridge: four minutes' drive to Deerfield Academy, Eaglebrook, Bement, and just 17 miles to Amherst or Northampton and their colleges. If you like a secluded spot, you will be happy here with us and we will respect your privacy. The entrance is the only shared space.

Guest favorite
Private room in Agawam
4.88 out of 5 average rating, 304 reviews

Hampshire Room

Welcome! Our Hampshire Room is a comfortable private room w/ a brand new king bed, a laptop-friendly workspace, Wi-fi, and 40" flat screen. Conveniently next to bathroom. Convenient access: - MGM Casino-7 min - Bradley Airport-15 min - Eastern States Exposition, home of The Big E-5 min - Basketball Hall of Fame-8 min - Six Flags New England-10 min TWO extremely friendly cats, Tigger & Pounce will greet you and permit oodles of loving.

Top guest favorite
A spacious white house is set against a backdrop of lush greenery, complemented by a manicured lawn. A flowering tree adds a touch of color, while a lantern stands near the entrance, enhancing the welcoming atmosphere of the property.
Private room in Brimfield
4.96 out of 5 average rating, 445 reviews

New England Escape

We would love to have you stay at our home. ONLY 5 minutes from Old Sturbridge Village and the Brimfield Antique and Collectibles Show! Also, close to local breweries, tourist attractions, wedding destinations, the airports, and the 3 largest cities in MA. (one hour from both Logan International and Bradley International Airports.) Perfect for couples, singles, or business travelers.

Top guest favorite
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guesthouse in Granby
4.98 out of 5 average rating, 902 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Guest favorite
Private room in Amherst
4.91 out of 5 average rating, 240 reviews

OrchardSlope

"The best of the "feel right at home" AirBnb experiences. Loved it." Former guest of OrchardSlope "The Art of Hosting as an emerging peace practice - the art of caring for." Toke Moeller OrchardSlope is a single family home where we welcome and share with our Airbnb guests. Disclaimer: New photos taken with wide-angle lens are somewhat distorted. Thank you!

Top guest favorite
The exterior features a two-level home with a front porch adorned with seating. A vibrant garden filled with colorful flowers and greenery surrounds the entrance. Decorative elements, such as hanging planters and garden lights, complement the serene landscape.
Apartment in Pownal
4.95 out of 5 average rating, 203 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

Guest favorite
Place to stay in Ashfield
5 out of 5 average rating, 14 reviews

Norton Hill BnB

Norton Hill BnB is a traditional BnB with a host on site in the heart of scenic Ashfield; The home is spacious and ideal for group and family gatherings. Common areas include the dining room, a parlor, living room, and a porch that overlooks the yard. Please fully review 'The Space' & 'House Rules' details prior to reserving for a party, or a pet.

Top guest favorite
A bright hallway extends through the upper level, featuring exposed wood beams and soft yellow walls. Vintage framed artwork is displayed alongside a small table with fresh flowers. A doorway leads to a cozy space lined with bookshelves, inviting quiet reading moments.
Barn in Guilford
4.99 out of 5 average rating, 134 reviews

The Carriage Barn

Situated on a 1792 Vermont farmstead, the original Carriage Barn is a thoughtfully renovated 2-bedroom cottage that blends historic charm with colorful, comfortable design. Located just 10 minutes from Brattleboro and all that Southern Vermont has to offer, it’s a perfect home base for a cozy New England escape.

Guest favorite
Private room in Hadley
4.82 out of 5 average rating, 371 reviews

The 1797 House/Locke bedroom along CT River

Welcome to the Captain Locke room in the historic 1797 House (its birth year) in one of America’s oldest English settlements. We now welcome the world to our home along the Connecticut River. Close to UMass, Mount Holyoke, Amherst, Smith and Hampshire colleges, as well as Northampton & I-91.

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