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 serene winter view features snow-covered trees along the riverbank, creating a tranquil winter landscape. The railing of a deck is lined with undisturbed snow, and a muted sky contributes to the quiet atmosphere, emphasizing the peacefulness of the surrounding nature.

Guest suite in Agawam

4.96 out of 5 average rating, 190 reviews

The Waters Edge

Entire 1st floor, private Guest Suite in a contemporary home located on the scenic Ct River. Centrally located btwn Bstn & Htfd. 1 mile to Six Flags, 10-15 min to Suffield Academy, The Big E, Eastern States Exposition, Bradley Intnl Airport, MGM, bsktbl & volybl Hall of Fame, 30-40 min The Bushnell, 5 College Campus area. The CT River is home to beautiful wildlife. Protected lands provide a stunning backdrop to picturesque views. Rest's, museums, hiking, shopping & more. NO SMOKING PROPERTY.

Guest favorite

A serene outdoor space features a circular fire pit surrounded by four wooden chairs. The scene is illuminated by the warm glow of the fire, with a stunning sunset reflecting on the Connecticut River, framed by trees and rolling hills in the distance.

Guest suite in South Hadley

4.85 out of 5 average rating, 95 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 8 1 bathroom Covered parking Dock available Kayaking Boat rental available Paddle bikes and boards Views Fire pit Tour boat next door at Brunelle’s Marina. Patio Ice machine Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails

Top guest favorite

A hammock is set between two supports, resting on a grassy yard surrounded by lush greenery. The expansive field extends into a wooded area, under a partly cloudy sky that allows gentle sunlight to filter through.

Private room in Northampton

4.95 out of 5 average rating, 794 reviews

Warm Country Home Mins. from Town

Comfortable, clean, quiet room with a private bathroom. You have access to the living and dining room as well. We are about 10 minutes away by car from our vibrant downtown -- and yet are in a countrified part of Florence. Lovely patio, yard, and nearby conservation area with hiking trails. We love hosting and we take our hosting seriously to make our guests happy. We work hard to make our home clean. We are fully vaccinated against Covid. We and our lovely cats are hoping to meet you!

Top guest favorite

A log cabin features a welcoming porch with comfortable seating, surrounded by lush greenery. The exterior displays a blend of natural wood and modern design, with large windows inviting light into the interior. Stone landscaping adds to the cabin's charm.

Cabin in West Stockbridge

4.98 out of 5 average rating, 92 reviews

Modern Cabin near Tanglewood

Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.

Guest favorite

A rustic barn apartment features a weathered wooden exterior surrounded by lush greenery. Vibrant flowers enhance the garden area, which is bordered by logs and fencing. Large windows provide glimpses of the interior, inviting natural light into the spaces.

Apartment in Dummerston

4.92 out of 5 average rating, 412 reviews

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Guest favorite

A wooden silhouette of Massachusetts, colored light blue, features the word 'Hampshire' in a stylish font. The shape of the state is clearly outlined, emphasizing its notable geographical features.

Private room in Agawam

4.89 out of 5 average rating, 255 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.

Guest favorite

Farm stay in Southbridge

4.97 out of 5 average rating, 196 reviews

High Grass Farm (old listing)

[ To book us, please see our new listing at http://airbnb.com/h/highgrassfarm ] Get cozy in front of the fireplace and enjoy a romantic getaway in our beautiful and historic old house. One of the top 16 farm stays in New England! Our 1780's farmhouse has been completely renovated and retains its rustic country feel. Experience early American period life with only a few modern conveniences (e.g. full laundry and 5G wi-fi).

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

4.99 out of 5 average rating, 823 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!

Top guest favorite

A modern bathroom features a walk-in shower with a glass enclosure and sleek gray tiles. Adjacent to the shower, neatly folded towels are stacked on a shelf, with a decorative towel hanging on a rack. A contemporary sink completes the clean design.

Apartment in Pownal

4.94 out of 5 average rating, 199 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).

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

The exterior of a charming white farmhouse is showcased, featuring a black metal roof and a welcoming front porch. A red barn is visible on the left, complementing the scenic snowy landscape and clear blue sky in the background.

Barn in Guilford

4.99 out of 5 average rating, 126 reviews

The Carriage Barn

Situated on a 1792 Vermont Farmstead, the original Carriage Barn is a renovated 2-bedroom cottage that embraces historic building details within a comfortable and colorful design aesthetic. Located just 10 minutes outside of Brattleboro, Vermont, 45min to Mt Snow, and ~1hr to Stratton, Okemo, Bromley, and Magic Mountain.

Top guest favorite

A charming three-story house is depicted from the street, showcasing a light green exterior with white trim. A covered porch is visible at the entrance, surrounded by landscaped bushes. The surrounding area features a mix of homes and grassy spaces, set against a cloudy sky.

Apartment in Northampton

4.98 out of 5 average rating, 791 reviews

North Street Nest, sunny downtown apartment

This is an entire apartment, close to downtown. Off street parking is available, as well as on street parking. You won't need to to meet with anyone to check in. Outdoor seating on the deck is for your use only. The apartment is close to downtown. Many points downtown are within walking distance.