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

Guest suite in Agawam

4.96 out of 5 average rating, 185 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.

Superhost

A spacious living area features rustic wooden beams and flooring, complemented by a stone fireplace as a central focal point. Bookshelves line the walls, and a large window allows natural light to fill the space. Comfortable seating, including a blue couch, invites relaxation.

Private room in Sandisfield

4.92 out of 5 average rating, 137 reviews

Hospitality in the Berkshire Woods

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!

Guest favorite

A private dock extends over calm river water, featuring a boat covered by blue canvas. Surrounding greenery includes a large tree, casting shade onto the grass-covered bank. Gentle hills can be seen in the distance, creating a serene natural backdrop.

Guest suite in South Hadley

4.84 out of 5 average rating, 87 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 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, 779 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

The exterior of a modern house is visible, featuring large windows that allow ample light and offer scenic views. A wooden deck extends from the side, complemented by outdoor seating. The house is surrounded by a well-maintained lawn and mature trees in the background.

Private room in Amherst

4.93 out of 5 average rating, 207 reviews

BigSkyHilltop: Queen & single bed, full breakfast

BigSkyHilltop is located in a picturesque area 10 minutes from Amherst Center and close to 5 colleges; views for 50 miles; There are lots of hiking and cross country trails close by. If you'd prefer a little more privacy and a private bathroom, check our other Airbnb listing titled 'Private Suite and bathroom/full breakfast.' Joan and Josette have been fully vaccinated against Covid 19 to protect our guests -- we require that our guests have also been fully vaccinated before their arrival.

Top guest favorite

A spacious patio area is shown, featuring an in-ground pool surrounded by green foliage. Dining furniture, including a table with umbrellas, is arranged for outdoor seating. Sun loungers and potted plants add to the inviting atmosphere of the poolside area.

Private room in Bennington

5 out of 5 average rating, 119 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

We are located on 16 East Street in Bennington VT minutes from rt 7 and route 9 Main Street. Summer is more like a mini resort with a beautiful in-ground pool and Hot Tub. We also feature plenty of in-room USB phone plug-ins and extensions, in room TVs.. Perfect for couples or bring a child. (Extra Fees for children over 2 years. Sunning Deck or shaded patio dining or just relaxing with a good book poolside or the indoor lounge with a drink. We’ve got you covered. Many unexpected amenities.

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, 90 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.

Top guest favorite

A deck is shown overlooking a wooded area, with tall trees framing the view. The early evening sky displays soft pink hues as the sun sets in the distance. Wooden flooring and a modern railing complete the outdoor space, offering a serene atmosphere.

Private room in Deerfield

4.99 out of 5 average rating, 182 reviews

Queen bed suite, full breakfast, five stars

Bright room with queen bed, cotton sheets, en suite bathroom, sleep sofa for a third person, and deck. Private and close to where you want to be: four minutes' drive to Deerfield Academy, Eaglebrook or Bement, 17 miles to Northampton and Amherst and their colleges. We bring a breakfast to your door to start your day right - because it’s not just AirB! If you like a secluded place, you will be happy here with us and we will respect your privacy. The entrance is the only shared space.

Guest favorite

A charming barn exterior is adorned with rustic wooden siding and features a striking red door framed by flowering gardens. Lush greenery and colorful blooms enhance the entrance, leading to the inviting space within.

Apartment in Dummerston

4.92 out of 5 average rating, 403 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.

Top guest favorite

A charming sitting area features two pink armchairs with decorative cushions, positioned beside large windows adorned with lace curtains. An indoor plant adds greenery to the space, while a soft rug with floral motifs lies on the polished wooden floor.

Private room in Belchertown

4.98 out of 5 average rating, 193 reviews

Eclectic Victorian Charm

Comfort, character and charm on our second floor. Save your dates now for special occasions and the Brimfield Antique shows. Queen bed, small table, shared full bath with clawfoot tub and shower surround. Spacious room with Firestick TV, microwave, refrigerator, coffee maker. Light complimentary, self serve breakfast in main kitchen to eat in dining room or your private space. We encourage you to read our full description.

Top guest favorite

The grand foyer features a classic wooden staircase with intricate detailing and rich red carpet. Antique furnishings are positioned near a decorative fireplace, and floral wallpaper adorns the walls, creating a historical ambiance. Light illuminates the entryway, enhancing the inviting atmosphere.

Private room in Belchertown

5 out of 5 average rating, 226 reviews

The Lacey Rose - A Victorian Suite

Large private bedroom and full bath in lovely Victorian home located in the Historic District of Belchertown. Step back in time in this period home decorated with antiques and enjoy the convenience of being near the Five College Area and all that it offers. There are two other rooms available at The Lacey Rose. This beautiful home was built in 1810 as a colonial and renovated into a victorian in the late 1880's.

Top guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 814 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!