Bed and breakfast vacation rentals in Pioneer Valley

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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 bright bedroom is featured with a floral bedspread covering a spacious bed. A bedside lamp provides soft lighting. The en suite bathroom is visible through an open door, with a robe hanging conveniently nearby. A wooden table adds a touch of warmth to the room.

Private room in Deerfield

4.99 out of 5 average rating, 199 reviews

Queen bed suite, full breakfast, five stars

Bright room, 2nd floor queen bed, cotton sheets, own bathroom, sleep sofa, 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. (Also have a king room!)

Top guest favorite

A cozy living area features a neutral-colored sofa paired with a multi-faceted wooden coffee table. Decorative elements include a seasonal wreath on the wall and a small festive figure nearby. A sliding glass door leads to an outdoor deck area, enhancing the space's openness.

Guest suite in Agawam

4.96 out of 5 average rating, 196 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.

Top guest favorite

Private room in Pittsfield

4.98 out of 5 average rating, 435 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

A decorative sign featuring an anchor design and the text 'Luke & Ali Riverfront' is displayed prominently. The sign is octagonal and metallic, contrasting with the lush green landscape in the background.

Guest suite in South Hadley

4.85 out of 5 average rating, 104 reviews

River front guest suite

Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio 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 l

Top guest favorite

A gravel driveway leads to a spacious property surrounded by greenery. The two-story studio apartment is visible on the right, with light brown siding and a sloped roof. Mature trees provide shade, and a well-maintained lawn complements the inviting outdoor setting.

Private room in Sunderland

4.94 out of 5 average rating, 213 reviews

Private 2nd Floor Studio Apartment With a View!

Private second floor studio apartment with full bath, kitchenette, and office-ette. 3 miles to Sunderland Center, 20min to Amherst/Northampton. The view! Minimal decor, dedicated heating/cooling, dedicated entrance, ample parking. We only use unscented laundry detergent and cleaning products, as well as provide unscented soap and shampoo. Continental breakfasts included. Solar powered! But not completely off-grid as the automatic ABB categorization seems to indicate.

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, 809 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 and our lovely cats are hoping to meet you!

Guest favorite

Private room in Agawam

4.88 out of 5 average rating, 269 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

Private room in Belchertown

5 out of 5 average rating, 242 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.

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, 851 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

Private room in Amherst

4.91 out of 5 average rating, 221 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, 202 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).

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, 131 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 45 minutes to Mt. Snow (~1 hour to Stratton, Okemo, Bromley, and Magic Mountain), it’s a perfect home base for a cozy New England escape.