Bed and breakfast holiday rentals in Pioneer Valley

Find and book unique bed & 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 favourite

Guest suite in Agawam

4.96 out of 5 average rating, 184 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

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 favourite

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 favourite

Private room in Northampton

4.95 out of 5 average rating, 778 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 favourite

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.

Cabin in Sheffield

4.77 out of 5 average rating, 71 reviews

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

Top guest favourite

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 favourite

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 favourite

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 favourite

Flat 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 favourite

Private room in Coventry

4.99 out of 5 average rating, 196 reviews

Jan's Phoenix Nest Lakefront B&B

15 minutes from the University of Connecticut on pristine Coventry Lake. Our B&B has all modern amenities. We offer a second floor bedroom and a private bath in our recently built home. Also a private sitting room and balcony overlooking the lake. Come and enjoy beautiful Coventry Lake and delicious breakfasts each morning. Food allergies? No worries, we are happy to provide wonderful gluten, egg, and/or dairy-free breakfasts. Hosted by Jan & Tom.

Top guest favourite

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.