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Bed and breakfast vacation rentals in Pioneer Valley

Find and book unique bed and breakfasts on Airbnb

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Popular amenities for Pioneer Valley bed and breakfasts

Family-friendly bed and breakfasts

Private room in Worthington
4.97 out of 5 average rating, 120 reviews

Country Luxury in the Heart of the Berkshires

RyanRating, 5 stars11 months ago
Jim and Michelle were such welcoming and accommodating hosts. Their home is the perfect location tucked away in the countryside. Enjoying coffee and breakfast with Michelle on Sunday and their super friendly dog, Darby, was such a pleasant treat. Would love to come back more and explore the area. One thing to note, if you have Verizon you'll be off the grid here because cell service is sparse - but that's probably the best way to fully immerse yourself in the property and truly enjoy it!
Top guest favourite
Private room in Hartford
4.95 out of 5 average rating, 329 reviews

Private suite in James Colt townhouse

PhillipRating, 5 stars1 week ago
I felt like family staying with Jane and Earl, but they were never intrusive at all. Most hosts are either hands off or in your business, and they were neither, just spot on terrific hosts and people! Would definitely stay again, perfect for 1-2 people and located 10-15 minutes from anywhere in downtown you’d need to go!
Top guest favourite
Barn in Guilford
4.99 out of 5 average rating, 121 reviews

The Carriage Barn

EllenRating, 5 stars2 weeks ago
We recently enjoyed a lovely stay at The Carriage Barn in Guilford. Our host, Katherine, was very responsive to everything we might have needed during our visit: a very easy check in and out process, detailed instructions on how everything worked, items for our comfort (a gift of delicious chocolates, many fluffy towels, silky sheets, etc.), and was easily available via texting. The photos of her restored historic barn are very accurate - it's a beautifully designed renovation and is decorated with lovely art pieces, cozy furniture, and a huge library of books for your enjoyment. The tv works great and so does the WiFii. We traveled with our small dog and there is a baby gate available that easily snaps onto the staircase posts so I was not concerned about my dog's safety.. Best of all is the beautiful views of the gorgeous Vermont countryside. You'll see lovely sunsets here and spectacular sunrises. It's a great spot to truly relax.
Guest favourite
Private room in Manchester
5 out of 5 average rating, 25 reviews

Your own 2 Bedroom Guest Suite w/Full Bath

HannahRating, 5 stars7 months ago
Virginia was very welcoming! I didn’t realize when booking that the accommodations were part of the main house (the whole second floor is the guest suite space), with the kitchen space shared. This was by no means a problem and was user error on my part. That being said staying here was the closest to a true bed and breakfast experience I’ve had using Airbnb. Virginia had a nice light breakfast with fresh fruit, pastries, bagels and coffee each morning which was delightful. It was one of the cleanest Airbnbs I’ve stayed in. Highly recommend if you’re comfortable with a partially shared space. If I’m back in the area, I would stay again!
Guest favourite
Private room in Amherst
4.98 out of 5 average rating, 312 reviews

Lovely bedroom in Amherst. Close to U Mass

JoshuaRating, 5 stars2 weeks ago
Carolyn's is definitely a great host. I would recommend her to anyone.
Top guest favourite
Private room in Amherst
4.91 out of 5 average rating, 211 reviews

OrchardSlope

NancyRating, 5 stars3 weeks ago
We really enjoyed our visit and the house was welcoming, charming, very clean, and comfortable. The hosts were very friendly and flexible about our late arrival time. There was also delicious coffee for us in the morning!
Top guest favourite
Private room in Williamstown
4.96 out of 5 average rating, 119 reviews

Cozy 3 bedroom cape at end of road in Williamstown

JenelleRating, 5 stars2 months ago
Super charming home and guest space upstairs. We were looking for a comfy place to spend a few winter days with our Williams student and this fit the bill perfectly. Super close to campus, but the view out of the northwest window made it feel like we were in a wood cabin in the middle of the woods somewhere. Great communication with owner.
Superhost
Private room in Northampton
4.91 out of 5 average rating, 34 reviews

Large room on private floor

BillRating, 5 stars10 months ago
Our plane was delayed several times and our arrival time of 5pm was pushed back to midnight. There was no lockbox so Olena wanted a face-to-face check-in and waited up till that ungodly hour. Her lovely, well-appointed house is right next to a dense woods and no other houses are visible from Olena's. As a result we experienced complete, total silence during the sleeping hours. Although others lived in the house on the floors above ours (basement), we rarely heard or saw them and felt we had an apartment all to ourselves even though we entered through the main door. Our bedroom was the largest I've had in an AirBnB and had copious storage and furniture: closet, drawers, two chairs, desk, etc. The bed size is double (not Queen) and is actually a futon but, nonetheless, was quite comfortable. We were often greeted upon entering by Olena's large and friendly dog. We hope that her place is free during our next Northampton visit.

Bed and breakfast rentals with breakfast

Private room in Goshen
4.91 out of 5 average rating, 99 reviews

Classic New England Bed & Breakfast

AngelaRating, 5 stars6 months ago
Mary’s place is a charming little colonial farmhouse built in the late 1700s out in a beautiful rural part of CT. It is quirky and filled with signs of an earlier time while updated with modern conveniences. It’s not all shiny and new, so if that’s your thing, stay home. But if you want to be charmed with glimpses into the past, be surrounded by gorgeous countryside with parks galore and hiking at every level, and have an imagination that finds inspiration in glimpses of history, then this is your place!
Private room in New Marlborough
5 out of 5 average rating, 9 reviews

The Inn at Freeman Elms Farm B&B- Effie's Room

AndreRating, 5 stars31 months ago
Anita is a stellar host! The rooms and food were both great!
Private room in Stafford
4.96 out of 5 average rating, 26 reviews

Brimfield Show near Innkeeper Place B&B: Heritage

ValRating, 5 stars21 months ago
We enjoyed our stay at the Inn. We stayed in the Heritage Room which was on the top floor. The bathroom was beautiful, the room was very clean. We loved all the personal touches around the room. Chris was very hospitable and we enjoyed chatting with him and the other guests the next morning at the breakfast table-which Chris cooked and it was excellent. Unfortunately Danele was away for the weekend and we did not get to meet her. but there’s always a next time.
Private room in Wilmington
5 out of 5 average rating, 5 reviews

Apple Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

DonRating, 5 stars34 months ago
The Wilmington Inn is always a favorite place to stay! It's always quiet and so convenient to restaurants and the shops--we'll be back!
Private room in Ashford
5 out of 5 average rating, 9 reviews

Henrietta Suite

MissRating, 5 stars27 months ago
Our favorite place to stay in CT! My husband I love that the hosts are very welcoming, they make you feel right at home, and their homemade breakfast with local ingredients is SO delicious. I'm not a huge coffee drinker but I will always have a cup of coffee Jasmine makes for us. We stayed in the same room a few years ago, and made sure to stay in the same house/room this time around again. It's so peaceful, scenic, and good vibes all around. Can't wait to visit again, and hopefully next time it'll be for a longer stay!
Top guest favourite
Private room in Norfolk
4.98 out of 5 average rating, 41 reviews

Maple House, Birch Room

StaceyRating, 5 stars5 months ago
Gorgeous home with an artist’s touch. Bill and Pamela are kind and thoughtful. Very much enjoyed my stay with them.
Guest favourite
Private room in Sheffield
4.97 out of 5 average rating, 32 reviews

Beautiful Room in Hartfield House - The Berkshires

PeterRating, 5 stars5 months ago
We had such a wonderful stay! The house is historic, beautiful, and impeccably clean. Breakfast was delicious, with French press coffee and steeped tea that we loved. Missy the dog is a joy to be around and kept our dog entertained in the massive outdoor space. We truly felt at home, and the place felt very private. There’s so much to do in the area—great hikes, antique stores, and plenty of restaurants to explore. All in all, it was a very relaxing weekend getaway from the hustle and bustle of the city. We’d love to come back!
Guest favourite
Private room in Sunderland
4.94 out of 5 average rating, 197 reviews

Private 2nd Floor Studio Apartment With a View!

PhillipRating, 5 stars4 months ago
I can’t say enough about the beauty and isolation of this spot. Within a 10 minute drive there are a variety of good restaurants and shops, and Northampton isn’t far. But for walks in the woods, biking or looking at the mountains through the 270 degree window panorama, this spot is extraordinarily spacious and cozy. There are a number of famous rock climbing sites nearby. The bathtub is the largest I’ve used, not a jacuzzi, but bigger than most hotel jacuzzis. Plenty of hot water.

Bed and breakfast rentals with a patio

Guest favourite
Private room in Litchfield County
4.92 out of 5 average rating, 12 reviews

Private en-suite Bedroom in Historic Inn

KarleneRating, 5 stars8 months ago
We totally loved our stay! The town of Norfolk is so quaint. But Airbnb bed-and-breakfast, we felt right at home really loved the breakfast in the morning when we all sat around the table and had conversations with all the guests that were staying. I would definitely stay there if we return to the area.
Guest favourite
Private room in Brattleboro
5 out of 5 average rating, 9 reviews

Purple Chef's cozy lair

JackieRating, 5 stars3 months ago
What a lovely and beautiful location amongst the woods... perfect living space, a wonderful kitchen with everything we could want or need. Sharon is the consummate host. We absolutely love being there and our 2 dogs do too! We can't wait for our next visit!!
Top guest favourite
Private room in Belchertown
4.98 out of 5 average rating, 102 reviews

The Lacey Rose - The Golden Room

StevenRating, 5 stars2 weeks ago
I’ve stayed at this spot Before, and it continues to be a great location, proximate to all the places I need to visit in the area. The house is gorgeous, and it’s kept immaculate. Denise is a super host!!
Private room in Newfane
5 out of 5 average rating, 3 reviews

Queen bed + private bath, breakfast included

SebastianRating, 5 stars20 months ago
This is an idyllic setting for a beautiful home with super friendly and caring hosts. The large house, a retreat center with facilities for large groups, sits on a lake overlooked by a gorgeous modern treehouse. Tom and Ravi are excellent hosts and I enjoyed chatting and eating with them and learning about their vision for the property, communal and artistic, with nourishing food fresh from local farms, and a mix of interesting guests. This is the kind of place where you can truly unwind in natural green, wander the extensive grounds and connect socially if that suits you. The beds are comfortable, each room with its own bathroom, and the living rooms are spacious and with walls of books and artwork. Cannot recommend this place more highly. If you’re lucky enough to find availability, don’t hesitate!
Top guest favourite
Private room in Guilford
5 out of 5 average rating, 8 reviews

Welcoming B&B room with balcony and whirlpool bath

KevinRating, 5 stars13 months ago
Great hidden gem It is a beautiful location, next to the river, peaceful with a waterfall, covered bridge, and great food. Assume surprised

Destinations to explore