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Bed and breakfast holiday rentals in Pioneer Valley

Find and book unique bed & breakfast rentals on Airbnb

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Popular amenities for bed & breakfast rentals in Pioneer Valley

Family-friendly bed & breakfast rentals

Private room in Stafford
4.96 out of 5 average rating, 26 reviews

Brimfield Show near Innkeeper Place B&B: Heritage

ValRating, 5 stars23 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.
Top guest favourite
Private room in Hartford
4.95 out of 5 average rating, 332 reviews

Private suite in James Colt townhouse

KeyaRating, 5 starstoday
Jane and Earl are such excellent hosts! So friendly, responsive and accommodating. Their house is so easily walkable to downtown Hartford. They have great local tips in the room, which is very clean, comfortable and well-appointed. The home itself is beautiful, too!
Guest favourite
Private room in Manchester
5 out of 5 average rating, 26 reviews

Your own 2 Bedroom Guest Suite w/Full Bath

SvetlanaRating, 5 stars3 months ago
Virginia was a wonderful host! Everything was perfect - clean, cozy, and so peaceful. The place is in a quiet and pleasant area, making it a great spot to relax. A special thank you for the little breakfast each morning and the freshly brewed coffee - it was such a lovely touch! We truly enjoyed our stay and would love to come back.
Top guest favourite
Private room in Amherst
4.91 out of 5 average rating, 212 reviews

OrchardSlope

StephenRating, 5 stars1 week ago
We had a lovely and very comfortable stay at Michele’s place. They made the trip a wonderful and memorable weekend.
Top guest favourite
Private room in Williamstown
4.96 out of 5 average rating, 121 reviews

Cozy 3 bedroom cape at end of road in Williamstown

CarolineRating, 5 stars1 week ago
Great spot for our son’s graduation. We had the upstairs which gave us privacy and flexibility in case our other son and a cousin could join us. Cozy, clean and comfortable. Charmaine was a warm and gracious hostess. Good coffee in the morning.
Superhost
Private room in Northampton
4.91 out of 5 average rating, 35 reviews

Large room on private floor

NancyRating, 5 stars9 months ago
I loved my stay. Yulia was very responsive to my messages as I arrived later than expected. The space is very private with a lovely garden outside the window. The bed was super-comfy with plenty of storage space in the room. And the shower water pressure was a dream! Both hosts were very friendly and made me feel welcome right away. I would definitely stay here again. Thank you both! Nancy
Superhost
Private room in Lakeville
4.46 out of 5 average rating, 28 reviews

Queen Master Bedroom

JohnRating, 5 stars8 months ago
Terry was super nice and the place was great. She even offered to pick me up dinner and welcomed me with a beer out of her refrigerator. 10 out of 10, would recommend.
Top guest favourite
Private room in Amherst
4.93 out of 5 average rating, 208 reviews

BigSkyHilltop: Queen & single bed, full breakfast

PatriciaRating, 5 stars9 months ago
I spent a wonderful 24 hours in Josette’s home. It was one of the best Airbnbs I ever stayed in. Beautiful surroundings, an amazing breakfast and a super comfortable bed. I hope to be back.

Bed and breakfast rentals with breakfast

Private room in Great Barrington
5 out of 5 average rating, 29 reviews

Granville House - Queen traditional

DanielleRating, 5 stars25 months ago
It was an absolute delight staying at The Granville House. The hosts were friendly and responsive, the space was beautifully curated and well appointed, and the location could not have been better. The breakfast provided was super tasty (muffin masters!), and the dining room vibes were excellent — music, decor, & the overall aesthetics of this place blew my mind. You can tell Terry and Terri have worked in hospitality for a long time and put a great deal of care into making the guest experience superb. I booked our long weekend on a whim and am so lucky there was availability; I have already recommended The Granville House to several of my friends.
Private room in Goshen
4.91 out of 5 average rating, 99 reviews

Classic New England Bed & Breakfast

AngelaRating, 5 stars8 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!
Top guest favourite
Private room in Enfield
5 out of 5 average rating, 83 reviews

Antique1242, Queen Elizabeth II suite. British

DaveRating, 5 stars1 week ago
Helen’s Bed & Breakfast is exactly that and one needs look no further to be able to experience that in a quaint Connecticut town just 10 minutes drive from downtown Springfield and, I think, about 10 miles from Bradley International airport. We came to watch our son participate in an Ironman competition there, so we took both of their rentable bedrooms and had the place to ourselves. Helen was very accommodating of our need to get him out the door at 5AM and then return around Mid-day so he could grab a shower afterwards….for us it sure beat having to worry with a usual hotel/motel stay. A nice Italian restaurant in town (Sofia’s) and a country diner nearby that was open for our early morning needs…. Rooms were decorated elegantly and a common living area downstairs was full of interesting British decorations to look at!
Private room in Ashford
5 out of 5 average rating, 9 reviews

Henrietta Suite

MissRating, 5 stars28 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 stars6 months ago
Gorgeous home with an artist’s touch. Bill and Pamela are kind and thoughtful. Very much enjoyed my stay with them.
Top guest favourite
Private room in Sheffield
4.97 out of 5 average rating, 33 reviews

Beautiful Room in Hartfield House - The Berkshires

PeterRating, 5 stars7 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!
Superhost
Private room in Norfolk

C1 Carriage House at Blackberry River Inn

LindsayRating, 5 stars9 months ago
Oh....it was a great place to stay. I had my pup with me, and it worked out so well. Attended a concert down the street, and it was great to be back at the inn at a few minute's after the concert ended. Breakfast was wonderful, and the staff were so personable and accommodating . Look forward to my next visit!!
Private room in Barkhamsted
4.55 out of 5 average rating, 20 reviews

Legends BNB Lodge RM 1 $79

IanRating, 5 stars72 months ago
What a great spot. We weren’t there for the fishing, everyone else was, but we still loved the place and enjoyed the company of the other guests.

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 stars10 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 stars5 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, 106 reviews

The Lacey Rose - The Golden Room

KeithRating, 5 stars1 month ago
The Lacey Rose is an absolutely stunning Victorian home built in the early 1800’s. Every single detail of the home from the paintings and artwork on the stained glass windows, to the ornate ceilings and walls, to the beautifully curated outside space complete with a pool and several relaxing areas with chairs and tables to lounge. Denise was friendly and helpful, and made our breakfast experience absolutely flawless!!! I can’t recommend this place enough, please if you are in the are you must check it out! This is the epitome of what one expects when booking a B&B at such a fabulous location. Thank you again Denise, I’m sure I’ll be back!!
Private room in Cornwall

Cornwall Inn - Two beds (sorry, no pets)

GenyRating, 5 stars11 months ago
A very pleasant experience, we will be back!
Private room in Newfane
5 out of 5 average rating, 3 reviews

Queen bed + private bath, breakfast included

SebastianRating, 5 stars21 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!
Private room in Newfane
5 out of 5 average rating, 9 reviews

King bed+private bath, breakfast included

CarolRating, 5 stars29 months ago
I recently spent 3 snowy, quintessentially Vermont days at Thomas & Ravi’s guest house in Newfane, VT. I was given excellent directions & upon arrival Thomas helped heft my heavy ski luggage. This idyllic setting is conveniently located between Brattleboro and Mt. Snow and within a 45 minute drive to Stratton. Would most definitely recommend for a DIY retreat!
Superhost
Private room in Windsor

Graduation season is around the corner, book now!

ChristineRating, 5 stars7 months ago
Sandra and Tom are amazing hosts. Everything is so cozy and they are incredibly warm and welcoming, it was home away from home! Sandra is an amazing cook and was so accommodating to our individual preferences. Highly recommend and definitely would stay here again!!
Top guest favourite
Private room in Pittsfield
5 out of 5 average rating, 31 reviews

Petite space for a getaway

RuthRating, 5 stars1 week ago
Great place here. Josie and her husband were very friendly and it felt like home. I had a great conversation with them as well and they were kind to respond to my questions. They do also respect your privacy. I will recommend their place.

Destinations to explore