Bed and breakfast holiday rentals in Middlesex County

Find and book unique bed and breakfasts on Airbnb

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Popular amenities for Middlesex County bed and breakfasts

Family-Friendly Bed and Breakfasts

Guest favourite
Private room in Belmont
5 out of 5 average rating, 80 reviews

Sweet apt in Belmont 2-family on quiet street

SharonRating, 5 stars1 week ago
My husband and I found this to be a very comfortable place to stay while we were in Belmont taking care of some business and visiting friends. The neighborhood is lovely and quiet, the place was fully stocked with everything we needed, and LOTS of breakfast and snack foods were provided by Robin. She even had the gluten-free cereal that I normally eat—could she be psychic? ; ) In addition, she and her husband, Jon, were very friendly, helpful, and responsive without invading our space or privacy in any way—very available, but only when needed. I very much appreciated Robin’s very flexible refund policy as I needed to make a change to our dates a few weeks before our trip and she was very accommodating in this regard. We would definitely stay here again.
Top Guest favourite
Private room in Cambridge
4.93 out of 5 average rating, 286 reviews

West Cambridge, 1 BR in House near Harvard

BarbaraRating, 5 stars1 week ago
Caroline provides a home away from home. Everything was better than we probably expected. The accommodations were beautiful and very comfortable. But, the topping on the cake was our hostess, Caroline. She was a delight in every way.
Top Guest favourite
Private room in Shrewsbury
4.97 out of 5 average rating, 238 reviews

Bed & Breakfast with a warm Irish welcome (King 1)

LaurenRating, 5 stars5 months ago
Mary is absolutely amazing in every way! She is extremely hospitable, thoughtful, kind, helpful, and welcoming. I loved chatting with her and listening to her Irish accent through her stories from when she was in Ireland and beyond. Her house is very spacious and the bed is so comfortable. Her dog is darling too!
Guest favourite
Private room in Brookline
4.97 out of 5 average rating, 58 reviews

Queen Ann Brookline B&B M605 #2

JericaRating, 5 stars6 months ago
We absolutely loved our stay in Brookline! Grace was an amazing host, and her historic home was the perfect base for our Boston adventure. The location was fantastic, situated in a beautiful, safe neighborhood within walking distance to a variety of delicious restaurants and the public transit.
Top Guest favourite
Private room in Shrewsbury
4.96 out of 5 average rating, 201 reviews

Bed & Breakfast with a warm Irish welcome (King 2)

GailRating, 5 stars1 week ago
Mary is an outstanding host. I feel like I am with family when I stay with Mary. The home is truly a home, along with Asher, her dog, and the pleasant surroundings.
Superhost
Private room in Brookline
4.85 out of 5 average rating, 80 reviews

Queen Anne Brookline Bed and Breakfast M605 #1

GinnyRating, 5 stars6 months ago
Marie's organization actually books this home for Grace, the host. Grace runs an "old fashioned" bnb, with a friendly greeting as you arrive and a light breakfast featuring fresh breakfast breads and her homemade granola. We loved staying with Grace! We had plenty of privacy, a comfortable and quiet room, a private parking spot and key to come and go as we pleased. Her home is clean and safe. Grace is not intrusive at all, but she was gracious and helpful with any advice we needed during our stay. We picked exactly the right place for a perfect vacation.

Bed and breakfast rentals with breakfast

Guest favourite
Private room in Boston
4.97 out of 5 average rating, 70 reviews

1863 House Bed and Breakfast M307 Room 2

GlynisRating, 5 stars5 months ago
We were delighted to stay at the airbnb and had a wonderful time! We definitely plan to revisit and look forward to our next trip to Boston. The stay with our hosts made the whole experience very special.
Top Guest favourite
Private room in Dedham
4.93 out of 5 average rating, 75 reviews

Antique Victorian Farmhouse

DeborahRating, 5 stars6 months ago
Rosanne and I immediately hit it off. She has an adorable rescue dog. The home is stunning it reminded me of grand old homes I’ve stayed at that were professionally run bed and breakfast inns. The home is in an historic district. The neighborhood is charming. The bed was incredibly comfortable. The bedroom and bathroom were spacious. I really appreciated having a tub for soaking after my trail runs. I had access to all of the house and was able to do laundry. Despite having a bad neck injury and a dog who’d recently had leg surgery, Rosanne went out of her way to accommodate me. I felt so at home. I already know this area since I used to have a boyfriend in a nearby town. Dedham Square has lots of restaurants and a great old movie theater. The home is also near Legacy Place shopping center, which has the best Whole Foods anywhere. Being vegan, I’ve been to many during my business travels. I look forward to staying with Rosanne again soon.
Top Guest favourite
Private room in Newton
4.91 out of 5 average rating, 129 reviews

Historic relaxing clean home for 1- 2 adults

BethRating, 5 stars4 months ago
I really enjoyed my stay with Kate. She was warm, welcoming, and reliable. She is genuinely interested in people and our conversations were wide ranging, from gardening to art to history. I can't wait to return. Kate will always be my first choice of host in the Boston area.
Top Guest favourite
Private room in Newton
4.99 out of 5 average rating, 79 reviews

Alderwood Bed & Breakfast Single Room

MatthewRating, 5 stars6 months ago
This was a lovely, true "bed and breakfast", experience. Myra was a delightful host and I would love to come back some time.
Guest favourite
Private room in Boston
5 out of 5 average rating, 58 reviews

1863 House Bed and Breakfast M307 Room 1

LeneRating, 5 stars6 months ago
This place is one of the best AirBnB's I have ever stayed at. The room was huge and the house was so lovely and homely. Jane & Ben were extremely friendly and made me feel very welcome. They gave me lots of recommendations of things to do, what restaurants to go to and even gave me a map of the city. Marie was always extremely responsive and helpful when we were communicating. If I go to Boston again in the future, I will definitely want to stay at this place again.
Guest favourite
Private room in Boston
4.84 out of 5 average rating, 50 reviews

Rozinante - Queen, Harbor View

JeanneRating, 5 stars6 months ago
The most exceptional Air B&B we’ve ever stayed! The sailboat was docked in a beautifully, well kept marina. The few people we saw on their boats were quiet and very polite. The boat itself is well maintained and beautifully kept. We were in the heart of the historic district with sights to see and many restaurants within a short walk. And yet…as we sat on the deck with charcuterie and wine it was quiet and peaceful, exceptional! We will be back!
Guest favourite
Private room in Boston
4.91 out of 5 average rating, 65 reviews

Cozy Double Room in a quiet Boston neighborhood

MarkRating, 5 stars1 week ago
I enjoyed my stay at Natalie’s place. Not only is she a nice host, she is extremely responsive. The self check in made it easy to get in. I saw Natalie on my way out. She graciously offered me breakfast. Sadly I declined because I was in a rush to get to an appointment. I recommend her place!

Bed and breakfast rentals with a patio

Guest favourite
Private room in Carlisle
4.88 out of 5 average rating, 49 reviews

Postmodern Pastoral Suite | 25min to Cambridge

AnneRating, 5 stars1 week ago
Very nice small, cozy suite. It had everything we needed to prepare a few meals. The surrounding yard was lovely and the medium-firm mattress was incredibly comfortable.
Guest favourite
Private room in Newton
5 out of 5 average rating, 10 reviews

Cozy & Safe Room in Modern House

LucasRating, 5 stars7 months ago
Jean was very polite and nice. Her house is beautiful, clean and very well located. Thank you for the good vibe, Jean!
Guest favourite
Private room in Newton
4.88 out of 5 average rating, 40 reviews

Sunny and Spacious B&B in a Lakeside Neighborhood

Devin PatrickRating, 5 stars6 months ago
A beautiful craftsman style house near the center of Newton and a short drive to anywhere in the Boston area.
Private room in Watertown
4.67 out of 5 average rating, 33 reviews

ArArAt-Watertown MOTEL (Single room N1)

RolfRating, 5 stars1 week ago
Watertown is very easy to reach by bus number 71 or 70 which start at red line station Harvard. Even if it is a little bit outside of Boston centre it is a great choice to stay with Karapet. And you can use the busses with the 7 day Charly Card. TOP!!!
Private room in Tewksbury
4.67 out of 5 average rating, 9 reviews

From us to you

ShannonRating, 5 stars6 months ago
Flavia’s place was a great value for the location. The bed was very comfortable, the place was clean, and Flavia was kind and responsive to all our questions.
Superhost
Private room in Newton
4.82 out of 5 average rating, 85 reviews

King Room w/Kitchenette+Balcony

ScottRating, 5 stars4 weeks ago
I only needed the space for one night and wasn't able to see what was around. But Sheila's place is just as advertised! I wish I needed the space for longer, it is quite a nice spot! The room was spacious, very clean and contemporary. It is the perfect spot to stay just outside of Boston. I would love to stay here again!

Destinations to explore