Holiday rentals with breakfast in Middlesex County

Find and book unique Holiday Accommodation with Breakfast on Airbnb

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Popular amenities for Middlesex County Holiday Accommodation with Breakfast

Holiday House Rentals with breakfast

Top Guest favourite
Private room in Wellesley
4.99 out of 5 average rating, 189 reviews

The 1850 Morse Home with award-winning updates

LauriRating, 5 stars6 days ago
Our stay at Marilyn's was great. She was so hospitable and helpful. The home was beautiful and we especially liked the backyard and the living room. It was close to all the things that we wanted to do and it was easy to come and go. Marilyn made sure had everything we needed including returning an item that we accidentally left behind. We loved the dog Lily and she definitely added to our stay with her playfulness and energy.
Home in Randolph
4.43 out of 5 average rating, 7 reviews

Comfortable and Convenient 3 Bed Home

JahnayaRating, 5 stars1 week ago
This was a pleasant stay. My family and I enjoyed our stay. Everything was beautiful, clean and comfy.
Guest favourite
Home in Dedham
4.93 out of 5 average rating, 107 reviews

Cozy house close to Boston

RebeccaRating, 5 stars4 months ago
Karen’s home truly is cozy. We were here two weeks before Christmas and it was decorated and beautiful. Beds are comfortable, the kitchen was clean and well stocked, nice big fluffy towels and I loved the shower! We have stayed in several,places in the Boston area and this is one of the best. Even my dogs loved it!
Guest favourite
Private room in Lexington
4.94 out of 5 average rating, 109 reviews

2 rooms and private bath in Historic Lexington!

LynnRating, 5 stars6 months ago
Let me start with this: THESE HOSTS MAKE THEIR OWN MAPLE SYRUP. As if that weren’t enough, they were warm and welcoming, making me comfortable in their home from moment one. The space was cozy and exactly what I needed—and walking distance from beautiful wooded conservation land. And Deborah’s breakfast—and conversation—were truly a delicious, sweet, and savory way to start the day. I hope to be back!
Guest favourite
Private room in Billerica
4.85 out of 5 average rating, 353 reviews

Bedroom and sitting room in Lakeside Home

KevinRating, 5 stars2 weeks ago
My wife and I decided to stay in the area for a quick trip. Carol was extremely proactive and communicated with us every step of the way . She was also extremely flexible regarding our check in time . The house was beautiful and extremely clean . We had full privacy as well! We will definitely stay again !
Top Guest favourite
Private room in Boston
4.96 out of 5 average rating, 417 reviews

219 on the Ocean with Private Bath

KiraRating, 5 stars1 week ago
Beautiful, well-kept home full of charm and history. Robin was a thoughtful host who made sure we had everything and more to make our stay comfortable. Great location—an easy walk from the train in a quiet, friendly neighbourhood :)

Apartment rentals with breakfast

Private room in Somerville
4.22 out of 5 average rating, 51 reviews

R5 Free Parking Private Room Walk to T & Shops

AuroraRating, 5 stars4 weeks ago
Very nice room and sweet hosts. 10/10 stay highly recommended
Superhost
Private room in Boston
5 out of 5 average rating, 3 reviews

B_Triple Bed Near Downtown Boston (5 miles)

TaylorRating, 5 stars4 weeks ago
Extremely clean, inexpensive option in Boston. Parking can be difficult but I was able to find some on the same street or one street over each of the nights I stayed. Park, Target, and various restaurants nearby made it easy as a place to do remote work from and take breaks and get food.
Superhost
Private room in Everett
4.83 out of 5 average rating, 18 reviews

Nice room, 20 min from Boston, bus stop.

WilhelmRating, 5 stars4 months ago
I enjoyed the time staying in the room. The pictures do a good job of representing the size of the room, and the closet is quite spacious. Adding to that, Simone is a great and very helpful host, and she helped out with everything I needed. I really recommend staying here with Simone as a host.
Apartment in Boston
4.64 out of 5 average rating, 28 reviews

Boston Marathon and Boston Anime!

HectorRating, 5 stars1 week ago
Our stay at this Boston Airbnb was absolutely wonderful. The apartment was spotless, beautifully decorated, and perfectly located—just minutes from the Silver Line bus stop, with easy access to the city center. The property offered a peaceful atmosphere and all the amenities we could have asked for, including a well-stocked kitchen, a comfortable bed, and a cozy living room. Our host Lavette was incredibly responsive and welcoming, providing helpful recommendations for local dining and attractions. Every detail, from the fresh linens to the thoughtful welcome basket, made us feel right at home. If you’re looking for a relaxing and convenient getaway in Boston, I cannot recommend this place highly enough. We’re already looking forward to our next visit!
Private room in Medford
New place to stay

Studio Near Tufts University.

DevinRating, 5 stars1 week ago
Our stay at Mary’s place was absolutely wonderful. She was friendly, welcoming, and incredibly responsive to any messages we sent. One highlight was her recommendation of a local Mexican restaurant—it was outstanding! Her home is beautifully decorated and thoughtfully stocked with everything we needed and more. The walk to the studio takes you through her gorgeous outdoor garden, which added such a peaceful touch to the experience. All in all, it was a fantastic stay, and we would definitely return!
Private room in Malden
4.64 out of 5 average rating, 11 reviews

Lovely one bedroom one bath rental in Malden ma

NguyenRating, 5 stars6 months ago
Christian's place was exactly what we needed for the weekend while we spent the day in Salem. He responded quickly and was very helpful the whole weekend. I would definitely book again the next time I'm in Boston!
Guest favourite
Private room in Cambridge
4.71 out of 5 average rating, 515 reviews

Quiet private room in N. Cambridge

Jeong HyunRating, 5 stars2 weeks ago
John's a wonderful host! He's met a lot of people from all over the world and has a lot of stories to tell, very pleasant to chat with and makes you feel at home. The location is great, with very easy access to public transportation (both bus and train). The neighborhood is quiet and the bed is comfortable. I slept really well. John also let me use his guest parking permit so I could park my car on the street which was really nice of him. Highly recommend!
Superhost
Private room in Watertown
4.85 out of 5 average rating, 213 reviews

Bedroom w shared kitchen, bathroom & living room

NafisaRating, 5 stars1 week ago
Patrick was a great host, very kind and attentive. He left some recommendations for places to visit, and I really enjoyed the city diner, their breakfast menu and milkshakes. The room is small, but has everything you need for a short stay. I was also grateful for being able to wash my clothes during my stay, as it rarely possible in Airbnbs. Other tenants Masoud and Jon were also kind, so I had overall very positive impressions and will gladly come back again.

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.
Guest favourite
Private room in Arlington
4.97 out of 5 average rating, 310 reviews

Arlington Craftsman Blue Room, Int. Well Restored

DavidRating, 5 stars1 week ago
Excellent airbnb, in a really cool neighborhood in Arlington. Thomas is a great host, check-in was easy, and everything went smoothly. Thomas even provides breakfast in the morning, which was an unexpected bonus. Its also only a short walk to many cafes and restaurants in Arlington, as well as bus stops where you can take a bus to the red line stations. I had an enjoyable stay at Thomas's house, and would highly recommend his place to others!
Top Guest favourite
Private room in Cambridge
4.98 out of 5 average rating, 297 reviews

Smack dab between Harvard+Porter 2

KennethRating, 5 stars1 week ago
I’ve stayed in several properties in the Cambridge-Boston area. Of all those experiences, this one was my very favorite. I loved conversing with her, the beauty of my view and its proximity to the gathering places of perhaps the most interesting collection of humanity in the Americas
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.
Guest favourite
Private room in Somerville
4.91 out of 5 average rating, 906 reviews

Peter • Best of Boston

Conrad & JodiRating, 5 stars2 weeks ago
Great place to land while in the Boston area. It's a bit of a challenge to get to, and parking is tight, but that's everywhere in Somerville. But worth the effort. Loved the space, comfy, everything you need.
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 Cambridge
4.84 out of 5 average rating, 186 reviews

A Room at the Top-sep. entrance, private bath

DeirdreRating, 5 stars1 month ago
Joan’s room was exactly what I was looking for! Quiet, tidy, and walkable. Providing breakfast was a lovely bonus.
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!

Destinations to explore