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Bed and breakfast holiday rentals in Middlesex County

Find and book unique bed & breakfast rentals on Airbnb

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Popular amenities for bed & breakfast rentals in Middlesex County

Family-friendly bed & breakfast rentals

Top guest favourite
Private room in Hamden
5 out of 5 average rating, 30 reviews

Beautiful au pair suite - 800 sq ft

TeresaRating, 5 stars3 weeks ago
I have stayed with Laura before and it is always a good experience! Lovely accomodations, thoughtful touches and a friendly host!
Hotel room in Cornwall
5 out of 5 average rating, 5 reviews

Cornwall Lodge - King Room (pet friendly)

RobertRating, 5 stars42 months ago
Stacey was sweet and gracious. The Cornwall Inn is a cute little inn that is a mix of inn and roadside motel. We stayed in a room in the motel part and felt comfortable. The entire place was well maintained and cleaned. Nice job Stacey and family! We will be back!
Private room in Mystic
5 out of 5 average rating, 32 reviews

Mermaid Inn - Mermaid Room

BrittanyRating, 5 stars58 months ago
The Mermaid Inn was magical in every aspect. Josephine is the most gracious host, and her culinary skills are unmatched!
Hotel room in Cornwall
4.94 out of 5 average rating, 17 reviews

Cornwall Lodge - Queen Room (pet friendly)

BelindaRating, 5 stars13 months ago
Lovely place, very clean. Will be back.
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 stars8 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!
Private room in Cornwall

Cornwall Inn - Two beds (sorry, no pets)

GenyRating, 5 stars11 months ago
Una experiencia muy agradable , volveremos!
Superhost
Private room in Shelter Island
4.85 out of 5 average rating, 20 reviews

Candlelite Inn queen room private detached bath

IanRating, 5 stars35 months ago
John's bed and breakfast / the Candlelight Inn is a wonderful experience. The room was clean, beautifully kept and just as advertised. I would highly recommend this stay and shelter island in general, as there are many beautiful beaches, stores and restaurants all 5-10 minutes away. The final night of our stay ended with our eating dinner on the porch with fireflies and other guests. We even snagged some furniture from the thrift store across the street!
Hotel room in Cornwall
5 out of 5 average rating, 6 reviews

Cornwall Inn - Suite w/2 bedrooms (sorry, no pets)

DianaRating, 5 stars21 months ago
Very beautiful place and peaceful surroundings. Breakfast is really good and hosts are very nice and friendly. The rooms were very clean and spacious. We enjoyed our stay

Bed and breakfast rentals with breakfast

Private room in Shelter Island Heights
5 out of 5 average rating, 4 reviews

SEVEN on Shelter - Queen Guest Room

NicoleRating, 5 stars13 months ago
What a perfect spot in Shelter Island! Beth and team were amazing - we were visiting one night for a wedding on the island and the ceremony was at 2 PM the day we were arriving. I messaged Beth and she was extremely helpful with providing early check in to ensure we could get ready prior to the event! The actual B&B is beautiful - fantastic design, super clean, cool art and the backyard area with the pool is so dreamy. There is even a little workout area near the pool with a Peloton and a Lululemon mirror. Its a short drive from the North ferry, lots of restaurants and cafes and only a short walk to the beautiful Crescent beach. It is such a serene setting and I truly feel like I am on vacation.The room was beautiful and the bed was comfy, I am OBSESSED with the hand soap and have to find it for myself because it smells SO GOOD! I would 100000% recommend staying here and I will definitely be back!
Top guest favourite
Private room in Colchester
4.95 out of 5 average rating, 96 reviews

The Johnston Room at The O'Connell House B&B

JaneRating, 5 stars4 weeks ago
Brian and Jean were wonderful hosts. Their B&B is warm and welcoming. Our room was clean and cozy. After a delicious breakfast make by Brian, we left well rested and well fed!
Private room in East Hampton
4.97 out of 5 average rating, 33 reviews

The Bevin House B&B, 2 people, Chauncey Rm

WesleyRating, 5 stars11 months ago
Brilliant! Our stay was everything I needed and more. The house and amenities were perfect for the trip and no matter the time or the request, they took care of everything. We had some amazing conversations and the lemon cupcakes are to die for!! thanks for everything
Guest favourite
Private room in Roxbury
4.98 out of 5 average rating, 40 reviews

Mine Hill Getaway West Room

SarahRating, 5 stars8 months ago
Renee was a very nice host. The room was clean and the bed comfortable!
Top guest favourite
Private room in Pomfret
5 out of 5 average rating, 47 reviews

Barn Swallow Suite @TONMAR

EileenRating, 5 stars1 month ago
I love this place so much that I almost wish I could keep it a secret, but then all you wonderful people wouldn't experience being hosted by Martha and Tony. Idyllic doesn't even begin to describe their gorgeous property and you'll have a separate space from the main house to stay in - a renovated barn with a generously sized suite for guests. The space is filled with antiques, and you can tell that each one has its own story. The bed is super comfy, the room has a modern split system to keep the space at the right temperature, and the bathroom is pristine and has everything you need. What makes each stay really special is the farmer's breakfast that Martha brings to her guests in the morning, filled with fresh and warm goodies for every palate. Martha herself has become a dear friend to me over the years and I look forward to staying with her again in October.
Private room in Westbrook
5 out of 5 average rating, 9 reviews

Dog Friendly Salt Island Room at The Westbrook Inn

SamanthaRating, 5 stars21 months ago
Amazing inn, so clean - great location, their team paid attention to details and I slept like a rock. Thank you Meri!
Top guest favourite
Private room in Stonington
4.93 out of 5 average rating, 14 reviews

House of 1833 Bed and Breakfast...The Ivy Room

AmeliaRating, 5 stars5 months ago
One night will never be enough. When you first walk in you are immediately immersed into another world. A world of a life well lived.. a world full of stories. We didn’t want to leave and have already decided to return! Thank you Evan!
Superhost
Hotel room in Madison
5 out of 5 average rating, 5 reviews

The Seahorse

StephanieRating, 5 stars6 months ago
This was a quick overnight trip but wow, was I impressed. To have a place that welcomes dogs, and yet is so pristine and welcoming. I’m disappointed to have missed breakfast with the group. I would absolutely stay here again if I find myself on the S side of CT. Thank you for being to prompt and responsive and making check in so easy Michael!

Bed and breakfast rentals with a patio

Top guest favourite
Private room in Stonington
5 out of 5 average rating, 18 reviews

Private Room E at Dragonfly Inn

YasminaRating, 5 stars8 months ago
My daughter and I fell in love with the Dragonfly Inn. We are huge Gilmore Girls fans, so that was our initial draw, but our expectations were exceeded before we even arrived. The hosts are so communicative and we were made to feel right at home. The property is far enough from the hustle and bustle that you can truly relax but close enough that its a quick trip to local attractions. The Inn and its surrounding property are beautiful and we were even able to peek in to see the horses! We’re already discussing with our family to visit again soon!
Top guest favourite
Private room in Putnam
4.98 out of 5 average rating, 88 reviews

The Albert C Luke House

Learner-AdamsRating, 5 stars2 weeks ago
Charles was a friendly and responsive host. The location was beautiful and close to shopping and restaurants. We loved our stay. The house was gorgeous.
Superhost
Private room in Preston
5 out of 5 average rating, 3 reviews

Lake - Vineyard - Casinos Cottage Inn 2nd Flr/#2

LoriRating, 5 stars12 months ago
We stayed here recently because we had a trip at the casino planned. We felt right at home. Rooms were cozy and comfortable very clean. John was accommodating knowledgeable and very responsive. The property is beautiful and peaceful. Next time we plan on going up to the casino and spending the night, we would book again. Yes, girl.
Guest favourite
Private room in Southold
5 out of 5 average rating, 14 reviews

Vine + Sand Southold, NY's Newest B&B-Room 3

MichelleRating, 5 stars2 months ago
What an amazing stay and such fabulous hosts! The home has so much charm and character with exquisite detail and high end amenities. Mark and Johnny went above and beyond to make our stay incredible! When I left, I felt like I was leaving my family! I can't wait to return!
Private room in New Haven
5 out of 5 average rating, 11 reviews

THE EMERALD INN AUTHENTIC BED & BREAKFAST

CharlesRating, 5 stars3 weeks ago
Nora was an exceptional host, very accommodating, helpful and friendly. She provides a great breakfast . Our private room had a private bath outside the room, which was no problem. I highly recommend Nora's BnB.
Private room in West Haven

A home made comfortable for Yale university staff

DavidRating, 5 stars37 months ago
Fantastic value and location!
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!!
Superhost
Private room in Preston
5 out of 5 average rating, 3 reviews

Lake -Vineyard - Casinos Cottage Inn 2nd Flr/ #3

NickRating, 5 stars11 months ago
Absolutely loved my stay at the cottage. The property is so peaceful and beautiful, it was the perfect place to escape. I stayed in room 3 and found the bed extremely comfortable, with soft, great quality sheets, blankets, pillows and towels. The AC works great and you can control the temp for your own room. The rooms do share walls with other guest rooms, but I was lucky and my neighbors were also quiet and considerate so it was not a problem at all. Coffee, bagels and cereal are always available in the nicely appointed shared kitchen, which also has full fridge, microwave and oven for you to use. Loved looking out over the vineyard with my morning coffee and taking a dip in the lake! 10/10 recommend, can't wait to come back again!

Destinations to explore