Bed and breakfast holiday rentals in Middlesex County

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Top-rated bed and breakfasts in Middlesex County

Guests agree: These bed and breakfast rentals are highly rated for location, cleanliness and more.

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Superhost
Hotel room in Madison
5 out of 5 average rating, 3 reviews

The Town View

What a rare treat to delight in a large and roomy space all to yourself in a quaint historical home. Be surrounded by five sunny windows that offer a panoramic view from so many different vantage points. The cozy nook with sofa bed, chairs, and desk with chair are perfect for sharing wine and cheese or to read a book. Slumber in the comfy queen sized bed and enjoy the bright bathroom with Jacuzzi tub and gentle rain shower that complete this guest room. This guest room is not pet friendly.

Superhost
Private room in East Hampton
4.89 out of 5 average rating, 9 reviews

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

Bed & Breakfast located in East Hampton. This historic mansion was build in 1872 and has 15 Rooms including a Library with over 1200 books. The outside has a wrap around deck, in ground heated pool and a gated entrance. Located near CT wine trail, Rule of 3's brewery, Airline hiking trail & much more... Each stay includes a gourmet breakfast. The Abner & William rooms share a bathroom on the 3rd floor. The Chauncey & Stanley share a bathroom on the 2nd floor. Philo has a private bathroom.

Guest favourite
Guest suite in Mystic
4.89 out of 5 average rating, 93 reviews

Pet Friendly King Suite 3 Min Walk Downtown, Charm

There are 2 seperate suites for rent. These are not connected but both open up to a large, private terrace surrounded by gardens. Relax and enjoy the charms of downtown Mystic. Located on the historic property of Captain William Morgan, an 18th century sea captain, this private Carriage House is situated just a 1/4 block from downtown, in the heart of Mystic, but also quiet & secluded. The larger suite sleeps 3 with a king bed and smaller full size futon. The smaller suite has a king bed.

Guest favourite
A cozy bedroom features a twin antique Victorian brass bed, topped with fine linens. Two lamps provide soft lighting, and a mirror hangs on the wall, reflecting the warm tones of the room. A wooden chair and a partial view of decorative artwork enhance the inviting setting.
Private room in New Haven
4.83 out of 5 average rating, 232 reviews

“Cambridge "room in Carriage house

Be our Guest , in the serviced apartment Close to SOM & Yale sciences Walk to town and all of Yale Share this Carriage house with two other rooms. Lovely cozy locked bed room twin antique Victorian brass bed Fine linens , robe provided Two windows Oriental carpet, antique armoire Dresser, high ceilings, Continental breakfast,stocked kitchen FREE WIFI , complementary linen service ,laundry room shared bathroom dinning room ,sitting room keyless entry Off st. parking available for fee

Guest favourite
Private room in Guilford
4.75 out of 5 average rating, 273 reviews

Private Upstairs Chef’s Suite at Griswold Cottage

This is a Private suite with private bath. My place is close to the Village Green, it’s shops, restaurants, Chocolatier and bookstore. It’s a half mile to the Guilford beach, 4 miles to the Hammonasett beach in Madison. The house has great light, a cozy relaxing porch, a walking location to the village. You want to take a Picnic lunch with you? talk to me... My place is good for couples, solo adventurers, business travelers, bicyclists or hiking enthusiasts, anyone who just loves history!

Guest favourite
An aerial view of a spacious carriage house is presented, surrounded by lush greenery. The building features a long driveway with multiple garage doors and a wide porch area with seating. Soft clouds drift across a blue sky above, enhancing the serene setting.
Cottage in Lyme
5 out of 5 average rating, 21 reviews

Bucolic Farm On A Country Road

Lovely private 1 bedroom apartment with shared entry. Located in bucolic Lyme Ct. which has nearby beaches, tourist attractions, nature parks, small town living, hiking etc. Sparkling clean! Fully equipped kitchen, dining and living spaces incl laundry. Enjoy the outdoor sitting area with sounds of nature and wildlife. Comfortable furnishings, include a sleeper sofa for an extra guest or 2! Private and peaceful yet close to shopping, dining, area attractions and nature pursuits.

Guest favourite
Private room in Windsor
5 out of 5 average rating, 11 reviews

Breakfast is the most important meal of the day!

Foodies will love this experience! We are very serious about breakfast, your meal will be prepared specifically for you each morning of your stay. We take pride in unique and delicious offerings using locally sourced seasonal options. Your room, The Avery is an oasis in time and space with gorgeous 1920's floral wallpaper, custom drapes, & luxury bedding. State of the art environment controls and plenty of charging stations for your devices. For more details explore Reaulthouse

Guest favourite
A cozy bedroom features a spacious bed adorned with a floral comforter and decorative pillows. Two bedside lamps provide soft lighting, while a vintage mirror and framed artwork hang on the vibrant blue walls. A comfortable armchair with a patterned fabric is positioned near the window.
Private room in Sag Harbor
4.92 out of 5 average rating, 156 reviews

Peaceful Sag Harbor Geodesic Dome home

Convenient to all of the Hamptons, Sag Harbor has an amazing harbor, fabulous restaurants, cool mom-and-pop shops, and a quaint New England vibe. The most picturesque spot in the Hamptons, Sag Harbor is truly a gem. My house is a Buckminster Fuller-designed geodesic dome home. You'll be in a quiet cul-de-sac community 1 mile from Main Street with access to the back deck. Please check out all the photos to ensure my place is perfect for you.

Top Guest favourite
Private room in Colchester
4.95 out of 5 average rating, 111 reviews

Johnston Room at The O'Connell House Inn

*Our Inn features 4 unique guest rooms to choose from! Rooms accommodate 2-4 guests. Preview them all on our website or host’s Airbnb profile. Set in the heart of Colchester’s quaint downtown Village District, and overlooking the Town Green, The O’Connell House is an 1840 Greek Revival that has been thoughtfully renovated to showcase historic character and modern amenities. Conveniently central to downtown, local and regional activities.

Guest favourite
A serene bedroom features a spacious bed with light linens, complemented by white bedside tables and lamps. A desk with a comfortable chair is positioned near a large window, offering wooded views. Fresh towels are neatly arranged on the bed, enhancing the room's inviting atmosphere.
Private room in Manchester
4.97 out of 5 average rating, 30 reviews

2 Bedroom Suite, Full Bath, Country Setting

B and B with 2 Bedrooms and Bath comprise a private suite on second floor in an owner occupied home. Natural setting on 3 acres of tall oak & pine. Easy drive to City or Colleges, it’s a great refuge after a busy day’s activities or sightseeing. Kitchen is open 7-10 am for coffee and continental breakfast with an outdoor patio available. Cooking privileges are not included. Tell us who will accompany you & why you chose our place.

Guest favourite
The main living area showcases a cozy sofa, complemented by a vibrant throw pillow. A round coffee table sits atop a patterned area rug. Natural light filters through the windows, illuminating the space and enhancing the modern decor.
Apartment in Mystic
4.86 out of 5 average rating, 474 reviews

Super Cute & Cozy Apartment in Downtown Mystic!

Live large in a small space! This lovely little one bedroom apartment in downtown Mystic packs a surprisingly big punch for its size and is walkable to almost everywhere! The Seaport, the drawbridge, the Amtrak Station are all less than a ten minute walk away. Well-behaved pets are welcome for a $60 fee. Onsite laundry is available in the garage by request.

Guest favourite
Private room in Preston
5 out of 5 average rating, 6 reviews

Morningview Suite | King Bed Lake & Vineyard Views

The Morning View Suite offers a peaceful stay at The Cottage Inn with beautiful lake and vineyard views. Featuring a comfortable king bed and private ensuite bathroom, this inviting suite is just minutes from Foxwoods, Mohegan Sun, Mystic, Groton, Stonington, and Rhode Island. The perfect place to relax after a day of casinos, dining, or coastal exploring.

Popular amenities for Middlesex County bed and breakfasts

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