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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 12 B&B in Middletown with updated reviews, rates, and availability.

The Scranton Seahorse Inn
Front of property

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (235)
"This was a one night stay. The property is an older house in the city center. We were here to help a friend celebrate a birthday. The B&B was very close to the party making it easy to come and go. The room was small but comfortable. The bed was very comfortable. Breakfast was fantastic. "
The price is AED 862
AED 957 total
includes taxes & fees
24 Feb - 25 Feb
The Scranton Seahorse Inn
The Homestead
Exterior

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Charming in every aspect. Highly recommend, Hosts are wonderful people."
The price is AED 930
AED 1,032 total
includes taxes & fees
13 Mar - 14 Mar
The Homestead
Westbrook Inn B&B
Dock

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (144)
"The host was very friendly and helpful. The property was well maintained. It is quite and we enjoyed our stay. "
The price is AED 789
AED 876 total
includes taxes & fees
24 Feb - 25 Feb
Westbrook Inn B&B
Jay's Ranch
Terrace/patio

Jay's Ranch

4.0 star property
7.8 out of 10, Good, (37)
"The hostess Rene was very friendly and accommodating. The room was spacious and clean, with comfortable bed and linens. I was pleasantly surprised that I had my own toilet. It was nice to have access to the kitchen and living room. "
Jay's Ranch
The Captain Stannard B&B Country Inn
Exterior

The Captain Stannard B&B Country Inn

3.0 star property
9.6 out of 10, Exceptional, (214)
"We had a wonderful time and the owner was great. We had a fun time talking about history of both inn’s. Look forward to returning and doing more next time"
The price is AED 659
AED 732 total
includes taxes & fees
27 Feb - 28 Feb
The Captain Stannard B&B Country Inn
The Bevin House Bed & Breakfast
Exterior detail

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (70)
"Our room was beautiful, spacious and clean, with a wonderful bathroom. The innkeeper was friendly and very helpful and provided a delicious breakfast."
The price is AED 895
AED 994 total
includes taxes & fees
24 Feb - 25 Feb
The Bevin House Bed & Breakfast
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Interior

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

The price is AED 2,571
AED 3,889 total
includes taxes & fees
23 Feb - 24 Feb
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
James Pharmacy Bed & Breakfast
Room

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
James Pharmacy Bed & Breakfast
Thimble Islands Bed & Breakfast
Front of property

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"Property was first class inside and out. The view was breath taking The owners made us feel at home and did not want to leave ! Already thinking about next trip back."
Thimble Islands Bed & Breakfast
The Connecticut River Valley Inn
Lobby sitting area

The Connecticut River Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (24)
"The Inn and the innkeepers were lovely. The decor is quirky and elegant at the same time. Every convince is thought of. The fireplace in every room is a fabulous touch. We can’t wait to visit again soon"
The Connecticut River Valley Inn
Captain Josiah Cowles Place
Exterior

Captain Josiah Cowles Place

3.0 star property
10.0 out of 10, Exceptional, (19)
"This is a beautiful old home (c 1730), that is now used as an Inn-B&B establishment. It is very beautiful, clean and the owners provided a great breakfast and great hospitality ....which included the owners hand made Maple syrup made from the owners' Sugar Maples on the property. It was quite an experience, a real treat to be vacationing for a night in a home/Inn that was built before the Revolutionary War was even thought of and on the National Registry of Historic Homes/Buildings......It...
Captain Josiah Cowles Place
Green Acres B&B
Exterior

Green Acres B&B

3.0 star property
9.8 out of 10, Exceptional, (150)
"Gracious hosts, many amenities and the best breakfast!"
Green Acres B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Middletown

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
Postcard Cabins Machimoodus
Waterfront House with picture-perfect views from all 3 levels.
Third level patio, off of bedroom with queen bed and twin bed with trundle.

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
The house from the driving shows the jelly shed and the corn crib.

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.8 out of 10, Exceptional, (127)
"We loved our stay!"
The price is AED 1,010
AED 2,125 total
includes taxes & fees
26 Feb - 27 Feb
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Middletown?
If you’re looking for something a little different than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. If your ideal vacation to Middletown includes spending lots of time outside, General Mansfield House and Smith Park are good spots to enjoy the scenery.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to interact with the owner, and of course a scrumptious breakfast, B&Bs offer a one-of-a-kind environment.
What are the best bed and breakfasts in Middletown?
Below is a B&B in the surrounding area: The Bevin House Bed & Breakfast: 5 rooms. Located 7.5 mi (12.1 km) from the core of Middletown. Enjoy the free full breakfast and designer toiletries.
When should I book my B&B in Middletown?
When you’re dreaming of a trip to Middletown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Middletown is 53 inches.
What is there to do in Middletown?
When you want to spend some time in the great outdoors, Connecticut River and General Mansfield House are some notable spots. You might put Wadsworth Mansion and Kidcity Children’s Museum on your list if you want to see more of the area.
How can I get to and around Middletown?
Planning your excursions in and around Middletown is easier with these transportation options. Fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is located 23.8 mi (38.2 km) away from the city center. You can also search for flights into Bradley Intl. Airport (BDL), which is 25.5 mi (41 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.