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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

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

The Captain Stannard
Standard Room, 1 Bedroom, Private Bathroom | Free WiFi, bed sheets

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (217)
"Clean, classic, charming seaside New England inn. Unique in that it isn’t really staffed in the traditional sense but provided much more than we expected - 24 hour guest pantry, beautiful common spaces to relax, fresh cookies upon arrival, and basic breakfast. This will be our new go-to when we’re in the area. "
The price is AED 523
AED 580 total
includes taxes & fees
3 Apr - 4 Apr
The Captain Stannard
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (236)
"Amazing and too short. Loveliest little B&B with one of the best breakfasts I've ever had. Incredibly clean with updated bathroom(s). So quiet, even though almost full. Will be going back, regularly!"
The price is AED 943
AED 1,047 total
includes taxes & fees
14 Apr - 15 Apr
The Scranton Seahorse Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (147)
"It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable."
The price is AED 680
AED 755 total
includes taxes & fees
1 Apr - 2 Apr
Westbrook Inn B&B
The Bevin House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, sun loungers

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (73)
"I really wanted to see the goats as silly as that sounds and had a great time doing it."
The price is AED 935
AED 1,038 total
includes taxes & fees
1 May - 2 May
The Bevin House Bed & Breakfast
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters

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
14 Apr - 15 Apr
The Homestead
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

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
1 Apr - 2 Apr
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
James Pharmacy Bed & Breakfast
Garden

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. "
The price is AED 1,110
AED 1,673 total
includes taxes & fees
1 Apr - 2 Apr
James Pharmacy Bed & Breakfast
Jay's Ranch
Exterior

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. "
The price is AED 319
AED 459 total
includes taxes & fees
1 Apr - 2 Apr
Jay's Ranch
Thimble Islands Bed & Breakfast
Property grounds

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
Aerial view

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
Green Acres B&B
Seasonal outdoor pool

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, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is AED 496
AED 570 total
includes taxes & fees
29 Apr - 30 Apr
Postcard Cabins Machimoodus
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun loungers, beach towels

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Tuvimos un finde increíble en la casa, súper cómoda y bonita "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches
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 Connecticut Valley Railroad State Park Trail 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?
Here is a B&B that guests like in the surrounding area: The Bevin House Bed & Breakfast: 5 rooms. 7.5 mi (12.1 km) from the heart of downtown. 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 Wadsworth Falls State Park 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.