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Book Middletown Bed & Breakfast

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Compare 11 B&B in Middletown with updated reviews, rates, and availability.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (219)
"Wonderful welcome and impeccable property. We will plan to go again!"
The price is $219
includes taxes & fees
$197 per night
May 5 - May 6
The Captain Stannard

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (150)
"It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable."
The price is $229
includes taxes & fees
$206 per night
May 7 - May 8
Westbrook Inn B&B

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 $286
includes taxes & fees
$257 per night
Jun 2 - Jun 3
The Bevin House Bed & Breakfast

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Wonderful rooms, exceptional staff, and convenient location"
The price is $382
includes taxes & fees
$344 per night
May 4 - May 5
The Homestead

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

The price is $1,067
includes taxes & fees
$943 per night
May 4 - May 5
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is $455
includes taxes & fees
$422 per night
May 4 - May 5
James Pharmacy Bed & Breakfast

Jay's Ranch

4.0 star property
7.8 out of 10, Good, (38)
"Quiet and safe "
The price is $125
includes taxes & fees
$109 per night
May 4 - May 5
Jay's Ranch

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
Thimble Islands Bed & Breakfast

The Connecticut River Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (24)
"Charming Inn, "
The Connecticut River Valley Inn

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

2.0 star property
10.0 out of 10, Exceptional, (9)
"I love this place "
The price is $159
includes taxes & fees
$139 per night
May 5 - May 6
Postcard Cabins Machimoodus

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (10)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is $384
includes taxes & fees
$338 per night
May 4 - May 5
Blue Back Bungalow
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

What is the nightly rate for a B&B in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $125 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Middletown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Middletown?
The best time to book a B&B in Middletown is during the vibrant summer months, particularly from June to August. This period is characterized by warm temperatures, typically ranging from the mid-70s to the low 90s Fahrenheit, making it ideal for those who enjoy outdoor activities and the lively atmosphere of summer festivals. Visitors can indulge in a variety of experiences, from exploring the scenic vineyards to enjoying local events that highlight the region’s rich culture.

July stands out as the most popular month, drawing travelers eager to soak up the sun and participate in local celebrations. The atmosphere is electric, with a plethora of activities available, whether you’re interested in hiking picturesque trails or savoring wine tastings at nearby wineries.

If you’re looking for a more budget-friendly option, consider visiting in October. This month offers a unique charm with the fall foliage painting the landscape in beautiful hues, creating a picturesque backdrop for leisurely drives and peaceful hikes. The crowds are thinner, allowing for a more intimate experience with the local culture and scenery.
What is the difference between a Middletown B&B and a hotel?
Every Middletown B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Middletown B&Bs.