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Our top choices for Middletown bed & breakfast

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
$257 nightly
The price is $286
Dec 16 - Dec 17
Total with taxes and fees
James Pharmacy Bed & Breakfast

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
$238 nightly
The price is $264
Dec 30 - Dec 31
Total with taxes and fees
The Captain Stannard

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
$222 nightly
The price is $246
Dec 16 - Dec 17
Total with taxes and fees
Westbrook Inn B&B

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (89)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
United States
Cynthia
$313 nightly
The price is $347
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Homestead

The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (81)
"The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment. "
United States
Juliette
$236 nightly
The price is $263
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Bevin House Bed & Breakfast

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

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Hamden
$852 nightly
The price is $965
Dec 16 - Dec 17
Total with taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
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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Top Middletown Hotel Reviews

Find out more about Middletown

Middletown B&B information

Number of reviews
619
Accommodation
11 B&B
Lowest Price
$246
Highest Price
$965

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 $246 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.

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