Book Middletown Bed & Breakfast

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Our top choices for Middletown bed & breakfast

Inn At The Canal Bed & Breakfast

Inn At The Canal Bed & Breakfast
3.5 star property
Chesapeake City
8.6 out of 10, Excellent, (505)
"The property owner, Ed, was fabulous. I cannot say enough wonderful things about his hospitality and the Inn is in a perfect location."
United States
Emily
$145 nightly
The price is $154
Jan 4 - Jan 5, 2026
Total with taxes and fees
Inn At The Canal Bed & Breakfast

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (531)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
$140 nightly
The price is $157
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vandiver Inn

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
Smyrna
10.0 out of 10, Exceptional, (1)
"Overall great place. Nice neighborhood. Very spacious and clean living area. Loved having the pool table and all the games. Lisa is a great host and the breakfast is delicious. "
United States
David W.
$455 nightly
The price is $467
Dec 24 - Dec 25
Total with taxes and fees
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Miller-Dunham House Bed & Breakfast

Miller-Dunham House Bed & Breakfast
3.0 star property
Odessa
10.0 out of 10, Exceptional, (85)
"The Provence room was beautiful, Heather and TJ were very warm and friendly. Everything was exceptionally clean. No complaints. "
United States
Matthew
$230 nightly
The price is $240
Dec 23 - Dec 24
Total with taxes and fees
Miller-Dunham House Bed & Breakfast

Elk Forge B&B Inn & Day Spa

Elk Forge B&B Inn & Day Spa
2.5 star property
Elkton
8.8 out of 10, Excellent, (184)
"A beautiful little B&B, provides a snapshot of yesteryear and I appreciate that. Room was clean, and the surrounding area is absolutely beautiful, with a park nearby for walks. "
United States
Sarah
$129 nightly
The price is $137
Dec 23 - Dec 24
Total with taxes and fees
Elk Forge B&B Inn & Day Spa
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
823
Accommodation
7 B&B
Lowest Price
$137
Highest Price
$467

Frequently asked questions

What are the most popular Middletown Bed and Breakfasts?
Rustic Elegance Meets Outdoor Charm - 2 bedroom Middletown is an inviting choice for travelers seeking a blend of comfort and nature. This property highlights thoughtful amenities like onsite parking through a third-party service, making it easy to come and go as you explore the beautiful surroundings of Middletown. With its cozy ambiance, it's superb for couples looking to unwind and reconnect in a serene setting.
What is the nightly rate for a Bed & Breakfast in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $137 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 and Breakfast in Middletown?
The most popular time to book a B&B in Middletown is during the vibrant summer months of June through August. This is when visitors flock to enjoy the area's beautiful landscapes and partake in outdoor activities such as hiking, biking, and exploring the picturesque vineyards that define the region. With warm temperatures typically ranging from the mid-70s to the low 90s Fahrenheit, it's an ideal setting for those who appreciate sun-soaked adventures and lively local events.

In particular, July stands out as the high point of the season, drawing crowds eager to experience community festivals and outdoor concerts that fill the air with joy and excitement. The lively atmosphere during this peak period creates a fantastic opportunity for travelers to connect with fellow adventurers and engage in the local culture.

For those looking for a more budget-friendly option, late fall, particularly November, offers a delightful alternative. While the tourist numbers dip, visitors can still enjoy the serene beauty of Middletown, with the added benefit of fewer crowds. This month provides a great backdrop for peaceful vineyard tours and scenic walks, allowing for a more intimate experience of the region's charm.
What is the difference between a Middletown Bed & Breakfast 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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