A rural landscape with a barn, trees, and a fence under a sunset sky.

Book Leonardtown Bed & Breakfast

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Our top choices for Leonardtown bed & breakfast

1. Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay
2.0 star property
St. Leonard
10.0 out of 10, Exceptional, (1 review)
"This is a must see for yourself!! The owners have thought of every detail from the over the top welcome amenities to extras like offering beach chairs and towels to go explore the local beach! Breakfast was absolutely delicious! She even prepared a to go breakfast when she found out we had to leave out early one morning! We enjoyed home grown fruits and veggies from her garden daily! If you want to step back in time, but still have the comforts of modern day you have to got to visit this place!...
United States
Jessica
$114 nightly
The price is $127
Sep 21 - Sep 22
Total with taxes and fees
Historic 1825 Chesapeake Farm Stay

2. Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland
5.0 star property
Ridge
9.8 out of 10, Exceptional, (34 reviews)
"A beautiful stay with amazing hosts!"
United States
Vineet
$302 nightly
The price is $335
Sep 30 - Oct 1
Total with taxes and fees
Swanendele Inn at St. Mary's Maryland
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 Leonardtown Hotel Reviews

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Leonardtown B&B information

Number of reviews
1
Accommodation
5 B&B
Lowest Price
$127
Highest Price
$335

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Leonardtown?
Prices for B&Bs in Leonardtown often vary, but you can find a great deal from $127 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Leonardtown 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 Leonardtown?
The best time to book a B&B in Leonardtown is during the spring months, particularly from April to June, when the weather is pleasantly mild and the scenery is in full bloom. This vibrant period attracts travelers who enjoy outdoor activities, cultural festivals, and the charm of historic towns. The average temperatures during these months range from the mid-50s to the low 80s Fahrenheit, creating an inviting environment for exploring the picturesque waterfront and quaint shops.

April and May are particularly delightful, as visitors can partake in local events such as the annual Leonardtown Arts & Entertainment District events and outdoor farmers' markets. These gatherings offer a great way to immerse yourself in the local culture while enjoying the fresh spring air.

For those looking for a more budget-conscious option, consider visiting in December. While the weather may be cooler, with temperatures dipping into the low 40s Fahrenheit, the holiday season brings a festive spirit to Leonardtown, complete with charming decorations and seasonal events that create a cozy atmosphere.
What is the difference between a Leonardtown Bed & Breakfast and a hotel?
Every Leonardtown 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 Leonardtown B&Bs.

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