Leonardtown Vacations

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Find the Best Leonardtown Vacation Packages

Leonardtown Hotel Deals

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

2.5 out of 5
41655 Park Avenue Leonardtown MD
Fully refundable
The price is SARĀ 541 per night from Aug 6 to Aug 7
SARĀ 541
SARĀ 601 total
6 Aug - 7 Aug
includes taxes & fees
9.4/10 Exceptional! (181 reviews)
"This hotel is very cute, clean and centrally located to the downtown Leonardtown area. Parking was very accessible and easy and I loved that breakfast was included. My only issue was the woman working at the front desk when we checked in. She was grumpy and not very friendly. We arrived at noon so ..."

Reviewed on 23 June 2026

The Inn at Leonardtown, an Ascend Collection Hotel
River Edge Inn

River Edge Inn

2.5 out of 5
30 Colonial Ave Colonial Beach VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 355 per night from Jul 20 to Jul 21
SARĀ 355
SARĀ 433 total
20 Jul - 21 Jul
includes taxes & fees
River Edge Inn
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
The price is SARĀ 343 per night from Aug 3 to Aug 4
SARĀ 343
SARĀ 381 total
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (155 reviews)
"This hotel doesn't honor requests for stay in non-pet rooms when you have allergies. The rooms have major odor issues."

Reviewed on 15 July 2026

avid hotel California - Lexington Park by IHG
See all 575 properties in Leonardtown
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.

Stay near popular Leonardtown attractions

Leonardtown Town Hall

This historic building serves as the heart of Leonardtown's civic operations and community gatherings. Combine your visit with a stroll through the charming downtown area to experience local culture.
See properties

Frequently asked questions

How much does a Leonardtown vacation package cost?
You'll find cheap prices on Expedia for your Leonardtown break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Leonardtown costs.
What are the cheapest months to go to Leonardtown?
If you're looking to snag a cheap Leonardtown vacation package, consider planning a trip in January, March and September. You'll typically find lower prices on airfares and hotels during these months ā€” perfect for budget-conscious travelers.
How to find the best Leonardtown package deals?
Begin your search for a Leonardtown package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Leonardtown package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Leonardtown adventure underway.
Is it cheaper to book a Leonardtown vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Leonardtown vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Leonardtown?
If you're considering a spontaneous Leonardtown vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Leonardtown?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Leonardtown.
  2. Set your budget: Consider expenses such as flights, food and transportation when working out how much to save for your trip to Leonardtown. Then, choose a hotel that suits your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide your trip length: Think about how long you want to spend discovering Leonardtown. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Leonardtown vacation package for you.