Leonardtown Holidays

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Leonardtown Holiday

Our pick of the best 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 NZ$298 per night from 26 July to 27 July
NZ$298
26 July - 27 July
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
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 NZ$188 per night from 23 July to 24 July
NZ$188
23 July - 24 July
includes taxes & fees
9.4/10 Exceptional! (140 reviews)
"A good over night accommodation. Staff was very helpful and friendly. Plenty of eating places near by. A good place to stay if your touring Southern Maryland."

Reviewed on 1 July 2026

avid hotel California - Lexington Park by IHG
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 NZ$199 per night from 8 July to 9 July
NZ$199
8 July - 9 July
includes taxes & fees
River Edge Inn
See all 574 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

Sandyland Beach

This secluded shoreline offers a tranquil escape from Maryland's busier beaches along the Chesapeake Bay. Bring your own supplies and enjoy the unspoiled natural setting perfect for peaceful beachcombing.
See properties

Frequently asked questions

How much does a Leonardtown holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday to Leonardtown costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Leonardtown?
January, March and September are great times to look for cheap Leonardtown holiday packages. Opting to travel in quieter months means you'll typically find better prices on hotels and flights.
How many days is enough for Leonardtown?
Generally, a handful of days is enough to explore the main sights during your Leonardtown holiday. But if you want to have time to unwind or go on day tours, think about extending your trip.
How to find the best Leonardtown package deals?
Finding a cheap Leonardtown package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can customise your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Leonardtown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Leonardtown holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging flights and stays separately. Better still, you can personalise your Leonardtown getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Leonardtown?
Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Leonardtown trip.
How to plan a trip to Leonardtown?

  1. Pick your travel dates: What you'd like to do in Leonardtown and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in expenses such as flights, food and transportation when working out how much to put aside for your trip to Leonardtown. Then, choose a hotel that matches your budget, whether that's an affordable stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you're up to speed on Leonardtown, you can figure out the ideal length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Leonardtown holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.