Leonardtown Holidays from £507

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Your Leonardtown Holiday

The rich history and coastal scenery are just the start of the things Leonardtown has to offer. Discover the best parts of this captivating city your way with a customised Leonardtown holiday package. A trip to Leonardtown is a terrific opportunity to see the sights. Be sure to look around big-name attractions such as St. Marys River State Park, Port of Leonardtown Winery and New Towne Neck State Park. Whoever you're travelling with and whatever your bank balance, your ultimate Leonardtown holiday is just a few clicks away with Expedia.

Top Leonardtown Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
26 Sept - 1 Oct
found 2 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
8/10 Very Good! (968 reviews)
Acceptable for my one night stay

Reviewed on 8 Aug 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
26 Sept - 1 Oct
found 2 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on 3 Aug 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
per person
26 Sept - 1 Oct
found 2 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
9.4/10 Exceptional! (1,012 reviews)
The hotel is in a great location where most areas are walkable. The rooms are comfy and stylish. The rooftop pool was very cold and I would suggest having a few more sunbeds up there.

Reviewed on 9 Aug 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
14 Oct - 21 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
8.8/10 Excellent! (1,624 reviews)
Room is basic but good enough for a short stay if you’re not staying in much. Location is convenient. Service from the staff is lacking. Overall, really good value for the price.

Reviewed on 6 Aug 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
28 Sept - 5 Oct
found 13 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Very well located. Felt safe to walk all times of day and night. Great food spots located all around. Subway not too far from it as well, only like .04 miles from it. Great staff. Will definitely stay there next time I return to D.C

Reviewed on 8 Aug 2025

Leonardtown Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
St. Marys River State Park, St. Clements Island State Park and Jefferson Patterson Park and Museum

Top hotels in Leonardtown

The Inn at Leonardtown, Ascend Hotel Collection

The Inn at Leonardtown, Ascend Hotel Collection

2.5 out of 5
41655 Park Avenue, Leonardtown, MD
Fully refundableReserve now, pay when you stay
The price is £102 per night from 31 Aug to 1 Sept
£102
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (143 reviews)
"Staff was very friendly, room was clean."

Reviewed on 8 Aug 2025

The Inn at Leonardtown, Ascend Hotel Collection
River Edge Inn

River Edge Inn

2.5 out of 5
30 Colonial Ave, Colonial Beach, VA
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (340 reviews)
"Witin walking distance to the beach and pets are acceptable."

Reviewed on 1 Aug 2025

Get rates
River Edge Inn
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is £118 per night from 1 Sept to 2 Sept
£118
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (855 reviews)
"The inn is pretty and not far from the boardwalk area in Solomons Island. It was quiet and had few guests during the midweek. The continental breakfast was good and the staff is friendly and helpful. But a few issues were odd: they had to hunt up a remote for our TV and the phone in our room lit ..."

Reviewed on 7 Aug 2025

Solomons Inn Resort & Marina
See all 548 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.
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Popular places to visit

Port of Leonardtown Winery

You can enjoy a tasting or tour at Port of Leonardtown Winery during your travels to Leonardtown. Amble around this family-friendly area's riverfront or attend a sporting event.

Port of Leonardtown Winery

Frequently asked questions

Why should I book my Leonardtown holiday with Expedia?
Choose Expedia to organise your next escape simply and all in the same place. Our top tip for getting a great deal on a Leonardtown getaway? Bundle your flights, hotel and/or car hire into a package holiday. Then throw in a couple of exciting tours and activities. Many bookings also include flexible cancellation policies, so there's no need to panic if you have to change plans. Round-the-clock help with making tweaks to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Leonardtown?
If you love the excitement that comes with peak season, head to Leonardtown in June, October and November. If you'd like a calmer vibe, January, February and August will suit you better. With average daytime temperatures of 2ºC, January is the coolest period in Leonardtown. The warmest month is July, when you can experience average temperatures of 25ºC during the day. Whatever the weather conditions, you'll find plenty of things to keep you busy here.
What is the top hotel for my holiday in Leonardtown?
Offering many of home's creature comforts, Courtyard by Marriott Baltimore Downtown/McHenry Row will make the ideal base for your Leonardtown getaway.
How do I get a cheap holiday to Leonardtown?
Our Leonardtown holidays mean plenty of savings for the savvy traveller. For the best deals, simply bundle your hotel, flights and extras (including activities). But bargain prices are only the start of your next memorable adventure. When you book with Expedia, you'll have more than 400 airlines and 321,000 hotel options around the world to pick from. No matter your style or budget, there's a holiday here just for you. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Leonardtown holiday?
Ensure your holiday in Leonardtown is an unforgettable one by checking out its top attractions. St. Marys River State Park, Sotterley Plantation, Cecils Old Mill and Port of Leonardtown Winery are some of the things worth seeing while you're here.
What is the best area to stay in when on holiday in Leonardtown?
A getaway to Leonardtown isn't complete without paying a visit to Port of Leonardtown Winery. Why not book a stay close to this fantastic tourist attraction?
Do I need a visa for my Leonardtown holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for holidays or business, will determine if you'll need a visa for Leonardtown. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your return date. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Leonardtown holiday?
Though everyone's fashion style differs, it can help to have a few guidelines for what type of clothes to wear on your holiday in Leonardtown. Consider browsing social media before you go to get inspiration for local fashion trends. Pack with confidence by checking the forecast in Leonardtown. July brings the warmest temperatures, with daily averages of 25ºC, while January days average 2ºC, making it the coolest time of the year.
What does an Expedia Leonardtown holiday include?
Flights, car hires and hotels, or any combination of them — the choice is yours. Whether you're exploring Leonardtown on a family road trip or adventuring with your friends, there's a bundle to match your style and budget. Once you've made your booking, why not add on some tours or activities? Expedia features different kinds of properties, with the most popular in Leonardtown including private holiday homes and apartments. With Expedia, you'll always enjoy the freedom and flexibility to tailor-make your holiday your way.
Does Expedia offer Book Now, Pay Later Leonardtown holidays?
Yes, we do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan best suited to your needs during checkout and take away the stress of budgeting for your trip. Make sure you bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient instalment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
  • No-deposit holidays: When you want to jump on an incredible deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.

Can I choose my airline with a Leonardtown Expedia holiday?
Most definitely. Expedia has more than 400 airline partners to pick from globally. With so much choice, finding the right carrier to bring you to Leonardtown will be easy.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.