Hotels near Port of Leonardtown Winery Leonardtown

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May 11 - May 12
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May 16 - May 18
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May 23 - May 25

Where to stay near Port of Leonardtown Winery?

The Inn at Leonardtown, Ascend Hotel Collection
Lobby

The Inn at Leonardtown, Ascend Hotel Collection

2.5 star property
9.2 out of 10, Wonderful, (132)
$123 nightly
The price is $137
Jun 8 - Jun 9
Total includes taxes and fees
The Inn at Leonardtown, Ascend Hotel Collection
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.

Other landmarks in Leonardtown

New Towne Neck State Park

New Towne Neck State Park is 5.3 mi (8.6 km) from central Leonardtown, why not stop by during your stay.

See properties in New Towne Neck State Park
New Towne Neck State Park
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

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Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What are the best hotels near Port of Leonardtown Winery?
How much does it cost to stay in a hotel near Port of Leonardtown Winery?
You can find different room prices based on when and where you want to go. Simply sort by price on the search results and filter by your preferred criteria to find the best options for you and your budget.
  • Take a look at the lowest price per night $84 total
What cheap hotels are close to Port of Leonardtown Winery?
Can I find hotels close to Port of Leonardtown Winery that are fully refundable?
Yes, you’ll find hotels with refundable room rates, but be sure to check the cancellation deadline before you book. To find refundable rates, use the “Fully refundable” filter when you search for hotels.
What are the best romantic hotels near Port of Leonardtown Winery?
What are the best hotels close to Port of Leonardtown Winery with free breakfast?
Which hotels near Port of Leonardtown Winery have rooms with great views?
What are the best family hotels close to Port of Leonardtown Winery?
What are the best luxury hotels near Port of Leonardtown Winery?
  • Treat yourself when you stay at Swanendele Inn at St. Mary’s Maryland, which is within reach of Port of Leonardtown Winery and offers a beach, a free cooked-to-order breakfast, and proposal/romance packages.
What are the best hotels near Port of Leonardtown Winery with free parking?
What are the best hotels near Port of Leonardtown Winery with a pool?
What cheap motels can I book close to Port of Leonardtown Winery?
  • To stay economically near Port of Leonardtown Winery, you can book Pax River Hotel, which offers parking and a gym.
  • Washington & Lee Motel is another affordable motel to consider in the area.
What are the best things to see and do around my hotel near Port of Leonardtown Winery?
  • You can check out sights near Port of Leonardtown Winery like Maryland International Raceway, Calvert Cliffs State Park, and St. Mary’s College of Maryland.
  • Other places in the area are Westmoreland State Park, Breezy Point Beach, and Budds Motorcross Speedway.

Terms and conditions

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