Hotels near Port of Leonardtown Winery Leonardtown

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Apr 25 - Apr 26
Tomorrow
Apr 26 - Apr 27
This weekend
Apr 25 - Apr 27
Next weekend
May 2 - May 4

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, (130)
The price is $137
includes taxes & fees
$123 per night
May 18 - May 19
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.

Summer Getaway Sale

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*
Sign in or join for free

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 $86
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 a gym and parking.
  • 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, St. Mary’s College of Maryland, and Calvert Cliffs State Park.
  • Other places in the area are Westmoreland State Park, Breezy Point Beach, and Budds Motorcross Speedway.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

https://www.hotels.com/lp/b/deals