Find hotels near Port of Leonardtown Winery, Leonardtown from AED 349

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Our top choices for Port of Leonardtown Winery hotels

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel
2.5 star property
2.4 km from Port of Leonardtown Winery
9.2 out of 10, Wonderful, (155)
"Really nice front desk staff checked us in. The hotel is very clean and comfortable and in a great location. "
United States
Robin
The price is AED 490
AED 544 total
includes taxes & fees
4 Jan - 5 January 2026
The Inn at Leonardtown, an Ascend Collection Hotel

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG
2.0 star property
11.4 km from Port of Leonardtown Winery
9.8 out of 10, Exceptional, (6)
"Excellent hotel "
United States
Edgardo
The price is AED 404
AED 448 total
includes taxes & fees
21 Dec - 22 Dec
avid hotel California - Lexington Park by IHG

Holiday Inn Express & Suites Lexington Park-California by IHG

Holiday Inn Express & Suites Lexington Park-California by IHG
2.5 star property
12.8 km from Port of Leonardtown Winery
9.2 out of 10, Wonderful, (630)
"Clean rooms and staff friendly. Would book again "
United States
Naffraz
The price is AED 466
AED 518 total
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn Express & Suites Lexington Park-California by IHG

Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park
2.5 star property
11.8 km from Port of Leonardtown Winery
9.0 out of 10, Wonderful, (57)
"I would stay again. "
United States
kendra
The price is AED 379
AED 421 total
includes taxes & fees
21 Dec - 22 Dec
Spark by Hilton California Lexington Park

Sleep Inn & Suites California MD

Sleep Inn & Suites California MD
2.5 star property
10.9 km from Port of Leonardtown Winery
8.4 out of 10, Very Good, (176)
"Excellent property "
United States
Henry
The price is AED 404
AED 448 total
includes taxes & fees
22 Dec - 23 Dec
Sleep Inn & Suites California MD

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD
2.5 star property
17.2 km from Port of Leonardtown Winery
9.2 out of 10, Wonderful, (231)
"Comfortable, quiet, clean, nice staff"
United States
Roxanne
The price is AED 467
AED 519 total
includes taxes & fees
21 Dec - 22 Dec
Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

TownePlace Suites by Marriott Lexington Park Patuxent River Naval Air Station

TownePlace Suites by Marriott Lexington Park Patuxent River Naval Air Station
3.0 star property
15.8 km from Port of Leonardtown Winery
9.0 out of 10, Wonderful, (167)
"The staff was INCREDIBLY friendly and helpful with not only dining information but general area information."
United States
Jeremy
The price is AED 584
AED 648 total
includes taxes & fees
18 Dec - 19 Dec
TownePlace Suites by Marriott Lexington Park Patuxent River Naval Air Station

Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station

Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station
2.5 star property
17.2 km from Port of Leonardtown Winery
8.6 out of 10, Excellent, (249)
"Everything was great - clean spacious room breakfast was good staff were pleasant "
United States
Theresa
The price is AED 493
AED 547 total
includes taxes & fees
18 Dec - 19 Dec
Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station

Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River
2.5 star property
17.8 km from Port of Leonardtown Winery
8.6 out of 10, Excellent, (651)
"Clean room even with the renovations going on , staff friendly breakfast was amazing . Will stay here again next year when I come to the area "
United States
Dwayne
The price is AED 387
AED 430 total
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn & Suites Lexington Park near Pax River

Hilton Garden Inn Solomons

Hilton Garden Inn Solomons
3.0 star property
18.3 km from Port of Leonardtown Winery
8.6 out of 10, Excellent, (639)
"Was a great and pleasant experience "
United States
MARLON
The price is AED 421
AED 468 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Solomons

Hampton Inn by Hilton Lexington Park

Hampton Inn by Hilton Lexington Park
2.5 star property
16.9 km from Port of Leonardtown Winery
8.2 out of 10, Very Good, (447)
"Room was very clean and bed was comfortable. Staff was pleasant and there was a decent variety for breakfast."
United States
Robert
The price is AED 379
AED 421 total
includes taxes & fees
27 Dec - 28 Dec
Hampton Inn by Hilton Lexington Park

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
3.0 star property
14.1 km from Port of Leonardtown Winery
7.6 out of 10, Good, (1004)
"Very nice staff. Clean room "
United States
William
The price is AED 325
AED 360 total
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina
2.5 star property
17.3 km from Port of Leonardtown Winery
8.0 out of 10, Very Good, (978)
"Very pleasant staff and quiet room overlooking the cove."
United States
David
The price is AED 389
AED 432 total
includes taxes & fees
17 Dec - 18 Dec
Solomons Inn Resort & Marina

Quality Inn Solomons - Beacon Marina

Quality Inn Solomons - Beacon Marina
2.5 star property
17.2 km from Port of Leonardtown Winery
7.6 out of 10, Good, (846)
"Clean comfortable room "
United States
fredrick
The price is AED 315
AED 349 total
includes taxes & fees
22 Dec - 23 Dec
Quality Inn Solomons - Beacon Marina

Extended Stay America Select Suites Lexington Park Pax River

Extended Stay America Select Suites Lexington Park Pax River
2.5 star property
17.1 km from Port of Leonardtown Winery
6.2 out of 10, (615)
"Friendly staff, room was clean."
United States
JAMES
The price is AED 324
AED 360 total
includes taxes & fees
23 Dec - 24 Dec
Extended Stay America Select Suites Lexington Park Pax River
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.

Top Port of Leonardtown Winery Hotel Reviews

Hotels near other Port of Leonardtown Winery attractions

Find out more about Port of Leonardtown Winery

Top reasons to visit Port of Leonardtown Winery

  • Delightful Wine Tastings: Experience a variety of exquisite wines with guided tastings and tours at the winery.
  • Scenic Views: Enjoy stunning vineyard vistas and breathtaking sunsets while relaxing outdoors.
  • Live Music Events: Attend lively music performances that enhance the vibrant atmosphere of the winery.
  • Outdoor Adventures: Take advantage of kayak launches and explore the beautiful surroundings of Leonardtown.
  • Community Festivals: Participate in local festivals that showcase the spirit and hospitality of the area.

Find great hotels near Port of Leonardtown Winery

Experience the charm of Leonardtown with a variety of lodging options, including pet-friendly hotels and agritourism properties. Enjoy a welcoming atmosphere for all, including LGBTQIA travelers. Many accommodations feature outdoor seating and friendly staff, ensuring a comfortable stay. Plus, you’ll be just a stone's throw away from the scenic Leonardtown Wharf, making it the perfect base for your Maryland getaway.

  • La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent: Located a mere 14.5km from Port of Leonardtown Winery, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is an excellent choice for both business travelers and vacationers seeking a pet-friendly stay. This hotel prides itself on its welcoming atmosphere and convenient amenities, which include in-room pet accommodations, making it easy for you to travel with your furry friends. Guests can enjoy a comfortable night's sleep in well-appointed rooms, and the hotel also features a business center for those who need to stay productive during their visit.
  • Extended Stay America Select Suites Lexington Park Pax River: Situated 17.7km from Port of Leonardtown Winery, Extended Stay America Select Suites Lexington Park Pax River is perfect for travelers looking for an extended stay experience. This hotel offers pet-friendly accommodations, allowing you to bring your pets along for the journey. With a focus on comfort and convenience, each suite includes a fully equipped kitchen, making it easy to prepare meals and feel at home. The friendly staff is dedicated to ensuring a pleasant stay, catering to your needs while you explore the area.
  • Spark by Hilton California Lexington Park: Just 11.3km from Port of Leonardtown Winery, Spark by Hilton California Lexington Park offers a modern and vibrant atmosphere for travelers. This hotel is pet-friendly, allowing you to share your adventures with your beloved pets. Ideal for both business and leisure travelers, Spark boasts contemporary design and a range of amenities, including a fitness center and a business area. Guests appreciate the hotel's commitment to comfort and convenience, ensuring that your stay is both enjoyable and productive.

Where to stay near Port of Leonardtown Winery

Experience the charm of Southern Maryland at Port of Leonardtown Winery, where family-friendly vibes and stunning vineyard views await. Explore local vineyards for tastings and tours, or enjoy a leisurely stroll through the picturesque landscape. Nearby, discover the friendly communities that offer recreational activities and warm hospitality. Whether you're seeking a relaxing getaway or an urban winery experience, this region is perfect for creating lasting memories with loved ones.

  • Leonardtown: Nestled in the heart of St. Mary's County, Leonardtown is a charming city where the Port of Leonardtown Winery is located. This picturesque area offers a unique blend of outdoor adventures and tranquil scenery. Visitors can enjoy activities such as motor racing and exploring the nearby recreational areas. The city's proximity to natural landmarks like lakes, rivers, and beaches makes it a haven for nature lovers. With a steady flow of travelers throughout the year, Leonardtown's peak seasons in March to April and July offer vibrant local events and stunning seasonal landscapes.
  • California: A quick 12.9km drive from Port of Leonardtown Winery, California is a dynamic city that attracts visitors seeking adventure and outdoor experiences. Known for its picturesque landscapes and recreational opportunities, California boasts notable venues for motor racing and educational pursuits. The area features landmarks such as a racetrack and historic college university, providing a mix of excitement and culture. Travel peaks from June to August, ensuring a lively summer atmosphere filled with local events and activities.
  • Solomons: Located 17.7km from the winery, Solomons is a delightful coastal city renowned for its romantic ambiance and vibrant outdoor activities. The scenic boardwalk, recreational areas, and stunning beaches draw both couples and families looking for adventure. With attractions like cliffs and an esplanade, Solomons offers breathtaking views and leisurely strolls. The city experiences moderate seasonal tourism, peaking from June to August, providing visitors with a lively atmosphere during the summer months.

Things to do near Port of Leonardtown Winery

At Port of Leonardtown Winery, visitors can enjoy delightful wine tastings and tours while soaking in the beautiful sunsets. The winery often hosts live music events, adding to the vibrant atmosphere. For the more adventurous, a kayak launch offers the chance to explore the scenic surroundings. Additionally, local festivals provide a great way to experience the community spirit and enjoy various sports activities nearby.

Shopping

Experience shopping at The Shoppes at McIntosh, just 644m from Port of Leonardtown Winery, offering a mix of city, family, and business vibes. If you're up for a drive, Wildewood Shopping Center is 11.3km away, and First Colony Shopping Center is 12.9km away, both featuring similar atmospheres.

Recreation

At Breton Bay Golf Course, enjoy a relaxing day on the green, surrounded by scenic views just 3.2km from the winery. Wicomico Shores Golf Course, located 13.2km away, offers a vibrant outdoor atmosphere. Chesapeake Hills Golf Course, 22.5km away, provides a serene setting for a refreshing golf outing.

Adventure

Experience the thrill of Budds Motorcross Speedway, located 19.3km away, where you can enjoy exhilarating motor racing. Stroll along the romantic Solomons Island Boardwalk, 17.7km away, and soak in beautiful beach views. For family fun, visit Chesapeake Beach Water Park, 45.1km away, offering exciting water adventures.

Nightlife

The nightlife in Leonardtown features the Port Tobacco Players theater, located 37.0km away, offering a charming mix of romance, entertainment, and culture. Enjoy captivating performances that bring the local arts scene to life while soaking in the vibrant atmosphere of this charming area.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Port of Leonardtown Winery

To save money on your trip to Port of Leonardtown Winery, consider visiting between December and February when accommodation prices are lower. Book your stay for a Monday, as it's typically less expensive than Saturday. Use Expedia's search tool to find budget-friendly hotels by sorting prices and filtering for eco-certified options. Additionally, combine your hotel, flights, and activities for potential package savings. Lastly, explore free activities in the area to enhance your experience without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Port of Leonardtown Winery are December to February, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Port of Leonardtown Winery is Monday. The most expensive day to stay around Port of Leonardtown Winery is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool is designed to help you find the perfect accommodation that fits your budget and preferred location. You can easily sort the results from the lowest to the highest prices, ensuring that the most affordable hotels appear at the top. Additionally, you have the option to filter your search by hotel type; for instance, if you choose the Eco-certified filter, you'll discover a selection of sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel stay at Port of Leonardtown Winery with your flights and activities when you book an Expedia package.

Find the best attractions near Port of Leonardtown Winery

When visiting Port of Leonardtown Winery in Leonardtown, Maryland, you can enjoy a variety of outdoor activities and family-friendly experiences. Explore local attractions such as Leonardtown Winery, Leonardtown Winery Park, and Leonardtown Park. Don't miss the chance to discover nearby Maryland wineries, making your trip a delightful blend of urban and natural beauty.

  • St. Mary's River State Park: Experience the beauty of nature at St. Mary's River State Park, located 9.7km from Port of Leonardtown Winery. This park offers scenic views, hiking trails, and outdoor adventure opportunities, perfect for nature enthusiasts and families looking to enjoy the great outdoors.
  • Sotterley Plantation: Visit Sotterley Plantation, situated 12.9km away, to immerse yourself in the rich history and culture of the region. This historic house showcases stunning architecture and beautiful gardens, providing a glimpse into the life of early American settlers.
  • Drum Point Lighthouse: Discover the charm of Drum Point Lighthouse, located 17.7km from the winery. This historic lighthouse offers cultural insights and stunning waterfront views, making it a perfect spot for photography and learning about maritime history.

The nearest major airports for your trip to Port of Leonardtown Winery

If you are planning a visit to Port of Leonardtown Winery, the nearest major airport is Ronald Reagan Washington National Airport (DCA), situated 69.2km away. For convenient accommodations, consider staying at the Salamander Washington DC, a luxurious 5-star hotel located 3.2km from the airport, or the Riggs Washington DC, also a 5-star option just 4.8km away. Another excellent choice is the Pendry Washington DC - The Wharf, which is 3.2km from DCA. Each of these hotels offers easy access to the airport, ensuring a smooth travel experience as you embark on your winery adventure.

Frequently asked questions

What's the area like around Port of Leonardtown Winery?
Port of Leonardtown Winery is located in a family-friendly area of Leonardtown that travelers like for its island views and riverfront. You'll find 12 hotels and other accommodations within a few miles for a convenient home base.
What's the best place to stay near Port of Leonardtown Winery?
The Inn at Leonardtown, an Ascend Collection Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and free WiFi. It's located 1.5 mi (2.4 km) from Port of Leonardtown Winery. Other good options in the area include Spark by Hilton California Lexington Park and Sleep Inn & Suites California MD.
How many hotels are there near Port of Leonardtown Winery?
Expedia has 12 hotels and other accommodations a few miles from Port of Leonardtown Winery.
If I need to cancel the hotel reservation for my stay near Port of Leonardtown Winery, will I receive a refund?
Yes, you'll find most hotel bookings are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, you may still be able to cancel and get a refund within a 24-hour period of booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review the best deals near Port of Leonardtown Winery.
Where can I learn more about changing or cancelling my trip in the area near Port of Leonardtown Winery?
To find more details about rescheduling or cancelling your stay near Port of Leonardtown Winery, go to https://www.expedia.com/service/.
What can I see and do near Port of Leonardtown Winery?
Consider spending a leisurely afternoon outside at Leonardtown Park, Abell's Wharf, or Indian Village Archeological Park. You might plan a visit to Former Rowland Property or Breton Bay Golf Course while you're in the area. If you want to see more of the surrounding area, you might plan a visit to Leonardtown Town Hall and The Shoppes at McIntosh.

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