The Best Hotels Closest to Port of Leonardtown Winery in Leonardtown - 2026 Updated Prices

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Our top choices for Port of Leonardtown Winery hotels

A spacious lobby with a reception desk, seating area, and large windows.

A hotel room with a blue sofa, a desk with a chair, a flat-screen TV, a lamp, a coffee maker, and a framed artwork on the wall.

A brick building with large windows and a sign for The Inn at Park Avenue Hotel.

A modern hotel lobby with a bar area, seating arrangements, and a television.

1. The Inn at Leonardtown, an Ascend Collection Hotel

2.4 km from Port of Leonardtown Winery

"The room was spacious and exceptionally clean. There is ample and convenient parking as well. Everyone on the staff was very friendly and helpful. The Inn is right downtown adjacent to the square and all the restaurants and shops, and just a short walk to the Waterfront park. We make regular trips to Southern Maryland to visit family, but this is our first time staying in Leonardtown. We will definitely be returning to The Inn at Leonardtown."

Thurl

Rp2.655.868

Rp2.948.013 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel with a prominent 'avid' sign, large windows, and a covered outdoor seating area.

A modern living room with a sectional sofa, a coffee table, and a flat-screen TV mounted on a teal accent wall.

A gym with treadmills, dumbbells, a bench, and exercise balls.

A modern reception area with a counter, a 'Market' sign, and a refrigerated display case with beverages.

2. avid hotel California - Lexington Park by IHG

11.4 km from Port of Leonardtown Winery

Eileen

Rp1.728.346

Rp1.918.464 total

includes taxes & fees

12 Oct - 13 Oct

A hotel lobby with a reception desk, a staircase, seating area, and a flat-screen TV.

A modern dining area with multiple tables and chairs, a kitchen counter, and a large window providing natural light.

A swimming pool with chairs and a changing room.

3. Spark by Hilton California Lexington Park

11.8 km from Port of Leonardtown Winery

Rocio

Rp2.177.003

Rp2.416.473 total

includes taxes & fees

2 Oct - 3 Oct

An indoor swimming pool with clear water, surrounded by lounge chairs and a lifeguard station.

A hotel room with two beds, a blue sofa, a desk, and a TV.

A multi-story building with a mix of brick and stone facades, large windows, and a covered entrance area.

A hotel room with a blue sofa, a wooden desk, a black office chair, a standing lamp, and a large window with curtains.

4. Holiday Inn Express & Suites Lexington Park-California by IHG

12.8 km from Port of Leonardtown Winery

Nadia

Rp2.547.974

Rp2.828.252 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large bed, a nightstand with a lamp, a brown sofa, and artwork on the wall.

A living room with a sofa, two chairs, a staircase, a large window, and a bookshelf.

A reception area with a wooden reception desk, a clock, and a plant.

A small, clean room with a white table and four chairs, a refrigerator, a coffee maker, and a shelf with various items.

5. Sleep Inn & Suites California MD

10.9 km from Port of Leonardtown Winery

Taylor

Rp1.552.780

Rp1.723.586 total

includes taxes & fees

6 Oct - 7 Oct

An outdoor seating area with a fire pit, cushioned benches, and a modern design.

A hotel with a modern design, featuring a prominent 'HOME 2' sign, a covered entrance, and a parking lot.

A cozy outdoor seating area with a stone fire pit, wicker ottomans, and a red stool.

6. Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

17.2 km from Port of Leonardtown Winery

Caroline

Rp2.556.255

Rp2.837.443 total

includes taxes & fees

11 Oct - 12 Oct

A reception area with a round wooden table, a potted plant, a vase with dried flowers, a clock, and a reception desk.

A spacious lobby with a stone fireplace, blue seating, and a television mounted on the wall.

A hotel room with a bed, a sofa, a desk, and a TV.

7. Comfort Inn & Suites Lexington Park near Pax River

17.8 km from Port of Leonardtown Winery

Jennifer

Rp2.058.335

Rp2.284.753 total

includes taxes & fees

25 Oct - 26 Oct

A covered outdoor seating area with wicker furniture and large windows.

A modern living room with a fireplace, sofas, and a large window.

A spacious hotel lobby with multiple seating areas, large windows offering views of the outdoors, and a modern interior design.

A hotel lobby with a fireplace, a reception desk, and a seating area.

8. Hilton Garden Inn Solomons

18.3 km from Port of Leonardtown Winery

Aaron

Rp2.188.977

Rp2.429.765 total

includes taxes & fees

25 Oct - 26 Oct

A hotel lobby with a dining area, seating, a fireplace, and a view of the outside through large windows.

A reception desk with a 'Welcome to the Crab State' sign, two HP laptops, and a 'No Mask, No Service' sign.

A living room with a stone wall, a fireplace, and framed pictures.

A hotel room with a bed, a desk with a chair, a television, and a wardrobe.

9. Hampton Inn by Hilton Lexington Park

16.9 km from Port of Leonardtown Winery

Edwin

Rp1.884.788

Rp2.092.116 total

includes taxes & fees

12 Oct - 13 Oct

A modern hotel lobby with seating areas, a reception desk, and a staircase.

A modern living room with a sectional sofa, a wooden coffee table, a framed abstract painting, a window with blue curtains, and a wall-mounted air conditioner.

A modern waiting area with a sofa, two round tables, a decorative wall, and a ceiling light fixture.

10. La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

14.1 km from Port of Leonardtown Winery

LORRIE JONES

Rp1.659.917

Rp1.842.508 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a living area, dining table, kitchenette, and a TV.

An outdoor patio with brick flooring, red umbrellas, and metal chairs.

A hotel room with a sofa, armchair, and a bed.

A hotel room with a bed, a sofa, a desk, a chair, a television, and a kitchenette.

11. TownePlace Suites by Marriott Lexington Park Patuxent River Naval Air Station

15.8 km from Port of Leonardtown Winery

Steffan

Rp3.027.804

Rp3.360.862 total

includes taxes & fees

18 Oct - 19 Oct

A Fairfield by Marriott Inn & Suites building with a covered entrance, multiple windows, and a parking lot.

A modern dining area with a wooden table and chairs, a kitchen counter with various appliances, and a colorful mural on the wall.

A gym with treadmills, weight machines, and a rack of dumbbells.

An outdoor patio with tables and chairs, blue umbrellas, and air conditioning units on the building facade.

12. Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station

17.2 km from Port of Leonardtown Winery

Michael

Rp2.725.024

Rp3.024.776 total

includes taxes & fees

27 Sept - 28 Sept

A hotel room with a large bed, a separate bathroom with a bathtub, and a mirror above the sink.

A hotel room with a sofa, two chairs, a desk with a computer, a TV mounted on the wall, a window with blinds, and a potted plant.

A swimming pool with lounge chairs, a wooden planter, and a white fence.

A clean, modern kitchen area with a microwave, coffee maker, and a pastry display.

13. Quality Inn Solomons - Beacon Marina

17.3 km from Port of Leonardtown Winery

Tamara

Rp1.812.091

Rp2.011.421 total

includes taxes & fees

12 Oct - 13 Oct

A hotel room with a bed, desk, chair, TV, and artwork.

A hotel laundry room with two Whirlpool washers and dryers, a soap and bleach dispenser, and a sign indicating the first floor and guest laundry area.

A room with two armchairs, a large potted plant, a framed California map, and a large window.

A hotel corridor with a vending machine, a refrigerator, and a fire alarm.

14. Super 8 by Wyndham Lexington Park/California Area

14 km from Port of Leonardtown Winery

Lazarus

Rp1.499.385

Rp1.664.379 total

includes taxes & fees

2 Oct - 3 Oct

A living room with a large window, a sofa, two armchairs, a coffee table, and a TV on a stand.

A modern kitchen with white cabinets, a microwave, a refrigerator, a sink, and a wall-mounted light.

A hotel with a sign indicating it is part of the extended Stay America network.

15. Extended Stay America Select Suites Lexington Park Pax River

17.1 km from Port of Leonardtown Winery

David

Rp1.769.922

Rp1.964.614 total

includes taxes & fees

9 Oct - 10 Oct

A single-story house with a front porch, a small deck, and a number '4' on the side.

A beach with a wooden pier extending into the water, a picnic table, and a clear sky.

A beach with several Adirondack chairs arranged in a semi-circle facing the water.

A marina with docked boats, a covered structure, and a small building in the background.

16. Coles Point Marina

18.3 km from Port of Leonardtown Winery

Rp2.457.387

Rp4.321.446 total

includes taxes & fees

7 Oct - 8 Oct

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Compare popular hotels close to Port of Leonardtown Winery

Property	Property class	Guest rating
The Inn at Leonardtown, an Ascend Collection Hotel	9.4 Exceptional 190 reviews	View
avid hotel California - Lexington Park by IHG	9.4 Exceptional 206 reviews	View
Spark by Hilton California Lexington Park	9.0 Wonderful 121 reviews	View
Holiday Inn Express & Suites Lexington Park-California by IHG	9.2 Wonderful 694 reviews	View
Sleep Inn & Suites California MD	8.4 Very good 230 reviews	View

Top Port of Leonardtown Winery Hotel Reviews

River Edge Inn

8/10 Good

"Nice clean place located very near bars and restaurant. Several beach areas."

The Inn at Leonardtown, an Ascend Collection Hotel

8/10 Good

"Welcoming staff, excellently situated in Downtown Leonardtown, decent offering of complimentary breakfast, including pre-made filled croissants. Only issue was my initial room suffered from external noise issues, suspected to be from the hotels air conditioning system (not the room), however the staff were more than happy to move me to another room which was much quieter."

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent

"Our room was extremely clean. The breakfast are was also clean and bright. The internet connection was spotty and very slow."

Holiday Inn Express & Suites Lexington Park-California by IHG

10/10 Excellent

"The place was very nice and clean. Staff was nice and friendly"

avid hotel California - Lexington Park by IHG

10/10 Excellent

"Brand new hotel, in a great part of town with easy access to many restaurants and stores. The front desk staff and cleaning staff were so polite & friendly. My room was exceptionally clean and smelled amazing. I appreciate the personal welcome on the TV as I entered the room and whenever I turned the TV on. Plenty of free shampoo, conditioner, body wash, hand soap, and lotion provided at no extra cost, mo more mini bottles or thin bars of soap, all Dove products! As a solo female traveler I felt safe at all times. Plenty of USB charging ports in the room. Thank you for a wonderful and comforting stay while in town for my brother’s wedding and visiting family & friends."

Historic 1825 Chesapeake Farm Stay

10/10 Excellent

"Holly and Jay were friendly hosts. The farmhouse was clean and comfortable. The breakfast was very yummy. We only stayed one night, but next time we will definitely spend more time there. If you are down near calvert cliffs/flag ponds, the farmhouse was only about 10 minutes to flag ponds."

Springhill Suites by Marriott Prince Frederick

8/10 Good

"The property was ok. The room was clean and served its purpose. They do offer free breakfast. I would not call what I had breakfast. Cold eggs and a stale muffin. So for the price you it was not worth it."

Hilton Garden Inn Solomons

8/10 Good

"No Continental Breakfast ! No 24/7 Coffee Bar ! And Pay for Parking is No Way to greet your customers !!"

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

Other attractions near Port of Leonardtown Winery

The Shoppes at McIntosh

You can do some window-shopping at The Shoppes at McIntosh during your trip to Leonardtown. Take in the festivals and sunsets in the area.

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Leonard's Grant Recreation Area

After visiting Leonard's Grant Recreation Area, make a plan to see the other sights and activities in Leonardtown. Take in the festivals and sunsets in the area.

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Leonardtown Park

Explore the great outdoors at Leonardtown Park, a lovely green space in Leonardtown. Take in the festivals and sunsets in the area.

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Leonard's Grant Community Area

Leonard's Grant Community Area is just one of the places to see in Leonardtown, so why not enjoy the other things to explore during your travels? Take in the festivals and sunsets in the area.

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Leonardtown Library

Leonardtown Library is just one of the places to see in Leonardtown, so why not enjoy the other things to explore during your travels? Take in the festivals and sunsets in the area.

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Miedzinski Park

After visiting Miedzinski Park, make a plan to see the other sights and activities in Leonardtown. Take in the festivals and sunsets in the area.

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College of Southern Maryland - Leonardtown Campus

Enjoy the student vibe at College of Southern Maryland - Leonardtown Campus as part of your travels around Leonardtown. Take in the festivals and sunsets in the area.

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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 travellers like for its island views and riverfront. You'll find 11 hotels and other accommodations within a few miles for a convenient home base.

Where is 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 traveller 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 avid hotel California - Lexington Park by IHG and La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent.

How many hotels will I find near Port of Leonardtown Winery?

Expedia has 11 hotels and other accommodation options 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! Most hotel bookings are refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Add dates, click "Search", then use the filter option "fully refundable" to get top deals close to Port of Leonardtown Winery.

What can I see and do near Port of Leonardtown Winery?

Get outside and spend some time strolling around Abell's Wharf, Leonardtown Park and Indian Village Archeological Park. Create some family memories at St. Mary's County Arts Council and Saint Mary's Fairground. Breton Bay Golf Course and Leonardtown Town Hall are both worth a visit while you're out exploring.

Search Hotels Near Port of Leonardtown Winery, Leonardtown

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Port of Leonardtown Winery hotels

1. The Inn at Leonardtown, an Ascend Collection Hotel

2. avid hotel California - Lexington Park by IHG

3. Spark by Hilton California Lexington Park

4. Holiday Inn Express & Suites Lexington Park-California by IHG

5. Sleep Inn & Suites California MD

6. Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

7. Comfort Inn & Suites Lexington Park near Pax River

8. Hilton Garden Inn Solomons

9. Hampton Inn by Hilton Lexington Park

10. La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

11. TownePlace Suites by Marriott Lexington Park Patuxent River Naval Air Station

12. Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station

13. Quality Inn Solomons - Beacon Marina

14. Super 8 by Wyndham Lexington Park/California Area

15. Extended Stay America Select Suites Lexington Park Pax River

16. Coles Point Marina

Compare popular hotels close to Port of Leonardtown Winery

Top Port of Leonardtown Winery Hotel Reviews

River Edge Inn

The Inn at Leonardtown, an Ascend Collection Hotel

Comfort Inn & Suites Lexington Park near Pax River

Holiday Inn Express & Suites Lexington Park-California by IHG

avid hotel California - Lexington Park by IHG

Historic 1825 Chesapeake Farm Stay

Springhill Suites by Marriott Prince Frederick

Hilton Garden Inn Solomons

Quality Inn Solomons - Beacon Marina

Other attractions near Port of Leonardtown Winery

The Shoppes at McIntosh

Leonard's Grant Recreation Area

Leonardtown Park

Leonard's Grant Community Area

Leonardtown Library

Miedzinski Park

College of Southern Maryland - Leonardtown Campus

Frequently asked questions