Search Hotels Near Port of Leonardtown Winery, Leonardtown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Port of Leonardtown Winery hotels

Lobby
The Inn at Leonardtown, an Ascend Collection Hotel

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, (156)
"Love this hotel, we always stay here when we visit family. Very nice, clean, safe and you can walk to many shops and restaurants. "
United States
April
The price is ฿4,279
฿4,749 total
includes taxes & fees
25 Jan - 26 Jan 2026
The Inn at Leonardtown, an Ascend Collection Hotel
Free daily buffet breakfast
avid hotel California - Lexington Park by IHG

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, (8)
"Excellent hotel "
United States
Edgardo
The price is ฿3,482
฿3,864 total
includes taxes & fees
4 Jan - 5 Jan 2026
avid hotel California - Lexington Park by IHG
Lobby
Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park
2.5 star property
11.8 km from Port of Leonardtown Winery
9.2 out of 10, Wonderful, (61)
"I would stay again. "
United States
kendra
The price is ฿3,537
฿3,926 total
includes taxes & fees
6 Jan - 7 Jan 2026
Spark by Hilton California Lexington Park
Exterior
Holiday Inn Express & Suites Lexington Park-California 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, (633)
"Everything was excellent "
United States
Kirstie
The price is ฿4,399
฿4,883 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express & Suites Lexington Park-California by IHG
Terrace/patio
Home2 Suites by Hilton Lexington Park Patuxent River NAS, 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, (233)
"Comfortable, quiet, clean, nice staff"
United States
Roxanne
The price is ฿4,542
฿5,041 total
includes taxes & fees
15 Jan - 16 Jan 2026
Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD
Reception
Sleep Inn & Suites California MD

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, (178)
"Excellent property "
United States
Henry
The price is ฿3,879
฿4,306 total
includes taxes & fees
25 Jan - 26 Jan 2026
Sleep Inn & Suites California MD
Lobby
Comfort Inn & Suites Lexington Park near Pax River

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, (653)
"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 ฿3,291
฿3,653 total
includes taxes & fees
6 Jan - 7 Jan 2026
Comfort Inn & Suites Lexington Park near Pax River
Exterior
Fairfield Inn 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 ฿4,162
฿4,620 total
includes taxes & fees
31 Dec - 1 Jan 2026
Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station
Exterior
Hilton Garden Inn Solomons

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, (641)
"Was a great and pleasant experience "
United States
MARLON
The price is ฿3,561
฿3,952 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hilton Garden Inn Solomons
Lobby sitting area
Hampton Inn by Hilton Lexington Park

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, (450)
"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 ฿3,003
฿3,333 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn by Hilton Lexington Park
Exterior
Solomons Inn Resort & Marina

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, (984)
"Very pleasant staff and quiet room overlooking the cove."
United States
David
The price is ฿3,324
฿3,690 total
includes taxes & fees
6 Jan - 7 Jan 2026
Solomons Inn Resort & Marina
Lobby sitting area
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

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, (1003)
"Staff very friendly,, room was very nice and clean, good location for business I was in town for"
United States
Michael
The price is ฿2,798
฿3,106 total
includes taxes & fees
2 Jan - 3 Jan 2026
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
BBQ/picnic Area
Quality Inn Solomons - Beacon 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, (849)
"The room was very nice and great friendly staff, very nice peaceful area!"
United States
Matthew
The price is ฿2,717
฿3,016 total
includes taxes & fees
29 Jan - 30 Jan 2026
Quality Inn Solomons - Beacon Marina
Property amenity
Extended Stay America Select Suites Lexington Park Pax River

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 ฿2,848
฿3,162 total
includes taxes & fees
31 Dec - 1 Jan 2026
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.
View all properties

Top Port of Leonardtown Winery Hotel Reviews

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"The staff was very friendly and helpful checking in and out. They were able to answer any questions I had and provided wonderful feedback. They property is very convenient to some shops and a short walk to the island. "
Michelle 1-night trip
Posted 2 weeks ago
Solomons Inn Resort & Marina
SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick

10/10 Excellent
"The room was very clean. The staff was super friendly."
Sherri 1-night trip
Posted 3 weeks ago
SureStay by Best Western Prince Frederick

Hotels near other Port of Leonardtown Winery attractions

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.
See properties

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.
See properties

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 12 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 La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent and Spark by Hilton California Lexington Park.
How many hotels will I find near Port of Leonardtown Winery?
Expedia has 12 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?
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.