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Top Holiday Rentals in Leonardtown

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (177)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (51)
"Great stay and peaceful spot. "
The price is £191
includes taxes & fees
27 Aug - 28 Aug
Cheery, Peaceful Water Front Cabin on Winery Grounds

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (140)
"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (41)
"Everything was great. "
Waterfront with spectacular view, close to restaurants and bars

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (51)
"Wonderful golf cart community! Perfect way to relax, short walk to the water in either direction. Meet allot of the locals, enjoyed the local breweries and restuarants."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Tiny, Funky, and Full of Love - Welcome to the Love Shack

10.0 out of 10, Exceptional, (4)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (120)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock

Sail Away

10.0 out of 10, Exceptional, (4)
"Loved the View from inside the condo and on the balcony. Has everything you need and is new and clean. Right on the boardwalk with beach and res"
The price is £229
includes taxes & fees
14 Aug - 15 Aug
Sail Away

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (31)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

10.0 out of 10, Exceptional, (55)
"All around very clean, quiet and enjoyable place to stay."
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (10)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is £220
includes taxes & fees
5 Sept - 6 Sept
Waterfront Solomons Apartment

Waterfront 3-Bed Oasis Perfect for City Getaway

10.0 out of 10, Exceptional, (11)
"We came to the area to participate a disc golf tournament at Lake Marshall. The location was perfect. We had a great time cooking over the fire, making s'mores, and checking out Montross and Colonial Beach. I highly recommend staying at this property. "
Waterfront 3-Bed Oasis Perfect for City Getaway

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (16)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway

Where peace is sitting by the moonlight

9.6 out of 10, Exceptional, (92)
"Amazing home with a great view. "
Where peace is sitting by the moonlight

Charming 3-bedroom house with WiFi, AC in delightful Colonial Beach

10.0 out of 10, Exceptional, (7)
"Host provided everything needed and very responsive. Truly enjoyed our stay and the area. "
Charming 3-bedroom house with WiFi, AC in delightful Colonial Beach
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.
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Top Leonardtown Hotel Reviews

Frequently asked questions

Are there holiday rentals in Leonardtown?

Yes, there are holiday rentals in Leonardtown close to Saint Mary's Fairground, or you can select a more secluded option if you're looking for a relaxing stay. Leonardtown is known for its seafood restaurants and festivals. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best holiday rentals that Leonardtown has to offer?

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: This holiday home rental outside of Leonardtown is located on a lake, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Leonardtown?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Leonardtown stay.

What’s there to see and do in Leonardtown?

St. Mary's River State Park and Leonardtown Park are a couple of lovely local spots to get outside and enjoy nature. While here, Port of Leonardtown Winery and Leonardtown Town Hall are other places worth a visit.

What’s a holiday rental in Leonardtown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leonardtown. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.