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Leonardtown Holiday Rentals

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Holiday Rentals in Leonardtown

Tiny, Funky, and Full of Love - Welcome to the Love Shack
9.8 out of 10, Exceptional, (10)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
United States
Joleen H.
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
United States
Michelle R.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
9.8 out of 10, Exceptional, (56)
"We had a wonderful experience and stay at this cute little cottage. Hosts were amazing as well. Cottage has everything you need. Cute decor, plenty of cookware, towels, linens, TV with streaming and comfortable couch. Communication with host was outstanding and easy check-in and check-out. Will definitely stay here again and strongly recommend to others as a place to stay in the area."
United States
Mary S.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Cheery, Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (53)
"Great spot for a family of 4. Very quiet and clean."
United States
Zach H.
The price is NZ$360
includes taxes & fees
27 Oct - 28 Oct
Cheery, Peaceful Water Front Cabin on Winery Grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
United States
Travis
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront with spectacular view, close to restaurants and bars
9.8 out of 10, Exceptional, (54)
"We enjoyed our stay here! The place was incredibly clean and the view was perfect! "
United States
Rachel S.
Waterfront with spectacular view, close to restaurants and bars
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
The price is NZ$470
includes taxes & fees
20 Oct - 21 Oct
Waterfront Solomons Apartment
Waterfront Wildlife Retreat on the Patuxent River
10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
United States
Nicole V.
Waterfront Wildlife Retreat on the Patuxent River
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
9.8 out of 10, Exceptional, (76)
"The property is just as listed! Thoroughly enjoyed the house, the grounds, and the beach! Rick was accommodating and responsive. What a great place!"
United States
David and Ilana X.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (16)
"Excellent communication from the owner, Julie and the property manager. Our family (newborn to adults) stayed at this property while in town for a wedding at Rousby Hall. We were a quick and easy 15 minute drive away from the venue. The house was very clean and nicely set up to accommodate our group. We only wish we had more time to spend at the house than we did. The pictures are exactly what you see when you check in - no unhappy surprises. Thank you for hosting us and being so flexible...
United States
eileen b.
Belle of the Chesapeake Bay
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
10.0 out of 10, Exceptional, (124)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
United States
David Z.
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
The price is NZ$523
includes taxes & fees
20 Oct - 21 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
El Camino
10.0 out of 10, Exceptional, (49)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
United States
Alan B.
El Camino
3-bedroom house in charming Colonial Beach with AC, WiFi
10.0 out of 10, Exceptional, (7)
"Much more to offer that it seems. Highly recommended "
United States
Chris T.
3-bedroom house in charming Colonial Beach with AC, WiFi
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (80)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
9.8 out of 10, Exceptional, (11)
"From the time we arrived, we were enjoying the beautiful view. The host really made our stay wonderful as the home is set up with everything you need and then some extras. We really enjoyed the kayaks and paddle board during the day and brought along some floats for a little relaxation in the water. After dinner, we enjoyed the hot tub and beautiful sunset. We all left there well rested and wanting to come back soon. It was the perfect get away to kick off summer."
United States
LeAnn C.
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
9.8 out of 10, Exceptional, (19)
"Very clean, great location, and comfortable beds, we had a great time. Walking distance to bars, restaurants, and coffee shops. Very convenient, and the owner was easy to work with. "
United States
Jim P.
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (3)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is NZ$640
includes taxes & fees
20 Oct - 21 Oct
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (59)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
United States
Whitney H.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (45)
"We thoroughly enjoyed our stay. Thank you! "
United States
Cerkez C.
Cozy Virginia Potomac Riverfront Cottage
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

Find out more about Leonardtown

Everything you need to know about Leonardtown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Leonardtown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leonardtown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Leonardtown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leonardtown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leonardtown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leonardtown holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Leonardtown rentals

At Expedia, we put the best Leonardtown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leonardtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leonardtown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leonardtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Waterfront with spectacular view, close to restaurants and bars: This holiday home rental outside of Leonardtown is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.