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Holiday Rentals in Leonardtown

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Holiday Rentals in Leonardtown

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

Piney Point
10.0 out of 10, Exceptional, (13)
"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."
United States
Dawn B.
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons
9.6 out of 10, Exceptional, (7)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
The price is €476
includes taxes & fees
18 Nov - 19 Nov
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

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

Port Republic
10.0 out of 10, Exceptional, (180)
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and...
United States
Vicki K.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Nice little place to stay"
United States
Eric S.
The price is €243
includes taxes & fees
18 Nov - 19 Nov
Peaceful Waterfront Apartment in the Heart of Solomons Island

Cheery, Peaceful Water Front Cabin on Winery Grounds

Colonial Beach
9.8 out of 10, Exceptional, (56)
"Great spot for a family of 4. Very quiet and clean."
United States
Zach H.
The price is €187
includes taxes & fees
19 Nov - 20 Nov
Cheery, Peaceful Water Front Cabin on Winery Grounds

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Tall Timbers
9.8 out of 10, Exceptional, (58)
"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

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Drayden
9.8 out of 10, Exceptional, (77)
"Host was gracious. house is well prepared and clean. "
United States
Mark A.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek
10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

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

Port Republic
10.0 out of 10, Exceptional, (123)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (37)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is €251
includes taxes & fees
18 Nov - 19 Nov
Soul Oasis - home on the Chesapeake Bay

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

Newburg
9.8 out of 10, Exceptional, (154)
"Lovely place and location!"
United States
Christa W.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Lottsburg
9.8 out of 10, Exceptional, (11)
"Most amazing views. Owners are very responsive and made sure we had a wonderful stay. Very family friendly!"
United States
Diane C.
Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Discover tranquility near Calvert Cliffs

Saint Leonard
9.8 out of 10, Exceptional, (18)
"Comfortable beds, large house with awesome views…had a great experience"
United States
Deborah R.
Discover tranquility near Calvert Cliffs

Waterfront with spectacular view, close to restaurants and bars

Colonial Beach
9.8 out of 10, Exceptional, (58)
"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

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Lusby
9.6 out of 10, Exceptional, (5)
"So communicative and thoughtful- helpful throughout and it’s a wonderful house stocked with everything we’d want. Thank you!!"
United States
Elizabeth S.
Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Colonial Beach
9.8 out of 10, Exceptional, (19)
"So convenient to the beach and downtown Colonial Beach restaurants and shopping. We will definitely be back! "
United States
Marisa Z.
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach
10.0 out of 10, Exceptional, (82)
"This was my 3 stay at Shannon's beautiful home. My family, friends and I equally adore the home, the serene surroundings and Shannon's hospitality. I completely recommend this property 10 out of 10!"
United States
Teshara C.
Inviting and Serene Home on Monroe Bay Creek

Cozy Virginia Potomac Riverfront Cottage

Hague
9.6 out of 10, Exceptional, (45)
"Wonderful views, clean home and quaint ! We highly recommend!"
United States
Tim R.
Cozy Virginia Potomac Riverfront Cottage

Luxurious 3 Bedroom Riverfront Condo with Private Deck

2.0 star property
Colonial Beach
10.0 out of 10, Exceptional, (13)
"Beautiful place and very clean will be going back next uear"
United States
Connie S.
Luxurious 3 Bedroom Riverfront Condo with Private Deck

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

Lusby
10.0 out of 10, Exceptional, (62)
"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
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, apart-hotels, 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 €187 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?

Belle of the Chesapeake Bay: This holiday home rental outside of Leonardtown offers a patio, an arcade/games room and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 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?

Abell's Wharf and St. Mary's River State Park are a couple of lovely local spots to get outside and enjoy nature. While here, Leonardtown Town Hall and Breton Bay Golf Course 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.