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Holiday Rentals in Leonardtown

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Holiday Rentals in Leonardtown

Anne & Fred`s Leonardtown Home W/ Arcade room!

Leonardtown
9.2 out of 10, Wonderful, (5)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
The price is €511
includes taxes & fees
1 Dec - 2 Dec
Anne & Fred`s Leonardtown Home W/ Arcade room!

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

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Port Republic
9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
The price is €156
includes taxes & fees
5 Dec - 6 Dec
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

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

4-BR Waterfront Turret Home

2.0 star property
Solomons
10.0 out of 10, Exceptional, (7)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
United States
Rudy L.
The price is €649
includes taxes & fees
1 Dec - 2 Dec
4-BR Waterfront Turret Home

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Point Lookout
9.4 out of 10, Exceptional, (8)
"The house was close to family in the area, so location was great. The house was clean and airy. The door lock was a bit tricky - otherwise all was excellent."
United States
Marc C.
The price is €296
includes taxes & fees
30 Nov - 1 Dec
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

3.0 star property
Lusby
The price is €625
includes taxes & fees
1 Dec - 2 Dec
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks

Cottage Located on the Patuxent River!

Prince Frederick
10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is €280
includes taxes & fees
18 Nov - 19 Nov
Cottage Located on the Patuxent River!

Sail Away

Colonial Beach
9.8 out of 10, Exceptional, (8)
"Very clean and well kept. Pictures were accurate. I would stay here again. "
United States
Anne
The price is €256
includes taxes & fees
18 Nov - 19 Nov
Sail Away

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict
9.0 out of 10, Wonderful, (6)
"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 €264
includes taxes & fees
18 Nov - 19 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Waterfront home where you can relax or enjoy the things the Northern Neck.

Lottsburg
10.0 out of 10, Exceptional, (11)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
The price is €267
includes taxes & fees
18 Nov - 19 Nov
Waterfront home where you can relax or enjoy the things the Northern Neck.

Charming Waterfront 3-bedroom house in Piney Point

Piney Point
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is €508
includes taxes & fees
18 Nov - 19 Nov
Charming Waterfront 3-bedroom house in Piney Point

Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

Lusby
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €704
includes taxes & fees
18 Nov - 19 Nov
Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

River Refresh - Waterfront with Spa on Placid Bay

Colonial Beach
10.0 out of 10, Exceptional, (20)
"Spectacular place, fenomenal view, peaceful and quiet on fall season. We’re definitely coming back. Highly recommend. "
United States
Joyce
The price is €459
includes taxes & fees
18 Dec - 19 Dec
River Refresh - Waterfront with Spa on Placid Bay

Game Themed Fun! Boats+Beach+King Bd+EV Chrgr

Montross
10.0 out of 10, Exceptional, (29)
"Comfy, relaxing, beautiful, relaxing vacation home. We went to unwind and the facilities and owners were a delight. Kitchen was super well stocked with everything needed to handle meals for 11 people. Popcorn was a smash. The front door unlocked with our code and we were all ready to expand and kick off 9 days together."
United States
Al F.
The price is €442
includes taxes & fees
1 Dec - 2 Dec
Game Themed Fun! Boats+Beach+King Bd+EV Chrgr

Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Colonial Beach
9.8 out of 10, Exceptional, (15)
"We love going to Colonial Beach. This house offered everything we were looking for in a mini vacation."
United States
Anonymous traveller
The price is €421
includes taxes & fees
30 Nov - 1 Dec
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Montross
10.0 out of 10, Exceptional, (4)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

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

Luxury Modern Waterfront Retreat

Montross
9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is €437
includes taxes & fees
1 Dec - 2 Dec
Luxury Modern Waterfront Retreat

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Lexington Park
10.0 out of 10, Exceptional, (5)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
United States
Lisa M.
The price is €322
includes taxes & fees
18 Nov - 19 Nov
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
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.