Leonardtown Holiday Rentals

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Holiday Rentals in Leonardtown

Apartment in 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 AU$895
includes taxes & fees
3 Dec - 4 Dec
Anne & Fred`s Leonardtown Home W/ Arcade room!

Cabin in Colonial Beach

9.8 out of 10, Exceptional, (56)
"Very quiet and great location."
United States
Cindy B.
The price is AU$287
includes taxes & fees
3 Dec - 4 Dec
Cheery, Peaceful Water Front Cabin on Winery Grounds

Apartment in Port Republic

9.4 out of 10, Exceptional, (6)
"Great place to stay"
United States
Sherry R.
The price is AU$273
includes taxes & fees
5 Dec - 6 Dec
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Cottage in Lusby

9.8 out of 10, Exceptional, (38)
"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 AU$439
includes taxes & fees
10 Dec - 11 Dec
Soul Oasis - home on the Chesapeake Bay

Cottage in 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 AU$547
includes taxes & fees
3 Dec - 4 Dec
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Holiday Home in Solomons

2.0 star property
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 AU$1,045
includes taxes & fees
14 Dec - 15 Dec
4-BR Waterfront Turret Home

Cottage in Benedict

9.2 out of 10, Wonderful, (7)
"The owner was very nice "
United States
karen
The price is AU$462
includes taxes & fees
10 Dec - 11 Dec
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Holiday Home in 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 AU$467
includes taxes & fees
3 Dec - 4 Dec
Waterfront home where you can relax or enjoy the things the Northern Neck.

Apartment in Colonial Beach

9.8 out of 10, Exceptional, (9)
"Very clean and well kept. Pictures were accurate. I would stay here again. "
United States
Anne
The price is AU$452
includes taxes & fees
8 Dec - 9 Dec
Sail Away

Cottage in 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 AU$490
includes taxes & fees
3 Dec - 4 Dec
Cottage Located on the Patuxent River!

Cottage in Lusby

3.0 star property
The price is AU$1,175
includes taxes & fees
2 Jan - 3 Jan 2026
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Holiday Home in Montross

9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is AU$743
includes taxes & fees
3 Dec - 4 Dec
Luxury Modern Waterfront Retreat

Holiday Home in Point Lookout

9.6 out of 10, Exceptional, (155)
"Nice place to stay and very enjoyable environment. Management team is excellent to handle the property. "
United States
william s.
The price is AU$525
includes taxes & fees
3 Dec - 4 Dec
Kentigern Shed at Scotland Yards

Holiday Home in Prince Frederick

9.6 out of 10, Exceptional, (4)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AU$563
includes taxes & fees
3 Dec - 4 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Lusby

10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Holiday Home in 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 AU$712
includes taxes & fees
7 Dec - 8 Dec
Game Themed Fun! Boats+Beach+King Bd+EV Chrgr

Holiday Home in 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 AU$885
includes taxes & fees
3 Dec - 4 Dec
Charming Waterfront 3-bedroom house in Piney Point

Holiday Home in Solomons

9.6 out of 10, Exceptional, (8)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Holiday Home in Prince Frederick

10.0 out of 10, Exceptional, (8)
"Clean and easy "
United States
Robert R.
The price is AU$609
includes taxes & fees
3 Dec - 4 Dec
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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 favourite 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 depend 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 AU$287 per night. Entering your travel dates in the search wizard might find you 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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This holiday home rental outside of Leonardtown is located on the beach, and has a balcony, a garden and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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, 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.