Holiday Rentals Leonardtown from £183: Find Short-Term Rentals & Holiday Accommodations

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Leonardtown holiday rentals

A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

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

Leonardtown

Christy C.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

2. 2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown

Carol L.

includes taxes & fees

1 Dec - 2 Dec

A single-story house with a front porch, a small deck, and a number '4' on the side.

3. Coles Point Marina

Hague

John

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a bed, a ceiling fan, two windows with curtains, a bedside lamp, a potted plant, and a door.

4. 8BD Retreat | Hot Tub, Movie Room, Gym & Pool

California

includes taxes & fees

17 Nov - 18 Nov

A marina with boats docked, calm water, and a sunset sky.

5. 1BR Solomons Island Home with Private Deck

Solomons

includes taxes & fees

13 Dec - 14 Dec

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

6. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

includes taxes & fees

1 Dec - 2 Dec

A wooden cabin with a balcony, surrounded by lush greenery and trees.

7. Rest & Recharge, A-frame Cabin on Winery Grounds

Colonial Beach

Amy H.

includes taxes & fees

30 Nov - 1 Dec

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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

Benedict

ed r.

includes taxes & fees

16 Nov - 17 Nov

A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

9. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

Colonial Beach

Crystal W.

includes taxes & fees

19 Nov - 20 Nov

A spacious living room with a large sofa, a television, and a view of the ocean.

10. 4-BR Waterfront Turret Home

Solomons

Thomas S.

includes taxes & fees

17 Nov - 18 Nov

A room with a large window overlooking a beach with a wooden pier and lounge chairs.

11. Cozy Virginia Potomac Riverfront Cottage

Hague

Sharon D.

includes taxes & fees

16 Nov - 17 Nov

A coastal area with a sandy beach, a clear blue sea, and a small settlement with houses.

12. Waterfront Retreat w/Private Hot Tub · Game Room · Fire Pit · Kayaks

Montross

Julie P.

includes taxes & fees

16 Nov - 17 Nov

A covered patio with a view of a lake, furnished with chairs and a table.

13. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Lexington Park

Andrea B.

includes taxes & fees

16 Nov - 17 Nov

A waterfront hotel with a dock extending into the water, a large building with multiple floors, and a clear sky.

14. Sail Away To

Colonial Beach

Tina S.

includes taxes & fees

16 Nov - 17 Nov

A room with a wooden floor, a gray sofa, a blue armchair, and a table.

15. Lusby 3BD Family Beach House - Steps to the Sand!

Lusby

includes taxes & fees

16 Nov - 17 Nov

A backyard with a wooden bench, two white cushioned chairs, a table, and a tree providing shade.

16. Solomons Spacious 6-BD Family Home with Hot Tub

Solomons

includes taxes & fees

18 Nov - 19 Nov

A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

17. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Lusby

Dani B.

includes taxes & fees

17 Nov - 18 Nov

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

18. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

includes taxes & fees

16 Nov - 17 Nov

An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

19. Waterfront Reset: Views, Games, Boats & Total Calm

Montross

Nicole P.

includes taxes & fees

1 Dec - 2 Dec

A two-story house with a balcony, surrounded by trees and a wooden fence.

20. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

includes taxes & fees

16 Nov - 17 Nov

View all properties

Find holiday rentals that suit your style

Top Leonardtown Hotel Reviews

A hotel lobby with wooden doors, a reception desk, and a seating area with tables and chairs.

Comfort Inn & Suites Lexington Park near Pax River

Lexington Park

10/10 Excellent

Paul

A hotel lobby with a dining area, seating, a fireplace, and a view of the outside through large windows.

Hampton Inn by Hilton Lexington Park

Lexington Park

10/10 Excellent

Edwin

A wooden chair on a balcony overlooking a sunset over a body of water.

Island Inn & Suites, an Ascend Collection Hotel

Piney Point

8/10 Good

richard

A modern hotel lobby with seating areas, a reception desk, and a staircase.

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

California

10/10 Excellent

Darren

A modern kitchen area with a checkered floor, a central island, and a bright red door.

Hampton Inn Dahlgren

King George

10/10 Excellent

James

A Holiday Inn Express hotel with a modern facade, a prominent sign, and a well-lit entrance.

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

8/10 Good

We were visiting Chesapeake Beach & Bay in Maryland & opted to stay here. The reception staff were lovely; do take their recommendation of visiting Jerry's for dinner - the food is amazing! Breakfast was pretty good, once we'd convinced the breakfast staff to re-stock everything. The pool was a little disappointing. There were towels strewn everywhere & no fresh ones when I went to use the pool. That having been said they did deal with the issue promptly when I raised it. The water for the pool...

RiaG

A beachside view with a wooden deck, tables, and chairs, overlooking a sandy beach and calm sea.

Colonial Beach Plaza Bed & Breakfast

Colonial Beach

10/10 Excellent

Eloïse

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 £183 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 St. Mary's County Arts Council, 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?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This holiday home rental outside of Leonardtown offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Leonardtown?

With 9 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 Indian Village Archeological Park are a couple of scenic spots to enjoy the outdoors, whereas North End Gallery is one of the cultural attractions. While here, Breton Bay Golf Course 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.

Search Holiday Rentals in Leonardtown

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Leonardtown holiday rentals

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

2. 2 Acre Oasis with Private Beach! Family and dog friendly!

3. Coles Point Marina

4. 8BD Retreat | Hot Tub, Movie Room, Gym & Pool

5. 1BR Solomons Island Home with Private Deck

6. Soul Oasis - home on the Chesapeake Bay

7. Rest & Recharge, A-frame Cabin on Winery Grounds

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

9. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

10. 4-BR Waterfront Turret Home

11. Cozy Virginia Potomac Riverfront Cottage

12. Waterfront Retreat w/Private Hot Tub · Game Room · Fire Pit · Kayaks

13. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

14. Sail Away To

15. Lusby 3BD Family Beach House - Steps to the Sand!

16. Solomons Spacious 6-BD Family Home with Hot Tub

17. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

18. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

19. Waterfront Reset: Views, Games, Boats & Total Calm

20. Charming Waterfront 3-bedroom house in Piney Point

Find holiday rentals that suit your style

Top Leonardtown Hotel Reviews

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent

Find out more about Leonardtown

Leonardtown holiday rentals: An excellent choice for every season

How to find incredible deals on Leonardtown rentals

Frequently Asked Questions

Are there holiday rentals in Leonardtown?

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

How many holiday rentals will I find in Leonardtown?

What’s there to see and do in Leonardtown?

What’s a holiday rental in Leonardtown like?