Leonardtown Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • 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

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

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (58)
"Beautiful location "
United States
Jonathan M.
2 Acre Oasis with Private Beach! Family and dog friendly!

Cheery, Peaceful Water Front Cabin on Winery Grounds

Cheery, Peaceful Water Front Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (56)
"Very quiet and great location."
United States
Cindy B.
The price is NZ$324
includes taxes & fees
14 Dec - 15 Dec
Cheery, Peaceful Water Front Cabin on Winery Grounds

Relaxation awaits! Potomac River Waterfront Home.

Relaxation awaits! Potomac River Waterfront Home.
Lottsburg
10.0 out of 10, Exceptional, (144)
"We really enjoyed our stay at this great property."
United States
Joe F.
Relaxation awaits! Potomac River Waterfront Home.

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

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Drayden
9.8 out of 10, Exceptional, (78)
"My family and I had a wonderful time. This is a great place to get away from it all. We loved fishing from the dock and having a fire by the water at night. Thanks again for a great time."
United States
Jeramie E.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

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

Tiny, Funky, and Full of Love - Welcome to the Love Shack
Piney Point
10.0 out of 10, Exceptional, (14)
"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

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
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 NZ$483
includes taxes & fees
16 Dec - 17 Dec
Soul Oasis - home on the Chesapeake Bay

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

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.

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

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

Luxurious 3 Bedroom Riverfront Condo with Private Deck

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

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

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Port Republic
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand
Point Lookout
10.0 out of 10, Exceptional, (125)
"Beautiful home in a stunning location! The house is comfortable and has all the amenities needed for a relaxing retreat. The backyard and beach are really incredible - Hays Beach is my new favorite stretch along the Chesapeake Bay. We plan to return for another family vacation!"
United States
Courtney F.
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

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

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Newburg
9.8 out of 10, Exceptional, (155)
"Lovely place and location!"
United States
Christa W.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
Church Creek
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

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

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Port Republic
10.0 out of 10, Exceptional, (124)
"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

Xmas Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr

Xmas Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr
Montross
10.0 out of 10, Exceptional, (30)
"Great spot"
United States
SHAWN W.
The price is NZ$791
includes taxes & fees
15 Dec - 16 Dec
Xmas Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Lottsburg
10.0 out of 10, Exceptional, (63)
"We had a wonderful stay for Labor Day weekend. So much is provided by the owners, paddle boards, kayak, water mats, everything you need to enjoy the water. The house is beautifully decorated, clean and well stocked. Don't miss the sunrises. Hope to be back."
United States
Robin M.
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Colonial Beach Cottage, 7 minutes walk to beach!

Colonial Beach Cottage, 7 minutes walk to beach!
Colonial Beach
9.2 out of 10, Wonderful, (35)
"Easy check in, over all nice place with a very convenient location. Property owner VERY responsive and excellent. We had a great 3 night 4 day stay."
United States
Kye H.
Colonial Beach Cottage, 7 minutes walk to beach!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Hague
9.8 out of 10, Exceptional, (28)
"Great stay, easy check-in/check-out, highly recommend"
United States
kevin l.
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Beach & River Retreat. Spectacular house with private sand beach and hot tub!

Beach & River Retreat. Spectacular house with private sand beach and hot tub!
Montross
10.0 out of 10, Exceptional, (51)
"Spacious with great kitchen to cook for manyEasy kayak and SUP access and great water views"
United States
debra s.
Beach & River Retreat. Spectacular house with private sand beach and hot tub!

Stunning Water Front Home with Private Dock and Beach and Sunsets

Stunning Water Front Home with Private Dock and Beach and Sunsets
Lusby
10.0 out of 10, Exceptional, (27)
"Great place. Would definitely stay here again. "
United States
Joshua M.
Stunning Water Front Home with Private Dock and Beach and Sunsets
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.
Save an average of 15% on thousands of hotels when you're signed in

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 NZ$324 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?

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.