Leonardtown Holiday Rentals

  • 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

9.4 out of 10, Exceptional, (6 reviews)
"It was very comfortable felt like home "
United States
Carol S.
The price is NZ$945
includes taxes & fees
22 Mar - 23 Mar
Anne & Fred`s Leonardtown Home W/ Arcade room!
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is NZ$707
includes taxes & fees
25 Mar - 26 Mar
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
9.8 out of 10, Exceptional, (59 reviews)
"Very private - very relaxing - accurate listing - great host"
United States
Patrick O.
The price is NZ$417
includes taxes & fees
23 Mar - 24 Mar
Rest & Recharge, A-frame Cabin on Winery Grounds
10.0 out of 10, Exceptional, (42 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is NZ$479
includes taxes & fees
24 Mar - 25 Mar
Soul Oasis - home on the Chesapeake Bay
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is NZ$448
includes taxes & fees
22 Mar - 23 Mar
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.2 out of 10, Wonderful, (10 reviews)
"We stayed for 2 nights in the fall for a family event at Stratford Harbor. The house was pristine and cozy. Loved the fenced backyard for the pets and the walk ability of the town. The host and back up host were VERY responsive."
United States
Saundra B.
The price is NZ$531
includes taxes & fees
22 Mar - 23 Mar
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

Holiday Home in Point Lookout

Kentigern Shed at Scotland Yards
9.6 out of 10, Exceptional, (155 reviews)
"Nice place to stay and very enjoyable environment. Management team is excellent to handle the property. "
United States
william s.
The price is NZ$538
includes taxes & fees
22 Mar - 23 Mar
Kentigern Shed at Scotland Yards

Apartment in Colonial Beach

Sail Away
9.8 out of 10, Exceptional, (9 reviews)
"Stay was wonderful!"
United States
Karen H.
The price is NZ$554
includes taxes & fees
14 Apr - 15 Apr
Sail Away
9.4 out of 10, Exceptional, (12 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is NZ$680
includes taxes & fees
25 Mar - 26 Mar
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is NZ$832
includes taxes & fees
14 Apr - 15 Apr
Dock+Kayaks+Firepit: Game Theme Waterfront Retreat
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is NZ$612
includes taxes & fees
23 Mar - 24 Mar
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Holiday Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is NZ$724
includes taxes & fees
23 Mar - 24 Mar
Luxury Modern Waterfront Retreat

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is NZ$530
includes taxes & fees
25 Mar - 26 Mar
Cottage Located on the Patuxent River!

Cabin in Hague

Coles Point Marina
2.0 star property
The price is NZ$638
includes taxes & fees
23 Mar - 24 Mar
Coles Point Marina
10.0 out of 10, Exceptional, (21 reviews)
"Fantastic amenities, beautiful view, cosy yet spacious!"
United States
Aaron M.
The price is NZ$901
includes taxes & fees
22 Mar - 23 Mar
River Refresh - Waterfront with Spa on Placid Bay
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is NZ$713
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (9 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is NZ$814
includes taxes & fees
23 Mar - 24 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
The price is NZ$499
includes taxes & fees
22 Mar - 23 Mar
2 Bedroom Cottage at Coles Point Marina

Holiday Home in Solomons

4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,292
includes taxes & fees
24 Mar - 25 Mar
4-BR Waterfront Turret Home
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$417 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?

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR: This holiday home rental outside of Leonardtown offers a fireplace, a patio and a BBQ 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. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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, 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.