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Leonardtown Holiday Rentals

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Holiday Rentals in Leonardtown

Anne & Fred`s Leonardtown Home W/ Arcade room!
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."
The price is AU$833
includes taxes & fees
19 Oct - 20 Oct
Anne & Fred`s Leonardtown Home W/ Arcade room!
Cheery, Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (53)
"Great spot for a family of 4. Very quiet and clean."
The price is AU$312
includes taxes & fees
27 Oct - 28 Oct
Cheery, Peaceful Water Front Cabin on Winery Grounds
Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (35)
"Lovely house with tons of character. Clean and comfortable. A few steps from water. "
The price is AU$484
includes taxes & fees
20 Oct - 21 Oct
Soul Oasis - home on the Chesapeake Bay
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.6 out of 10, Exceptional, (7)
"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."
The price is AU$571
includes taxes & fees
20 Oct - 21 Oct
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Riverside Dreams -golfcart-views-screened porch-
2.0 star property
10.0 out of 10, Exceptional, (3)
"We found the view and the accommodations quite lovely."
The price is AU$596
includes taxes & fees
19 Oct - 20 Oct
Riverside Dreams -golfcart-views-screened porch-
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
9.4 out of 10, Exceptional, (6)
"Great place to stay"
The price is AU$274
includes taxes & fees
21 Oct - 22 Oct
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AU$468
includes taxes & fees
19 Oct - 20 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Sail Away
10.0 out of 10, Exceptional, (7)
"Very clean and well kept. Pictures were accurate. I would stay here again. "
The price is AU$420
includes taxes & fees
19 Oct - 20 Oct
Sail Away
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (13)
"Very clean, awesome location and amazing hosts!! "
The price is AU$407
includes taxes & fees
20 Oct - 21 Oct
Waterfront Solomons Apartment
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
10.0 out of 10, Exceptional, (3)
"Everything was very clean and well put together. Loved the view!"
The price is AU$585
includes taxes & fees
20 Oct - 21 Oct
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
2.0 star property
9.4 out of 10, Exceptional, (9)
"This house is great and has everything we needed. It was very clean and within walking distance of the beach and restaurants. Loved it and would book again!"
The price is AU$505
includes taxes & fees
19 Oct - 20 Oct
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"The accommodations were superb and being on the water was amazing!"
The price is AU$548
includes taxes & fees
1 Nov - 2 Nov
Cottage Located on the Patuxent River!
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks
3.0 star property
The price is AU$1,115
includes taxes & fees
19 Oct - 20 Oct
Lakefront Log Cabin Retreat 3br-2ba Hot Tub+kayaks
Waterfront home where you can relax or enjoy the things the Northern Neck.
9.8 out of 10, Exceptional, (10)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
The price is AU$470
includes taxes & fees
23 Oct - 24 Oct
Waterfront home where you can relax or enjoy the things the Northern Neck.
Fall Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr
10.0 out of 10, Exceptional, (29)
"Great spot"
The price is AU$686
includes taxes & fees
28 Oct - 29 Oct
Fall Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
10.0 out of 10, Exceptional, (7)
"Clean and easy "
The price is AU$574
includes taxes & fees
26 Oct - 27 Oct
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (4)
"They thought of everything. I would definitely come back for another stay."
The price is AU$682
includes taxes & fees
21 Oct - 22 Oct
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14)
"My wife, daughter and I really enjoyed the serene and privacy of the property. The view of the lake and outdoors was beautiful. The home was clean and cozy and we plan to return. "
The price is AU$775
includes taxes & fees
11 Nov - 12 Nov
Luxury Modern Waterfront Retreat
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.4 out of 10, Exceptional, (3)
"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. "
The price is AU$638
includes taxes & fees
3 Nov - 4 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
River Refresh - Waterfront with Spa on Placid Bay
10.0 out of 10, Exceptional, (18)
"Extremely clean Cottqge overlook the water. We arrived just in time to see the incredible sunset!!!! "
The price is AU$816
includes taxes & fees
26 Oct - 27 Oct
River Refresh - Waterfront with Spa on Placid Bay
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$312 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?

Waterfront with spectacular view, close to restaurants and bars: This holiday home rental outside of Leonardtown is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 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, Port of Leonardtown Winery 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.