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Leonardtown Holiday Rentals

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Holiday Rentals in Leonardtown

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

9.8 out of 10, Exceptional, (125)
"Lovely, quiet, clean and comfy "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (18)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is AU$469
includes taxes & fees
14 Jan - 15 Jan
Soul Oasis - home on the Chesapeake Bay

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (36)
"Such a cute rustic cabin with all the comforting details in all aspects! Nothing left out! Right next door to a winery a walk away… the perfect country fall getaway! We will definitely be back! It was a delightful location!"
The price is AU$476
includes taxes & fees
16 Jan - 17 Jan
Cheery, Peaceful Water Front Cabin on Winery Grounds

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (38)
"Heather and Ed are superb hosts. The home was very clean, well stocked and in the perfect location! "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

10.0 out of 10, Exceptional, (50)
"We had a chance to spend the weekend with our kids (age 18 and 20), and we couldn't have asked for a better location. The view was spectacular and the home was perfect. It was so peaceful and relaxing, yet there was so much to do—fishing, kayaking, paddleboarding, ping-pong, darts, board games, the list goes on. Everyone had a fantastic time. The only problem is that were only there for three nights!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

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

10.0 out of 10, Exceptional, (112)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (65)
"This is a small, sweet, comfortable cottage, and was just perfect for our brief getaway from the hurly-burly. The house is very well equipped, especially the kitchen, so cooking the local seafood was easy. The decor (loved the faux fireplace) was charming and welcoming, down to the live Poinsettia plant on the table when we got there. "
Waterfront Cottage in Beautiful Hoopers Island

The Schultz Estate

8.4 out of 10, Very good, (15)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (62)
"Absolutely lovely property. Everything is modern and clean. Beautiful nautical decor. On the water with lots of room and space. We loved it so much, we plan to use it again!!!"
Inviting and Serene Home on Monroe Bay Creek

Belle of the Chesapeake Bay

9.4 out of 10, Exceptional, (11)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach

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

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Maryland Vacation Rental w/ Private Pool & Dock

10.0 out of 10, Exceptional, (6)
"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "
Maryland Vacation Rental w/ Private Pool & Dock

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Waterfront Cottage w/ Private Beach + Deck!

9.8 out of 10, Exceptional, (15)
"Beautiful place and very peaceful stay!"
Waterfront Cottage w/ Private Beach + Deck!

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

El Camino

10.0 out of 10, Exceptional, (31)
"The place was phenomenal. Very clean. Very awesome to stay there. If you ever want to see the most beautiful sunset you have to go there. Plus the fishing was a lot of fun. Me and my husband really enjoyed the few days that we were there. Communication very good people. Very nice! That stayed next to us. I would definitely go back"
El Camino
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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Other types of properties in Leonardtown you may be interested in

The Inn at Leonardtown, Ascend Hotel Collection

2.5 star property
9.2 out of 10, Wonderful, (123)
"I liked the parking proximity and availability. "
The price is AU$198
includes taxes & fees
30 Jan - 31 Jan
The Inn at Leonardtown, Ascend Hotel Collection

Springhill Suites by Marriott Prince Frederick

3.0 star property
8.6 out of 10, Excellent, (849)
"Love the modern suite style with two closets, work area, the sink area by the refrigerator…definitely a plus. The staff had great customer service. Breakfast options were always a plus. Overall will definitely stay again when we visit that area."
The price is AU$195
includes taxes & fees
16 Jan - 17 Jan
Springhill Suites by Marriott Prince Frederick

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1002)
"the hotel staff was kind and attentive"
The price is AU$167
includes taxes & fees
16 Jan - 17 Jan
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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.

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 Relaxing Getaway: This holiday home rental outside of Leonardtown is located on a river, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Leonardtown?

With 12 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 Abell's Wharf are a couple of lovely local spots to get outside and enjoy nature. While here, Port of Leonardtown Winery 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.