Photo by Pla Jira

Leonardtown Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Leonardtown

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.

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

10.0 out of 10, Exceptional, (171)
"Great time!! Floridians playing in the snow!! Cozy fire afterwards in the fireplace. Picturesque drive up to the Navy Cabin, deer playing in the snow too."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

9.8 out of 10, Exceptional, (127)
"This was our mid-Winter get away from the city. The home is cute, quiet, and well appointed. The host is welcoming and responsive. We had a lovely, restful stay. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

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

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

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

10.0 out of 10, Exceptional, (39)
"We enjoyed a relaxing and rejuvenating time here while we rang in the new year. The home was lovely and the community was friendly."
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

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

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"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$451
includes taxes & fees
19 Feb - 20 Feb
Soul Oasis - home on the Chesapeake Bay

Beach Club: your own private "Caribbean" resort

9.8 out of 10, Exceptional, (9)
"Beautiful home with lots of room for all 11 of us to enjoy meals and hanging out. Great space to accommodate all ages from 4 to 80. Hosts were very responsive and made us feel welcome. The pavilion at the beach was awesome and we spent alot of time there. Great stay , great memories and all had a memorable time. "
Beach Club: your own private "Caribbean" resort

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

10.0 out of 10, Exceptional, (12)
"Myself, my partner, my 7 family members and our 2 pups stayed here for our annual vacation to Colonial Beach & our experience was nothing short of spectacular. The host is super fast at replying, made our check in process easy, and was super hospitable. They even accommodated our last minute wish to check in early! The ONLY thing I can think of that can be improved is the level of cleanliness. Everything was beautiful and clean except for areas underneath the rugs, which were covered with sand...
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (63)
"This was a great stay. Very nice, comfortable, great layout, convenient location. I highly recommend. "
Inviting and Serene Home on Monroe Bay Creek

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (39)
"I wanted a cozy retreat from DC over the holiday, and this was perfect. The dog loved running around the lot and taking walks around the vineyard. I loved the views of the pond, the eagles, and having plenty of space for puzzles, drawing, and reading. I took a speaker for tunes. No wifi but my cell worked fine, as did my hot spot. (Both are Verizon.) The king size bed is super comfortable, and I appreciated the nicer linens.Great location — 10 minutes from groceries, 15 minutes from downtown and...
The price is AU$456
includes taxes & fees
20 Feb - 21 Feb
Cheery, Peaceful Water Front Cabin on Winery Grounds

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!

El Camino

10.0 out of 10, Exceptional, (33)
"Very cute cabin. We enjoyed the peace and quiet. Ver close to our destin.ation, Point lookout."
El Camino

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is AU$935
includes taxes & fees
25 Feb - 26 Feb
4-BR Waterfront Turret Home

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (12)
"This was a great little cottage and was perfect for our stay. We wanted to be close to Valey Lee and the location was great. We will definitely consider staying again."
2 Bedroom Cozy Beach Cottage with Beach Access

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

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (66)
"the Hoopers Island area is amazingly wild and beautiful. we loved the Harriet Tubman visitors center just a short trip away, and the Blackwater Refuge just incredibly beautiful. the winter birds! we learned so much about the history and culture of the lower islands.the house is more cabin style, smaller than we anticipated, but we got used to that. it was full-on winter weather and wind, so we couldn't kayak as we'd hoped, and the coast was mostly rocks so hard to walk along. it's a place for...
Waterfront Cottage in Beautiful Hoopers Island

Sale! Game Theme~Pool+Fish+Boat+King bd+EV Charger

10.0 out of 10, Exceptional, (20)
"We came for R & R and we got it! Abbie was a great and responsive hostess and the house was perfect. Even though the weather was cold the views were still great, the layout was perfect and the furniture, especially the beds, was so comfortable. Getting groceries from the Food Lion was easy too. We're not big on water sports so unlikely we would come back in the summer, but maybe another visit in the spring or fall. Highly recommend!"
The price is AU$690
includes taxes & fees
19 Feb - 20 Feb
Sale! Game Theme~Pool+Fish+Boat+King bd+EV Charger
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.
Don't see what you're looking for?
See all available properties in Leonardtown
Save an average of 15% on thousands of hotels when you're signed in

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, (125)
"Nice small town inn with a couple of excellent dining options nearby. Check in was easy and very friendly. Room was clean, modern, with newer tv and heating units. Nice black out blinds instead of curtains. "
The price is AU$197
includes taxes & fees
16 Mar - 17 Mar
The Inn at Leonardtown, Ascend Hotel Collection

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1005)
"Great place to stay"
The price is AU$162
includes taxes & fees
2 Mar - 3 Mar
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Springhill Suites by Marriott Prince Frederick

3.0 star property
8.6 out of 10, Excellent, (855)
"Front desk was more than helpful and provided us a late check out. Pool and hot tub were clean. Breakfast was excellent. Staff and rooms were great! bed was comfy. "
The price is AU$250
includes taxes & fees
16 Mar - 17 Mar
Springhill Suites by Marriott Prince Frederick
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?

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! : This holiday home rental outside of Leonardtown is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease 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. It offers a patio, a garden and an arcade/games room so that you can immerse yourself in your holiday.

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 Leonard's Grant Recreation Area are a couple of lovely local spots to get outside and enjoy nature. While here, Leonardtown Town Hall and Port of Leonardtown Winery 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.