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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
15 Apr - 16 Apr
Tomorrow
16 Apr - 17 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

Holiday Rentals in Leonardtown

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Outdoor spa tub

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

10.0 out of 10, Exceptional, (32)
"The place had was great, hot tub overlooking private beach on the Potomac. Kitchen had nearly everything you could need. Very responsive host. There is spotty cell service at the house, but the WiFi helps. If I was going to add anything to this rental, it would definitely be a full-length mirror. "
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Fridge, microwave, oven, stovetop

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (30)
"My husband and i live up the road but we rented this house for his parents, for the weekend. The location is absolutely fantastic and the house is gorgeous. I could have sat on the back deck for hours. Dan was very responsive to all of my questions. I wouldn't hesitate to rent from him, again. "
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

10.0 out of 10, Exceptional, (21)
"."
The price is HK$853
HK$2,022 total
includes taxes & fees
23 Apr - 24 Apr
Soul Oasis - home on the Chesapeake Bay
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

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

9.8 out of 10, Exceptional, (128)
"Great little weekend getaway very quiet and enjoyed the relaxation . Very cute and clean cottage on the water "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (160)
"The house was awesome, the view couldn’t have been better. Loved everything about it, quiet and peaceful and it is on a dead end short road with wildlife in the yard in the morning, deer, fox, blue heron, bald eagle, geese and ducks, just fabulous. Will definitely be going back soon I hope."
Waterfront Wildlife Retreat on the Patuxent River
Waterfront House with Dock, Kayaks, & Sailboat!
TV, fireplace, ping pong, books

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!
Cheery, Peaceful Water Front Cabin on Winery Grounds
TV, fireplace, DVD player, books

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (41)
"It felt like home, it was a wonderful place!"
The price is HK$1,055
HK$2,194 total
includes taxes & fees
22 Apr - 23 Apr
Cheery, Peaceful Water Front Cabin on Winery Grounds
Private Beach Front Getaway at The Sunshine Beach Cottage.
Property grounds

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (64)
"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.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Terrace/patio

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

9.8 out of 10, Exceptional, (59)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront with spectacular view, close to restaurants and bars
Exterior

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (31)
"Everything was great. "
Waterfront with spectacular view, close to restaurants and bars
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (67)
"Extraordinary. Love it . "
Waterfront Cottage in Beautiful Hoopers Island
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Terrace/patio

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

10.0 out of 10, Exceptional, (174)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

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

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay
Fridge, microwave, oven, stovetop

Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay

9.8 out of 10, Exceptional, (46)
"Our family was gathering in Heathsville for Christmas and additional accommodations were needed to ensure everyone’s comfort over the holiday. While much of our time was spent at ‘Grandma’s house’ a few miles away, this was the perfect place for us to enjoy late evenings and early mornings. Cousins could be heard laughing long into the night as they caught up in the ‘loft room’, each morning started with a stroll in the dock, and days ended by gazing at the stars.Despite a slight communication...
Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Terrace/patio

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

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!
Screened Patio, Deck & Grill: Saint Inigoes Home!
Fridge, microwave, stovetop, dishwasher

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.0 out of 10, Wonderful, (2)
"Sweet little place on the water. Quiet neighborhood. Quick trip to campus."
Screened Patio, Deck & Grill: Saint Inigoes Home!
Waterfront Relaxing Getaway
Fridge, microwave, oven, stovetop

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
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

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

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

10.0 out of 10, Exceptional, (43)
"The property was fantastic, as described. Crabbing was good. Frank was very responsive at all times. We had an issue with the hot water. Frank and 2 of his workers were there the next day to fix it. We did not encounter any jellyfish where we swam in front of the house. Our only issue was the location is not ideal for doing other things as there’s just not a lot to do unless you drive an hour away. Our teenagers made the hour one-way trip a few times to go elsewhere. Overall, we had an awesome...
Beach & River Retreat. Spectacular house with private sand beach and hot tub!
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
Sign in
Sign up, it's free

Other types of properties in Leonardtown you may be interested in

The Inn at Leonardtown, Ascend Hotel Collection
Lobby

The Inn at Leonardtown, Ascend Hotel Collection

2.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful renovations have resulted in an updated, clean hotel. The staff is friendly and m, although we stayed for just one night, we would definitely return!"
The price is HK$1,022
HK$1,134 total
includes taxes & fees
11 May - 12 May
The Inn at Leonardtown, Ascend Hotel Collection
River Edge Inn
Exterior

River Edge Inn

2.5 star property
8.2 out of 10, Very good, (273)
"It was fine. "
The price is HK$837
HK$961 total
includes taxes & fees
28 Apr - 29 Apr
River Edge Inn
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Premium bedding, desk, blackout curtains, iron/ironing board

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3.0 star property
7.6 out of 10, Good, (1007)
"BREAKFAST AREA WAS A LITTLE TOO SMALL "
The price is HK$718
HK$798 total
includes taxes & fees
20 Apr - 21 Apr
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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This holiday home rental outside of Leonardtown is located on a river, and has a fireplace, a balcony 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 can relax into your holiday with a garden and a selection of games.

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 Leonardtown Park 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.