A rural landscape with a barn, trees, and a fence under a sunset sky.

Leonardtown Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Leonardtown holiday rentals

Coffee/tea maker, fridge, microwave, oven

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is HK$1,842
HK$4,389 total
includes taxes & fees
20 Jul - 21 Jul
Anne & Fred`s Leonardtown Home W/ Arcade room!
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$1,682
HK$2,555 total
includes taxes & fees
20 Jul - 21 Jul
Coles Point Marina
Smart TV, books

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$3,136
HK$6,331 total
includes taxes & fees
21 Jul - 22 Jul
4-BR Waterfront Turret Home
Interior

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
10.0 out of 10, Exceptional, (1 review)
"We were going to an evening event at Stratford Hall (about 25 min away). There is so much history in the area. Beautiful spot on the river. The screened in porch was the bomb! Huge. So relaxing. Well stocked. Easy check out. Do pay attention to room configuration. The bedroom with twins was a loft like area but had the nicer bathroom. We used the kayaks. Had everything we needed. Host communication was great despite Vrbo platform was a challenge."
United States
Paige
The price is HK$2,626
HK$4,572 total
includes taxes & fees
18 Aug - 19 Aug
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is HK$1,223
HK$2,510 total
includes taxes & fees
21 Jul - 22 Jul
Soul Oasis - home on the Chesapeake Bay
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.4 out of 10, Exceptional, (11 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 HK$1,200
HK$2,086 total
includes taxes & fees
20 Jul - 21 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is HK$2,705
HK$3,318 total
includes taxes & fees
20 Jul - 21 Jul
2 Bedroom Cottage at Coles Point Marina
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is HK$2,689
HK$6,257 total
includes taxes & fees
2 Aug - 3 Aug
Charming Waterfront 3-bedroom house in Piney Point
Interior

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is HK$3,395
HK$8,963 total
includes taxes & fees
20 Jul - 21 Jul
Lakefront Cabin Near Solomons Island w/ Hot Tub
Interior

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is HK$4,006
HK$8,971 total
includes taxes & fees
20 Jul - 21 Jul
Lakefront Cabin Near Solomons Island w/ Hot Tub
Property grounds

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is HK$3,622
HK$6,715 total
includes taxes & fees
22 Jul - 23 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Outdoor dining

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (38 reviews)
"The host went above and beyond to make us feel welcome. From the smooth check-in to the thoughtful welcome basket, every detail was handled with care. We especially loved the riverfront home and all the commodities included. A true home away from home!"
United States
Evelyn C.
The price is HK$3,410
HK$5,996 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront Reset: Views, Games, Boats & Total Calm
Interior

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (11 reviews)
"We had a wonderful stay! Beautiful waterfront home with a brand new pier overlooking the river and a perfect sunset. Quiet location, perfectly appointed and great location next to parks, St Mary’s City and campus. Highly recommend!"
United States
Kurt O.
The price is HK$1,372
HK$3,017 total
includes taxes & fees
20 Jul - 21 Jul
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is HK$1,623
HK$2,734 total
includes taxes & fees
20 Jul - 21 Jul
Bright and airy waterfront getaway
Exterior

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (67 reviews)
"Always a great stay! "
United States
Amy H.
The price is HK$1,037
HK$2,246 total
includes taxes & fees
26 Jul - 27 Jul
Rest & Recharge, A-frame Cabin on Winery Grounds
TV, fireplace, video games, books

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is HK$3,795
HK$7,828 total
includes taxes & fees
12 Aug - 13 Aug
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Coffee/tea maker, fridge, microwave, oven

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (16 reviews)
"Everything about this stay was FANTASTIC. The host was amazing, the condo was in excellent condition and the view is AMAZING! Enjoyed everything about this stay!"
United States
N C.
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Exterior

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is HK$1,960
HK$4,231 total
includes taxes & fees
23 Jul - 24 Jul
River Refresh - Waterfront with Spa on Placid Bay
Dining

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (17 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is HK$1,665
HK$3,318 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
TV, fireplace

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (2 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$826
HK$1,881 total
includes taxes & fees
22 Jul - 23 Jul
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
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

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

10/10 Excellent
"The room was clean, the breakfast was very good and the staff were helpful. Look."
Martha 2-night trip
Posted 2 hours ago
Springhill Suites by Marriott Prince Frederick

Find out more about Leonardtown

Search for holiday rentals in Leonardtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Leonardtown using one of the methods below:

  • View our selection of featured holiday rentals in Leonardtown
  • Use the map to find apartments and other holiday homes in the Leonardtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Leonardtown while they last

Look no further and take a look at our great range of rental properties in Leonardtown!

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?

Private Chesapeake Bay Beach community…love to feel the sand between your toes?: This holiday home rental outside of Leonardtown is located on the waterfront, and has a patio, a garden 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 an oven, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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, Leonardtown Town Hall and Saint Mary's Fairground 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.