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

Leonardtown Vacation Rentals

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Check prices for these dates

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

Our top choices for Leonardtown vacation 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 AED 863
AED 2,005 total
includes taxes & fees
19 Jul - 20 Jul
Anne & Fred`s Leonardtown Home W/ Arcade room!
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AED 725
AED 1,128 total
includes taxes & fees
21 Jul - 22 Jul
Coles Point Marina
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 AED 403
AED 954 total
includes taxes & fees
23 Jul - 24 Jul
Rest & Recharge, A-frame Cabin on Winery Grounds
House (3 Bedrooms) | 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 AED 2,237
AED 4,603 total
includes taxes & fees
20 Jul - 21 Jul
Lakefront Cabin Near Solomons Island w/ Hot Tub
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 AED 1,341
AED 2,306 total
includes taxes & fees
11 Aug - 12 Aug
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
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 AED 918
AED 1,982 total
includes taxes & fees
23 Jul - 24 Jul
River Refresh - Waterfront with Spa on Placid Bay
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 AED 555
AED 1,156 total
includes taxes & fees
22 Jul - 23 Jul
Soul Oasis - home on the Chesapeake Bay
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AED 1,267
AED 1,555 total
includes taxes & fees
20 Jul - 21 Jul
2 Bedroom Cottage at Coles Point Marina
Smart TV, fireplace, table tennis, books

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (134 reviews)
"The property was very clean and well-stocked. Beds were comfortable and pictures matched reality. Jocelyn was so kind to leave us ingredients for smores and Easter eggs for my kids to have a hunt in the backyard. Overall, we had a wonderful stay and hope to make it back again some time!"
United States
Allie P.
The price is AED 1,157
AED 2,270 total
includes taxes & fees
19 Jul - 20 Jul
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
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 AED 845
AED 1,382 total
includes taxes & fees
20 Jul - 21 Jul
Bright and airy waterfront getaway
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 AED 780
AED 1,555 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Interior

Waterfront with spectacular view, close to restaurants and bars

Waterfront with spectacular view, close to restaurants and bars
Colonial Beach
9.8 out of 10, Exceptional, (73 reviews)
"We had a wonderful stay in this clean, beautiful waterfront property. The location was fantastic, and we loved watching the swan and osprey go about their days from the front porch. We were two couples (ages 45-75!), and the place and town were the perfect, relaxing getaway. "
United States
Alexis V.
The price is AED 397
AED 1,104 total
includes taxes & fees
17 Jul - 18 Jul
Waterfront with spectacular view, close to restaurants and bars
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 AED 1,260
AED 2,631 total
includes taxes & fees
19 Jul - 20 Jul
Charming Waterfront 3-bedroom house in Piney Point
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is AED 1,675
AED 3,355 total
includes taxes & fees
29 Jul - 30 Jul
'the Bayside Escape' Remote Chesapeake Bay Estate
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 AED 1,910
AED 4,678 total
includes taxes & fees
20 Jul - 21 Jul
Lakefront Cabin Near Solomons Island w/ Hot Tub
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
9.2 out of 10, Wonderful, (10 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 AED 624
AED 1,055 total
includes taxes & fees
20 Jul - 21 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
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, (10 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 AED 643
AED 1,413 total
includes taxes & fees
20 Jul - 21 Jul
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
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 AED 1,469
AED 2,966 total
includes taxes & fees
21 Jul - 22 Jul
4-BR Waterfront Turret Home
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 AED 1,697
AED 3,146 total
includes taxes & fees
22 Jul - 23 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Terrace/patio

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Heathsville
9.6 out of 10, Exceptional, (34 reviews)
"We loved the tranquility of the place, beautiful views, and the unique design of the house. The host was very responsive. It was a very relaxing stay. I am sure we will be coming back soon."
United States
Liudmila U.
The price is AED 1,010
AED 2,606 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
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

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"The staff were polite and kind. The rooms and amenities were clean. We will stay here again."
Tiffany 3-night trip
Posted 21 hours ago
avid hotel California - Lexington Park by IHG