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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Leonardtown vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. 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 878
AED 2,164 total
includes taxes & fees
1 Sep - 2 Sep
Anne & Fred`s Leonardtown Home W/ Arcade room!
Exterior

2. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (58 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is AED 573
AED 1,184 total
includes taxes & fees
29 Sep - 30 Sep
Soul Oasis - home on the Chesapeake Bay
TV, fireplace

3. 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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AED 506
AED 1,038 total
includes taxes & fees
13 Sep - 14 Sep
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Sun loungers, beach towels

4. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is AED 611
AED 1,744 total
includes taxes & fees
8 Sep - 9 Sep
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Interior

5. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (54 reviews)
"My husband and I had a great 3 day getaway here. The view was spectacular! The convenience from walking to the dock to the house was awesome! The only “bad” thing I would say is the water….it has an awful sulfur smell that is very strong. Overall, we loved our stay & would stay here again!"
United States
Ashley D.
The price is AED 643
AED 1,259 total
includes taxes & fees
1 Sep - 2 Sep
Cozy Virginia Potomac Riverfront Cottage
Property grounds

6. 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, (15 reviews)
"The owner was very nice "
United States
karen
The price is AED 562
AED 962 total
includes taxes & fees
1 Sep - 2 Sep
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

7. Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (71 reviews)
"Always a great stay! "
United States
Amy H.
The price is AED 364
AED 883 total
includes taxes & fees
1 Sep - 2 Sep
Rest & Recharge, A-frame Cabin on Winery Grounds
Cottage, 2 Bedrooms, Kitchen | Exterior

8. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AED 709
AED 1,111 total
includes taxes & fees
3 Sep - 4 Sep
Coles Point Marina
Interior

9. 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, (15 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AED 643
AED 1,417 total
includes taxes & fees
9 Sep - 10 Sep
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Property grounds

10. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is AED 333
AED 1,258 total
includes taxes & fees
9 Sep - 10 Sep
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Property grounds

11. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 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 760
AED 1,324 total
includes taxes & fees
1 Sep - 2 Sep
Bright and airy waterfront getaway
Beach

12. Sail Away To

Sail Away To
Colonial Beach
9.6 out of 10, Exceptional, (17 reviews)
"The apartment was beautiful. he location made it easy to get around. Being able up front to the bay was awesome. Had my morning coffee on the deck."
United States
Christina
The price is AED 444
AED 1,083 total
includes taxes & fees
22 Sep - 23 Sep
Sail Away To
Interior

13. 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 900
AED 1,758 total
includes taxes & fees
15 Sep - 16 Sep
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Outdoor dining

14. Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
The price is AED 821
AED 1,845 total
includes taxes & fees
29 Sep - 30 Sep
Waterfront Reset: Views, Games, Boats & Total Calm
Exterior

15. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
Lusby
The price is AED 740
AED 1,564 total
includes taxes & fees
29 Sep - 30 Sep
3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
Smart TV, books

16. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AED 1,102
AED 2,582 total
includes taxes & fees
9 Sep - 10 Sep
4-BR Waterfront Turret Home
Exterior

17. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AED 1,267
AED 1,575 total
includes taxes & fees
1 Sep - 2 Sep
2 Bedroom Cottage at Coles Point Marina
Exterior

18. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 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 2,931 total
includes taxes & fees
1 Sep - 2 Sep
Charming Waterfront 3-bedroom house in Piney Point
Coffee/tea maker, fridge, microwave, oven

19. 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.
The price is AED 845
AED 2,078 total
includes taxes & fees
20 Sep - 21 Sep
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Dining

20. 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)
"Was very cozy and comfortable."
United States
sandi c.
The price is AED 834
AED 1,622 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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

8/10 Good
"It was a nice clean room and the breakfast was tasty."
Joseph 1-night trip
Posted 3 hours ago
Springhill Suites by Marriott Prince Frederick

Frequently asked questions

Are there vacation rentals in Leonardtown?

Yes, there are vacation rentals in Leonardtown near Saint Mary's Fairground, or you can choose a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Leonardtown has to offer?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This vacation home rental near Leonardtown is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Leonardtown?

With 9 Expedia vacation rentals, you're sure 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, Leonardtown Town Hall and Breton Bay Golf Course are other places worth a visit.

What’s a vacation rental in Leonardtown like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Leonardtown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.