Leonardtown, MD Vacation Homes from AED 995

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Our top choices for Leonardtown vacation homes

A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

1. 2 Acre Oasis with Private Beach! Family and dog friendly!

Leonardtown

Carol L.

AED 3,109 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a bed, a bench, a nightstand, a ceiling fan, and large windows.

2. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

Montross

Julie P.

AED 1,756 total

includes taxes & fees

26 Oct - 27 Oct

A spacious living room with a large sofa, a television, and a view of the ocean.

3. 4-BR Waterfront Turret Home

Solomons

Thomas S.

AED 2,697 total

includes taxes & fees

18 Oct - 19 Oct

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

4. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

AED 995 total

includes taxes & fees

26 Oct - 27 Oct

A covered patio with a view of a lake, furnished with chairs and a table.

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

Lexington Park

Andrea B.

AED 1,501 total

includes taxes & fees

20 Oct - 21 Oct

A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

6. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

Colonial Beach

Crystal W.

AED 1,217 total

includes taxes & fees

28 Oct - 29 Oct

An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

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

Montross

Nicole P.

AED 1,770 total

includes taxes & fees

28 Oct - 29 Oct

A two-story house with a balcony, surrounded by trees and a wooden fence.

8. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

AED 2,743 total

includes taxes & fees

30 Oct - 31 Oct

A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

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

Lusby

Nicholas L.

AED 3,136 total

includes taxes & fees

20 Oct - 21 Oct

A pathway lined with trees and lights leading to a wooden building with a visible window.

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

Lusby

Anonymous traveler

AED 3,146 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

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

Montross

N C.

AED 1,974 total

includes taxes & fees

18 Oct - 19 Oct

A lakeside view with chairs and a table, a rainbow, and trees.

12. Bright and airy waterfront getaway

Benedict

George

AED 1,304 total

includes taxes & fees

18 Oct - 19 Oct

A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

13. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lusby

Tanya S.

AED 4,279 total

includes taxes & fees

26 Oct - 27 Oct

A deck with outdoor furniture overlooking a lake.

14. River Refresh - Waterfront with Spa on Placid Bay

Colonial Beach

Kelly P.

AED 1,962 total

includes taxes & fees

18 Oct - 19 Oct

A small, single-story house with a red door, a porch with white railings, and a brick pathway leading to the entrance.

15. Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

King George

"The host was great. The house was wonderful. There were 3 bedrooms and we each had a bedroom to ourselves. The screened in porch was amazing . I had my coffee out in the screen porch each morning while I was able to watch TV. The kitchen was beautiful and had stainless steel appliances. Kitchen had everything we needed. The only down fall was the pool. We could not use the top step due to a crack so pool time was very limited. At night the grounds are well lit. Bathroom was well stocked. I did...

Anonymous traveler

AED 1,037 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a central island, bar stools, pendant lights, and a wooden cabinet.

16. The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly

Colonial Beach

Jennifer B.

AED 4,185 total

includes taxes & fees

2 Nov - 3 Nov

A covered outdoor deck with wicker furniture, a glass door leading inside, and a view of a lake surrounded by trees.

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

Heathsville

Liudmila U.

AED 2,290 total

includes taxes & fees

18 Oct - 19 Oct

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Top Leonardtown Hotel Reviews

Sleep Inn & Suites California MD

10/10 Excellent

"We stayed a couple of nights for a friend’s wedding and the location and the staff were perfect for us!! Thank you so Much."

Hilton Garden Inn Solomons

8/10 Good

"The room was clean and away from the elevators with no issues for the specific room. The only reason this is not a 5 star review is that there is no accommodation for customers / guests that need a nightstand on both sides of the bed. In our situation both customers have a CPAP machine. The reservation was for 2 guests and the room was a queen bed and upon arrival we had to decide who was going to sleep without their CPAP machine because the room has no bedside table or electrical outlets on the outer edge of the bed. Regardless of the medical need when will Hotels learn that both sides of the bed need a place to hold their CPAP or book or tea."

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

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Check prices for these dates

Our top choices for Leonardtown vacation homes

1. 2 Acre Oasis with Private Beach! Family and dog friendly!