
Leonardtown Vacation Rentals
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Our top choices for Leonardtown vacation rentals

1. Anne & Fred`s Leonardtown Home W/ Arcade room!
Anne & Fred`s Leonardtown Home W/ Arcade room!
2. 2 Acre Oasis with Private Beach! Family and dog friendly!
2 Acre Oasis with Private Beach! Family and dog friendly!
3. Coles Point Marina
Coles Point Marina
4. 4-BR Waterfront Turret Home
4-BR Waterfront Turret Home
5. 2 Bedroom Cottage at Coles Point Marina
2 Bedroom Cottage at Coles Point Marina
6. Cozy Virginia Potomac Riverfront Cottage
Cozy Virginia Potomac Riverfront Cottage
7. Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
8. Charming Waterfront 3-bedroom house in Piney Point
Charming Waterfront 3-bedroom house in Piney Point
9. Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake Bay
10. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
11. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
12. 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.
13. Waterfront Reset: Views, Games, Boats & Total Calm
Waterfront Reset: Views, Games, Boats & Total Calm
14. Rest & Recharge, A-frame Cabin on Winery Grounds
Rest & Recharge, A-frame Cabin on Winery Grounds
15. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
16. Lakefront Cabin Near Solomons Island w/ Hot Tub
Lakefront Cabin Near Solomons Island w/ Hot Tub
17. Lakefront Cabin Near Solomons Island w/ Hot Tub
Lakefront Cabin Near Solomons Island w/ Hot Tub
18. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
19. Bright and airy waterfront getaway
Bright and airy waterfront getaway
20. Sail Away To
Sail Away ToFind vacation rentals that suit your style
Top Leonardtown Hotel Reviews

River Edge Inn
Find out more about Leonardtown
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Leonardtown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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