Leonardtown Vacation Rentals

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Vacation Rentals in Leonardtown

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek MD

With a stay at this vacation home in Fishing Creek, you'll be on the waterfront, within a 10-minute drive of Chesapeake Bay and P. L. Jones Marina.

Kitchen

Washer

Duck's Landing- A perfect 3-bedroom house with AC in charming Colonial Beach.

Colonial Beach VA

Located in Colonial Beach, this vacation home is within a 5-minute drive of Colonial Beach Historical Society and James Monroe Birthplace.

Kitchen

Pet friendly

Single family home with screened porch.

Fishing Creek MD

With a stay at this vacation home in Fishing Creek, you'll be within a 15-minute walk of Chesapeake Bay and P. L. Jones Marina.

Kitchen

Washer

Bright and airy waterfront getaway

Benedict MD

$361 nightly

$383 total

Nov 1 - Nov 2

Total with taxes and fees

Located in Benedict, this vacation home is on the waterfront, a 1-minute drive from Patuxent River and 7 minutes from Running Hare Vineyard.

Kitchen

Free WiFi

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

Montross VA

$479 nightly

$521 total

Oct 25 - Oct 26

Total with taxes and fees

Located in Montross, this vacation home is on the waterfront, within a 15-minute drive of Armstead T. Johnson High School and Montross Town Hall.

Kitchen

Washer

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach VA

When you stay at this vacation home in Colonial Beach, you'll be on the waterfront, within a 5-minute drive of James Monroe Birthplace and Colonial Beach.

Pool

Kitchen

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

Lexington Park MD

$406 nightly

$409 total

Oct 27 - Oct 28

Total with taxes and fees

With a stay at this vacation home in Lexington Park, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Historic St. Mary's City.

Kitchen

Washer

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

Leonardtown MD

$767 nightly

$847 total

Oct 26 - Oct 27

Total with taxes and fees

Located in Leonardtown, this vacation home is on the waterfront, within a 15-minute drive of Potomac River and Cecil's Old Mill.

Kitchen

Washer

Heron's Nest - Back Creek Villa Covered Deck

Solomons MD

With a stay at this vacation home in Solomons, you'll be within a 15-minute drive of Chesapeake Bay and J.C. Lore Oyster House.

Kitchen

Washer

Waterfront with spectacular view, close to restaurants and bars

Colonial Beach VA

When you stay at this vacation home in Colonial Beach, you'll be on the waterfront, within a 15-minute walk of Bayside Marina and Colonial Beach.

Kitchen

Washer

Welcome to Hickory House on the Chesapeake Bay!

Saint Leonard MD

When you stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Chesapeake Bay and 5 minutes by foot from Flag Harbor Marina.

Kitchen

Washer

River Haven — Firepit, Hot Tub, Views, Amenities Galore!

Montross VA

Located in Montross, this vacation home is on the waterfront, within a 15-minute drive of Trent Island and Hague Winery.

Hot Tub

Kitchen

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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.