Leonardtown Cottages

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Cottages in Leonardtown

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Lottsburg VA

With a stay at this cottage in Lottsburg, you'll be next to a golf course, and 9.7 mi (15.6 km) from Coan River Marina and 10.9 mi (17.6 km) from Heathsville Farmers' Market.

Kitchen

Washer

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Colonial Beach VA

Located in Colonial Beach, this cottage is on a river, within a 15-minute walk of Colonial Beach and Bayside Marina.

Kitchen

Washer

Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views

Heathsville VA

Located in Heathsville, this cottage is by the sea, within a 5-minute drive of Marshalls Beach and Cordreys Beach.

Kitchen

Washer

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek MD

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

Kitchen

Pet friendly

Soul Oasis - home on the Chesapeake Bay

Lusby MD

$305 nightly

$323 total

Sep 8 - Sep 9

Total with taxes and fees

With a stay at this cottage in Lusby, you'll be a 1-minute drive from Chesapeake Bay and 7 minutes from Cove Point Park.

Kitchen

Washer

Private Beach Front Getaway at The Sunshine Beach Cottage.

Scotland MD

With a stay at this cottage in Scotland (Point Lookout), you'll be a 1-minute drive from Chesapeake Bay and 10 minutes from Point Lookout State Park.

Kitchen

Washer

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict MD

$263 nightly

$290 total

Aug 24 - Aug 25

Total with taxes and fees

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

Free WiFi

Air conditioning

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Lottsburg VA

With a stay at this cottage in Lottsburg, you'll be on the beach, and 10.2 mi (16.4 km) from Coan River Marina and 11.4 mi (18.3 km) from Heathsville Farmers' Market.

Hot Tub

Kitchen

Sunrise Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek MD

When you stay at this cottage in Fishing Creek, you'll be on the waterfront, just steps from Chesapeake Bay and a 5-minute drive from P. L. Jones Marina.

Kitchen

Pet friendly

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

Scotland MD

With a stay at this cottage in Scotland (Point Lookout), you'll be steps from Chesapeake Bay and 14 minutes by foot from Confederate Memorial Park.

Kitchen

Washer

Sunnyside Up - Small Dog Friendly Waterfront Cottage

Colonial Beach VA

When you stay at this cottage in Colonial Beach, you'll be on the waterfront, within a 15-minute walk of Colonial Beach and Colonial Beach Historical Society.

Kitchen

Pet friendly

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Saint Leonard MD

When you stay at this cottage in St. Leonard, you'll be by the sea, within a 5-minute walk of Chesapeake Bay and Flag Ponds Nature Park.

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.