Smith Island Cottages

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Cottages in Smith Island

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Reedville VA

With a stay at this cottage in Reedville, you'll be within a 5-minute drive of Chesapeake Bay and Fleeton Beach.

Kitchen

Pet friendly

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Smith Island MD

When you stay at this cottage in Smith Island, you'll be on the waterfront and steps from Terrapin Sand Point.

Kitchen

Washer

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis VA

With a stay at this cottage in Saxis, you'll be 13.8 mi (22.3 km) from Bloxom Winery and 16.3 mi (26.2 km) from Kegotank Bay.

Kitchen

Washer

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 1 Min Walk to Sand

Scotland MD

With a stay at this cottage in Scotland (Point Lookout), you'll be within a 15-minute drive of Chesapeake Bay and Confederate Memorial 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 within a 15-minute drive of Chesapeake Bay and Confederate Memorial Park.

Kitchen

Washer

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Scotland MD

With a stay at this cottage in Scotland (Point Lookout), you'll be within a 15-minute drive of Chesapeake Bay and Confederate Memorial Park.

Kitchen

Washer

Deal Island Bay Cottage

Deal Island MD

$248 nightly

$263 total

Dec 10 - Dec 11

Total with taxes and fees

When you stay at this cottage in Deal Island, you'll be near the beach, within a 5-minute drive of Shark Fin Shoal and Rock Island.

Kitchen

Washer

BEACH COTTAGE BY THE SEA....

Reedville VA

With a stay at this cottage in Reedville, you'll be on the beach, just steps from Chesapeake Bay and a 3-minute drive from Fleeton Beach.

Kitchen

Washer

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Scotland MD

$294 nightly

$325 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

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

Hays Beach House - Hot Tub - Private Beach

Scotland MD

With a stay at this cottage in Scotland (Point Lookout), you'll be within a 15-minute drive of Chesapeake Bay and Confederate Memorial Park.

Hot Tub

Kitchen

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Heathsville VA

Located in Heathsville, this cottage is on the waterfront, within a 10-minute drive of Cordreys Beach and Marshalls Beach.

Kitchen

Washer

Walk to Main Street: Family-friendly Crisfield Gem

Crisfield MD

Located in Crisfield, this cottage is within a 5-minute drive of Gov. Tawes Library and Crisfield Municipal Park.

Kitchen

Parking included

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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.