Madison Vacation Rentals

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Vacation Rentals in Madison

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD

$327 nightly

$347 total

Feb 2 - Feb 3

Total with taxes and fees

A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD

Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD

Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and 3 minutes by foot from Muskrat Park.

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick MD

$385 nightly

$408 total

Jan 25 - Jan 26

Total with taxes and fees

With a stay at this vacation home in Prince Frederick, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.

Shewell's A-Frame on Mill Creek

Lusby MD

Located in Lusby, this vacation home is within a 5-minute drive of Drum Point Lake and Chesapeake Bay.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic MD

When you a stay at this vacation home in Port Republic, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Discover tranquility near Calvert Cliffs

Saint Leonard MD

Located in St. Leonard, this vacation home is on the waterfront, within a 10-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and Museum.

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Lusby MD

Located in Lusby, this vacation home is a 5-minute drive from Chesapeake Bay and 6 minutes from Chesapeake Hills Golf Course.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick MD

Located in Prince Frederick, this vacation home is near the beach, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Easton MD

With a stay at this vacation home in Easton, you'll be on the beach, and 6.6 mi (10.7 km) from Saint Michaels Village and 7.3 mi (11.7 km) from St. Michaels Winery.

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford MD

A stay at this vacation home places you in the heart of Woolford, and within a 15-minute drive of Blackwater National Wildlife Refuge.

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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.