Madison Vacation Rentals

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Vacation Rentals in Madison

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons MD

A stay at this vacation home places you in the heart of Solomons, within a 5-minute walk of J.C. Lore Oyster House and Solomons Yachting Center.

Kitchen

Washer

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD

$324 nightly

$343 total

Jan 5 - Jan 6, 2026

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.

Kitchen

Washer

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.

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Kitchen

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.

Kitchen

Washer

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

St. Michaels MD

With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.

Kitchen

Washer

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

Prince Frederick MD

$372 nightly

$394 total

Dec 8 - Dec 9

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.

Kitchen

Washer

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.

Kitchen

Washer

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.

Kitchen

Washer

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.

Kitchen

Washer

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.

Kitchen

Washer

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

Prince Frederick MD

$344 nightly

$365 total

Dec 17 - Dec 18

Total with taxes and fees

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

Kitchen

Washer

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

Tilghman Island MD

With a stay at this vacation home in Tilghman, you'll be within a 5-minute walk of Talbot County Library Tilghman Branch and Tilghman Watermen’s Museum.

Kitchen

Washer

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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.