Madison Vacation Rentals

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Vacation Rentals in Madison

Grace Cottage, Saint Michaels Walk to everything!

Saint Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and Saint Marys Square.

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD

When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.

Pool

Kitchen

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison MD

Located in Madison, this vacation home is on the waterfront, within a 15-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park.

Kitchen

Washer

Back Creek Villa Covered Deck

Solomons MD

With a stay at this vacation home in Solomons Island, you'll be just steps from Solomons Island Boardwalk and J.C. Lore Oyster House.

Washer

Dryer

Waterfront home with private dock near St. Michaels & Easton

Easton MD

Located in Easton, this vacation home is on the waterfront, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery.

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

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach MD

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

Kitchen

Washer

GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD

Bozman MD

Located in Bozman, this vacation home is on the waterfront, within a 15-minute drive of Neavitt Park and Perry Cabin Park.

Pool

Kitchen

Secluded Woodland Waterfront Retreat

Solomons MD

This vacation home is 1.3 mi (2.2 km) from Annmarie Sculpture Garden and Arts Center and 1.4 mi (2.2 km) from Southern Branch Library.

Hot Tub

Kitchen

Waterfront Getaway with Dock

Woolford MD

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

Kitchen

Washer

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

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

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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.