Woolford Vacation Rentals

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Vacation Rentals in Woolford

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.

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.

Waterfront Wildlife Retreat on the Patuxent River

Lusby MD

Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Chesapeake Bay.

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.

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.

A breathtaking secluded luxury waterfront cottage, complete with a private pier.

Lusby MD

Located in Lusby, this vacation home is on the waterfront, within a 10-minute drive of Calvert Cliffs State Park and Drum Point Lake.

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.

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of 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.

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.

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford MD

Located in Oxford, this vacation home is on the waterfront, within a 10-minute drive of Play Ball Dog Park and Oxford Museum.

Thorneton Point Estate

Easton MD

Located in Easton, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.

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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.