Woolford Vacation Rentals

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Vacation Rentals in Woolford

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, steps from Muskrat Park and Saint Marys Square.

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Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD

With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.

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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.

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Shewell's A-Frame on Mill Creek

Lusby MD

With a stay at this vacation home in Lusby, you'll be within a 5-minute drive of Chesapeake Bay and Drum Point Lake.

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Cottage with Private Water Access | Pet-Friendly | Near St. Michaels

Neavitt MD

When you stay at this vacation home in Neavitt, you'll be 6 minutes by foot from Neavitt Park.

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Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton MD

With a stay at this vacation home in Easton, you'll be on the beach, and 24.8 mi (40 km) from Chesapeake Bay and 6.7 mi (10.7 km) from Avalon Theatre.

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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.

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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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Stunning views at WATERFRONT St Michaels area historic home, dog friendly

Neavitt MD

When you stay at this vacation home in Neavitt, you'll be on the waterfront and 3 minutes by foot from Neavitt Park.

The Blackwater refuge country house on a quiet 12 acres

Crapo MD

When you stay at this vacation home in Church Creek, you'll be within a short 3-minute drive from Blackwater National Wildlife Refuge.

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Dryer

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

Port Republic MD

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

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Modern Chesapeake Waterfront - Heated Pool - Dock

Cambridge MD

With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

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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.