Woolford Vacation Rentals

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Vacation Rentals in Woolford

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Fishing Creek MD

With a stay at this vacation home in Fishing Creek, you'll be on the waterfront, within a 10-minute drive of Chesapeake Bay and P. L. Jones Marina.

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.

Kitchen

Washer

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard MD

$260 nightly

$276 total

Aug 31 - Sep 1

Total with taxes and fees

With a stay at this vacation home in St. Leonard, you'll be a 5-minute walk from Chesapeake Bay and 5 minutes by foot from Flag Harbor Marina.

Kitchen

Washer

Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing

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.

Belle of the Chesapeake Bay

Lusby MD

With a stay at this vacation home in Lusby, you'll be a 1-minute drive from Chesapeake Bay and 7 minutes from Cove Point Park.

Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels

Tilghman Island MD

Located in Tilghman, this vacation home is in a rural location, within a 15-minute walk of Kronsberg Park and Phillips Wharf Environmental Center.

Private Chesapeake Bay Beach community…love to feel the sand between your toes?

Port Republic MD

When you stay at this vacation home in Port Republic, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

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.

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lusby MD

$814 nightly

$863 total

Aug 24 - Aug 25

Total with taxes and fees

With a stay at this vacation home in Lusby, you'll be a 5-minute drive from Chesapeake Bay and 6 minutes from Chesapeake Hills Golf Course.

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.

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.

Cozy Cedar Cottage-Beach Getaway

St Leonard MD

When you stay at this vacation home in St. Leonard, you'll be near the beach, within a 10-minute walk of Chesapeake Bay and Flag Harbor Marina.

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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.