Book Holiday Homes in Woolford

Featured Holiday Homes in Woolford

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.

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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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Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Lusby MD

With a stay at this vacation home in Lusby, you'll be on a lake, within a 10-minute drive of Chesapeake Bay and Cove Point Park.

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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

St. Michaels MD

Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of St Michaels Nature Trail and Higgins Yacht Yard and Marina.

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Back Creek Villa Covered Deck

Solomons MD

With a stay at this vacation home in Solomons Island, you'll be within a 15-minute drive of Chesapeake Bay and J.C. Lore Oyster House.

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Dollhouse in Central Historic St Michaels

St Michaels MD

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

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"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD

When you stay at this vacation home in Woolford, you'll be 14 minutes by car from Blackwater National Wildlife Refuge.

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Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, within a 10-minute walk of Classic Motor Museum and Windon Distilling.

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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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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.

Woolford Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Woolford vacation homes are the perfect way for you to wing it.

Holiday houses in Woolford let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Woolford in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Woolford adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Woolford with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Woolford vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Woolford Holiday Homes essential information

Accommodation	257 Holiday Homes
Lowest Price	AU$377
Highest Price	AU$914
Popular accommodation	Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Minutes from Downtown St. Michaels \| Pool \| Hot Tub \| Private Dock, Back Creek Villa Covered Deck, Dollhouse in Central Historic St Michaels, "Endless Summer" Waterfront on the Chesapeake Bay!, Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels, Cottage with Private Water Access \| Pet-Friendly \| Near St. Michaels

Top trending hotels in Woolford

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 ...

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Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Fully refundableReserve now, pay when you stay

AU$408

17 May - 18 May

includes taxes & fees

Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital ...

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

AU$914

31 May - 1 June

includes taxes & fees

A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Perry Cabin Park and Saint Michaels Town Hall.

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The Wildset

209 N Talbot St St. Michaels MD

AU$377

26 May - 27 May

includes taxes & fees

With a stay at The Wildset in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town ...

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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.