Book Holiday Homes in Woolford
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Featured Holiday Homes in Woolford

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

Heated pool, sandy beach, pier, and playground set punch point apart!

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Rising Sun Bay View Cottage

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

St. Michaels Waterfront Home

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

Waterfront Wildlife Retreat on the Patuxent River

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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 | 281 Holiday Homes |
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Lowest Price | AU$215 |
Highest Price | AU$627 |
Popular accommodation | Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Heated pool, sandy beach, pier, and playground set punch point apart!, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Rising Sun Bay View Cottage, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, St. Michaels Waterfront Home, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Waterfront Wildlife Retreat on the Patuxent River , Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina |
Top trending hotels in Woolford

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Hyatt Regency Chesapeake Bay

Solomons Inn Resort & Marina

The Wildset
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^Subject to availability and chosen travel dates.