Book Holiday Homes in Woolford
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Featured Holiday Homes in Woolford

Waterfront Wildlife Retreat on the Patuxent River

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

Belle of the Chesapeake Bay

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Walk to Everything House

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Serene Waterfront Minutes from St Michaels.

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 | 255 Holiday Homes |
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Lowest Price | AU$444 |
Highest Price | AU$853 |
Popular accommodation | Waterfront Wildlife Retreat on the Patuxent River , Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Belle of the Chesapeake Bay, Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak, Walk to Everything House, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Serene Waterfront Minutes from St Michaels., Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina |
Top trending hotels in Woolford

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Waterfront Getaway with Dock

Hyatt Regency Chesapeake Bay

Inn at Perry Cabin
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.