Book Holiday Homes in Woolford
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Featured Holiday Homes in Woolford
Dollhouse in Central Historic St Michaels
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Walk to Everything House
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Beautiful Peaceful Home
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Cottage on Cabin Creek
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 | 211 Holiday Homes |
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Lowest Price | NZ$167 |
Highest Price | NZ$782 |
Popular accommodation | Dollhouse in Central Historic St Michaels, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Walk to Everything House, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Beautiful Peaceful Home, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Cottage on Cabin Creek |
Top trending hotels in Woolford
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin
St Michaels Inn
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^Subject to availability and chosen travel dates.