Book Holiday Homes in Woolford

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Featured Holiday Homes in Woolford

Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby
Stay at this vacation home in Lusby. Enjoy free WiFi, patios, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular attractions ...
Waterfront Wildlife Retreat on the Patuxent River
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels
Stay at this vacation home in St. Michaels. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Muskrat Park and Higgins Yacht Yard and ...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Stunning  Chesapeake view from almost ever room, private  15 home community beach, fossils, 450 pier

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

Port Republic
Book a stay at this beach vacation home in Port Republic. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Matoaka Beach and Long Beach are ...
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
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Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
Stay at this vacation home in Lusby. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Seahorse Beach and Drum Point Lake are located ...
Belle of the Chesapeake Bay
Tranquil  Beautiful Waterfront  Near Historic St. Michaels & Royal Oak

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

easton
Book a stay at this family-friendly vacation home in Easton. Enjoy free WiFi, a garden, and concierge services. Popular attractions Saint Michaels Village and ...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Walk to Everything House

Walk to Everything House

Saint Michaels
Stay at this vacation home in St. Michaels. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Muskrat Park and Clint ...
Walk to Everything House
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

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

2 out of 5
Cambridge
Stay at this vacation home in Cambridge. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Harriet Tubman Museum and Educational Center ...
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Serene Waterfront Minutes from St Michaels.

Serene Waterfront Minutes from St Michaels.

Easton
Stay at this vacation home in Easton. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Saint Michaels Village and Classic Motor Museum ...
Serene Waterfront Minutes from St Michaels.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
The price is NZ$705 per night from 20 Apr to 21 Apr
NZ$705
includes taxes & fees
20 Apr - 21 Apr
Stay at this vacation home in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Choptank River Lighthouse and Long Wharf Park ...
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City 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.

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
NZ$489
Highest Price
NZ$780
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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and patios. Popular attractions Woods Island and Harriet Tubman Underground Railroad National ...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Harriet Tubman Underground Railroad National ...
Waterfront Getaway with Dock
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is NZ$489 per night from 6 May to 7 May
NZ$489
includes taxes & fees
6 May - 7 May
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Hyatt Regency Chesapeake Bay
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Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is NZ$780 per night from 7 Apr to 8 Apr
NZ$780
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Inn at Perry Cabin
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See all available properties in Woolford
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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.