Book Holiday Homes in Woolford

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Featured Holiday Homes in Woolford

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
Stay at this holiday home in Tilghman. Enjoy a garden, laundry facilities and balconies. Popular attractions Tilghman Watermen’s Museum and Talbot County Library ...
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

Cambridge MD
Stay at this holiday home in Cambridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ragged Island and Spocott Windmill are located ...
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

Lusby MD
Stay at this holiday home in Lusby. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Drum Point Lake and Cove Point Beach are located ...
Opens in a new windowBay view from Calvert Cliffs, Solomons Island & State Park nearby
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Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

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

St. Michaels MD
Stay at this holiday home in St. Michaels. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Back Creek Park and Clint S. Bradley Park ...
Opens in a new windowMinutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Back Creek Villa Covered Deck

Back Creek Villa Covered Deck

Solomons MD
Stay at this holiday home in Solomons Island. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Solomons Island Boardwalk ...
Opens in a new windowBack Creek Villa Covered Deck
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels MD
Stay at this holiday home in St. Michaels. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Muskrat Park and Clint S. Bradley Park are ...
Opens in a new windowDollhouse in Central Historic St Michaels
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
Stay at this holiday home in Woolford. Enjoy private pools, laundry facilities and patios. Popular attractions Ragged Island and Spocott Windmill are located ...
Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Saint Michaels MD
Stay at this holiday home in St. Michaels. Enjoy a garden, laundry facilities and balconies. Popular attractions Church Cove Park and Classic Motor Museum are ...
Opens in a new windowBeautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels
Cottage with Private Water Access | Pet-Friendly | Near St. Michaels

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels

Neavitt MD
Stay at this holiday home in Neavitt. Enjoy balconies, an in-room coffee maker and air conditioning. Popular attractions Neavitt Park and Phillips Wharf Environmental ...
Opens in a new windowCottage with Private Water Access | Pet-Friendly | Near St. Michaels
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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
249 Holiday Homes
Lowest Price
NZ$460
Highest Price
NZ$1,117
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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Stay at this holiday home in Woolford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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$499 per night from 17 May to 18 May
NZ$499
17 May - 18 May
includes taxes & fees
Stay at this beach resort in Cambridge. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowHyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is NZ$1,117 per night from 31 May to 1 June
NZ$1,117
31 May - 1 June
includes taxes & fees
Stay at this luxury hotel in St. Michaels. Enjoy free Wi-Fi, free valet parking and a full-service spa. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowInn at Perry Cabin
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The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
The price is NZ$460 per night from 26 May to 27 May
NZ$460
26 May - 27 May
includes taxes & fees
Stay at this hotel in St. Michaels. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowThe Wildset
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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.

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^Subject to availability and chosen travel dates.