Book Holiday Homes in Woolford

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Featured Holiday Homes in Woolford

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.
Opens in a new windowPrivate 2 Acre Waterfront Family Retreat with Pool & Pier
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Lusby MD
Located in Lusby, this vacation home is a 5-minute drive from Chesapeake Bay and 6 minutes from Chesapeake Hills Golf Course.
Opens in a new windowMid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby MD
Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Chesapeake Bay.
Opens in a new windowWaterfront Wildlife Retreat on the Patuxent River
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Grace Cottage, Saint Michaels Walk to everything!

Grace Cottage, Saint Michaels Walk to everything!

Saint Michaels MD
With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and Saint Marys Square.
Opens in a new windowGrace Cottage, Saint Michaels Walk to everything!
Back Creek Villa Covered Deck

Back Creek Villa Covered Deck

Solomons MD
With a stay at this vacation home in Solomons Island, you'll be just steps from Solomons Island Boardwalk and J.C. Lore Oyster House.
Opens in a new windowBack Creek Villa Covered Deck
A breathtaking secluded luxury waterfront cottage, complete with a private pier.

A breathtaking secluded luxury waterfront cottage, complete with a private pier.

Lusby MD
Located in Lusby, this vacation home is on the waterfront, within a 10-minute drive of Calvert Cliffs State Park and Drum Point Lake.
Opens in a new windowA breathtaking secluded luxury waterfront cottage, complete with a private pier.
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison MD
Located in Madison, this vacation home is on the waterfront, within a 15-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad ...
Opens in a new windowAmazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Shewell's A-Frame on Mill Creek

Shewell's A-Frame on Mill Creek

Lusby MD
Located in Lusby, this vacation home is within a 5-minute drive of Drum Point Lake and Chesapeake Bay.
Opens in a new windowShewell's A-Frame on Mill Creek
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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
AU$366
Highest Price
AU$366
Popular accommodation
Private 2 Acre Waterfront Family Retreat with Pool & Pier, Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR, Waterfront Wildlife Retreat on the Patuxent River , Grace Cottage, Saint Michaels Walk to everything!, Back Creek Villa Covered Deck, A breathtaking secluded luxury waterfront cottage, complete with a private pier., Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Shewell's A-Frame on Mill Creek

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
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
 Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

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

Woolford MD
A stay at this vacation home places you in the heart of Woolford, and within 12 minutes by car from Blackwater National Wildlife Refuge.
Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
When you stay at this vacation home in Woolford, you'll be 14 minutes by car from Blackwater National Wildlife Refuge.
Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
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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 AU$366 per night from 24 Mar to 25 Mar
AU$366
24 Mar - 25 Mar
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital ...
Opens in a new windowHyatt Regency Chesapeake Bay
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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.