Book Holiday Homes in Woolford

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Featured Holiday Homes in Woolford

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 AU$610 per night from 16 Dec to 17 Dec
AU$610
includes taxes & fees
16 Dec - 17 Dec
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
The price is AU$802 per night from 1 Dec to 2 Dec
AU$802
includes taxes & fees
1 Dec - 2 Dec
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 8 minutes by car from Spocott Windmill.
Beautiful Waterfront Retreat in Cambridge!
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood
When you stay at this vacation home in Sherwood, you'll be on the waterfront and 7 minutes by car from Tilghman Watermen’s Museum.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Cottage on Cabin Creek

Cottage on Cabin Creek

Secretary
The price is AU$564 per night from 30 Nov to 1 Dec
AU$564
includes taxes & fees
30 Nov - 1 Dec
With a stay at this vacation home in East New Market, you'll be on the waterfront, and 11 mi (17.7 km) from Bay Country Shop and 12 mi (19.3 km) from Dorchester ...
Cottage on Cabin Creek
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 7.7 mi (12.4 km) from Spocott Windmill and 14 mi (22.5 km) from Richardson Maritime ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Waterfront  - pier & acreage to run & play.   Pet friendly Oct/Nov dates open!

Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!

Saint Michaels
Located in St. Michaels, this vacation home is on the waterfront, within a 15-minute drive of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
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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
213 Holiday Homes
Lowest Price
AU$145
Highest Price
AU$802
Popular accommodation
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Beautiful Waterfront Retreat in Cambridge!, Walk to Everything House, Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, Cottage on Cabin Creek, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!

Top trending hotels in Woolford

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

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

Woolford
A stay at this vacation home places you in the heart of Woolford, and within a 15-minute drive of Blackwater National Wildlife Refuge.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, 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 AU$369 per night from 2 Dec to 3 Dec
AU$369
includes taxes & fees
2 Dec - 3 Dec
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$533 per night from 17 Dec to 18 Dec
AU$533
includes taxes & fees
17 Dec - 18 Dec
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Inn at Perry Cabin
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St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$145 per night from 16 Dec to 17 Dec
AU$145
includes taxes & fees
16 Dec - 17 Dec
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
Don't see what you're looking for?
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.