Book Holiday Homes in Woolford

Start date: Check-in selected.
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Woolford

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
Stay at this vacation home in Cambridge. Enjoy free WiFi, private pools, and a garden. Popular attractions Spocott Windmill and Brannock Maritime Museum are ...
Opens in a new windowNEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
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$684 per night from 1 Oct to 2 Oct
NZ$684
1 Oct - 2 Oct
includes taxes & fees
Stay at this vacation home in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Choptank River Lighthouse and Long Wharf Park ...
Opens in a new windowCozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
Book a stay at this family-friendly vacation home in Royal Oak. Enjoy free WiFi, private pools, and a garden. Popular attractions Royston Island and Oxford Museum ...
Opens in a new windowRANCH AT ROYAL OAK- Exclusive waterfront pool pier
Save an average of 15% on thousands of hotels when you're signed in
4BDRM River front house with Private Beach in Hollywood

4BDRM River front house with Private Beach in Hollywood

2 out of 5
Hollywood
Book a stay at this beach vacation home in Hollywood. Enjoy a beach locale, laundry facilities, and an in-room coffeemaker. Popular attractions Myrtle Point ...
Opens in a new window4BDRM River front house with Private Beach in Hollywood
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

3 out of 5
East New Market
Stay at this 3-star family-friendly vacation home in East New Market. Enjoy free WiFi, private pools, and a garden. Popular attractions Bill Burton Fishing Pier ...
Opens in a new window"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
Stay at this vacation home in St. Michaels. Enjoy free WiFi, 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
Single family home with screened porch.

Single family home with screened porch.

Fishing Creek
Stay at this vacation home in Fishing Creek. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions P. L. Jones Marina and Gunners Island are ...
Opens in a new windowSingle family home with screened porch.
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
The price is NZ$732 per night from 24 Sept to 25 Sept
NZ$732
24 Sept - 25 Sept
includes taxes & fees
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Spocott Windmill and ...
Opens in a new windowBeautiful Waterfront Retreat in Cambridge!
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 laundry facilities. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
Opens in a new windowDowntown St. Michaels | Walk to Shops, Restaurants and Nightlife
Don't see what you're looking for?
See all available properties in Woolford
View all properties
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
280 Holiday Homes
Lowest Price
NZ$173
Highest Price
NZ$732
Popular accommodation
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, 4BDRM River front house with Private Beach in Hollywood, "Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!, Dollhouse in Central Historic St Michaels, Single family home with screened porch. , Beautiful Waterfront Retreat in Cambridge!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Top trending hotels in Woolford

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

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

Woolford
Book a stay at this beach vacation home in Woolford. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Ragged Island and Spocott Windmill ...
Opens in a new window Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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 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
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is NZ$173 per night from 1 Oct to 2 Oct
NZ$173
1 Oct - 2 Oct
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowSt Michaels Inn
Save an average of 15% on thousands of hotels when you're signed in
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$445 per night from 1 Oct to 2 Oct
NZ$445
1 Oct - 2 Oct
includes taxes & fees
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. ...
Opens in a new windowHyatt Regency Chesapeake Bay
Don't see what you're looking for?
See all available properties in Woolford
View all properties
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.