Book Holiday Homes in Woolford

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

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

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

Cambridge
Stay at this vacation home in Cambridge. Enjoy private pools, patios, and cable/satellite TV service. Popular attraction Ragged Island is located nearby.
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
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
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard
Book a stay at this family-friendly vacation home in St. Leonard. Enjoy free WiFi, a garden, and a pool table. Popular attractions Jefferson Patterson Park and ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Save an average of 15% on thousands of hotels when you're signed in
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
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Cambridge
Stay at this vacation home in Cambridge. Enjoy private pools, a pool table, and patios. Popular attraction Ragged Island is located nearby.
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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
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 Lusby Retreat w/ Deep-Water Dock & Slip

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Lusby
Stay at this vacation home in Lusby. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Seahorse Beach and Annmarie Sculpture Garden ...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

St. Michaels
Stay at this vacation home in St. Michaels. Enjoy free WiFi, private pools, and a spa tub. Popular attractions Saint Michaels Village and Classic Motor Museum ...
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
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
204 Holiday Homes
Lowest Price
NZ$152
Highest Price
NZ$702
Popular accommodation
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Walk to Everything House, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Waterfront Lusby Retreat w/ Deep-Water Dock & Slip, Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

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
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$441 per night from 15 Mar to 16 Mar
NZ$441
includes taxes & fees
15 Mar - 16 Mar
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
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is NZ$702 per night from 26 Feb to 27 Feb
NZ$702
includes taxes & fees
26 Feb - 27 Feb
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
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$152 per night from 9 Mar to 10 Mar
NZ$152
includes taxes & fees
9 Mar - 10 Mar
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 ...
St Michaels Inn
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.