Woolford Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Woolford
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
The price is €727 per night from 21 May to 22 May
€727
21 May - 22 May
includes taxes & fees
9.6/10 Exceptional! (28 reviews)
"The house was spacious and comfortable, a great fit for our work trip."
Reviewed on 2 Mar 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is €278 per night from 21 May to 22 May
€278
21 May - 22 May
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Hotel needs a big update. Very dated"
Reviewed on 17 May 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is €613 per night from 8 Jun to 9 Jun
€613
8 Jun - 9 Jun
includes taxes & fees
9.6/10 Exceptional! (386 reviews)
"Wonderful location with great views and amenities such as a fire pit"
Reviewed on 18 May 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
