Woolford Holiday Packages
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Top Woolford hotels
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: Pet-friendly holiday home with free WiFi and parking.
The house was spacious and comfortable, a great fit for our work trip.
Reviewed on 2 Mar 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
Inn at Perry Cabin: Luxury hotel with free WiFi and free valet parking. Located on the waterfront.
Food, drinks and staff were all awesome. They had good bikes to borrow and ride into town on if you wanted, “don’t worry about locking them, nobody will take them”. They also would drive you, and pick you up if you wanted a ride to town. Everything about the experience was 1st class. Room was very ...
Reviewed on 11 Apr 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
Hyatt Regency Chesapeake Bay: Family-friendly resort with free WiFi and free parking. Located on a river.
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.
