Woolford Holidays
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Woolford Holiday
Our pick of the best Woolford Hotel Deals
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
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 NZ$625 per night from 1 June to 2 June
NZ$625
1 June - 2 June
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Hotel is beautiful , grounds are beautiful ! Staff is amazing ! Only disappointment was the pool situation - Seems like if you are there during the week or if weather isn’t perfect restaurants and amenities aren’t available as expected. It wasn’t raining just overcast, and it was warm and humid out ..."
Reviewed on 27 May 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is NZ$1,201 per night from 21 June to 22 June
NZ$1,201
21 June - 22 June
includes taxes & fees
9.6/10 Exceptional! (387 reviews)
"We enjoyed a wonderful, stress-free four days at the inn and the surrounding area. Highly recommend it."
Reviewed on 22 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
