Woolford Vacations

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Find the Best Woolford Vacation Packages

Woolford Hotel Deals

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 ₩356,559 per night from Jun 23 to Jun 24
₩356,559
₩476,457 total
Jun 23 - Jun 24
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 May 27, 2026

Hyatt Regency Chesapeake Bay
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 ₩203,540 per night from Jun 2 to Jun 3
₩203,540
₩223,895 total
Jun 2 - Jun 3
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Room was clean. Only complaint was AC blew directly into face when sleeping and there was no way to adjust vent."

Reviewed on May 29, 2026

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is ₩907,196 per night from Jun 21 to Jun 22
₩907,196
₩997,915 total
Jun 21 - Jun 22
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 May 22, 2026

Inn at Perry Cabin
See all 534 properties in Woolford
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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