Woolford, MD
Travel Guide
Visit Woolford
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$296 nightly
The price is $336 total per night from Jul 7 to Jul 8
$336 total
Jul 7 - Jul 8
Total with taxes and fees
Book a stay at this 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. ...
8.8/10 Excellent! (1,002 reviews)
"We loved staying here! Incredible staff!"
Reviewed on Jun 22, 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$720 nightly
The price is $792 total per night from Jul 9 to Jul 10
$792 total
Jul 9 - Jul 10
Total with taxes and fees
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. ...
9.6/10 Exceptional! (390 reviews)
"It was a wonderful stay. The rooms were clean, the staff helpful and the food marvelous. I intend to visit again!"
Reviewed on Jun 8, 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.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Woolford MD
Book a stay at this beach vacation home in Woolford. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Ragged Island and Spocott Windmill ...
9.8/10 Exceptional! (76 reviews)
"We had an absolutely wonderful stay at this vacation rental! The property was amazing, and we had everything we needed for a relaxing getaway. The views of the bay were incredible, especially at sunrise and sunset.Communication with the owner was excellent from start to finish, and check-in/out was ..."
Reviewed on May 18, 2026
Grace Cottage, St Michaels Walk to everything!
Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (7 reviews)
"This was an AMAZING fine. Grace cottage was so perfectly located where literally everything is walkable and convenient parking for 2 cars. The host, Lisa, was so responsive and just the sweetest. It is clear they want you to have a wonderful time with the cottage being stocked with almost anything ..."
Reviewed on Jun 21, 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.
Popular places to visit
Woods Island
Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford.
- Chesapeake Bay
- Patuxent River Naval Air Station
- Breezy Point Beach
- Blackwater National Wildlife Refuge
- Gerry Boyle Park at Great Marsh
- Calvert Cliffs State Park
- Northern Chesapeake Bay
- Avalon Theatre
- Chesapeake Bay Maritime Museum
- St. Michaels Winery
- Harriet Tubman Underground Railroad National Historical Park
- Long Wharf Park
- Patuxent River Naval Air Museum
- Harriet Tubman Museum and Educational Center
- Drum Point Lighthouse
- Historical Society of Talbot County
- Choptank River Lighthouse
- Harriet Tubman Birthplace Marker
- Cove Point Lighthouse
