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 ...
9.6/10 Exceptional! (28 reviews)
The house was spacious and comfortable, a great fit for our work trip.
Reviewed on Mar 2, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$275 nightly
The price is $312 total per night from May 17 to May 18
$312 total
May 17 - May 18
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. ...
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$603 nightly
The price is $663 total per night from May 28 to May 29
$663 total
May 28 - May 29
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! (383 reviews)
Beautiful property and fantastic room with a water view.
Reviewed on May 7, 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 ...
9.6/10 Exceptional! (28 reviews)
The house was spacious and comfortable, a great fit for our work trip.
Reviewed on Mar 2, 2026
Soul Oasis - home on the Chesapeake Bay
Lusby MD
Stay at this cottage in Lusby. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Drum Point Lake and Cove Point Beach are located nearby.
10/10 Exceptional! (46 reviews)
It was a nice small A-frame just like the picture. Great quiet location I would recommend it to anyone.
Reviewed on Apr 21, 2026
Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman MD
Stay at this cottage in Wittman. Enjoy free WiFi, private pools, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (243 reviews)
Delightful, well-kept cottage.
Reviewed on May 1, 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
- Calvert Cliffs State Park
- Blackwater National Wildlife Refuge
- Northern Chesapeake Bay
- Chesapeake Bay Maritime Museum
- St. Michaels Winery
- Gerry Boyle Park at Great Marsh
- Harriet Tubman Underground Railroad National Historical Park
- Choptank River Lighthouse
- Avalon Theatre
- Cove Point Lighthouse
- Harriet Tubman Museum and Educational Center
- Long Wharf Park
- Layton's Chance Vineyard and Winery
- Dorchester County Visitors Center
- Talbot County Visitor Center
- Bill Burton Fishing Pier State Park
- Jefferson Patterson Park and Museum
- Drum Point Lighthouse
- Bruce Gabrielson's Surf Art Gallery and Museum
