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
The price is $296 total per night from May 17 to May 18
$296 total
per night
May 17 - May 18
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
The price is $663 total per night from May 31 to Jun 1
$663 total
per night
May 31 - Jun 1
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! (385 reviews)
We had yet another wonderful stay, great views, very comfortable. Some areas (primarily outside) would benefit from some paint.
Reviewed on May 14, 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
"Endless Summer" Waterfront on the Chesapeake Bay!
Woolford MD
Stay at this vacation home in Woolford. Enjoy private pools, laundry facilities, and patios. Popular attractions Ragged Island and Spocott Windmill are located ...
10/10 Exceptional! (8 reviews)
We came for a short weekend get-a-way and the Endless Summer certainly provided exactly what we needed. It was peaceful, quiet and absolutely beautiful. The house is huge and would definitely work for a large family gathering. The bedroom layout is really nice for privacy. It was too cold to test ...
Reviewed on May 1, 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
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
- Blackwater National Wildlife Refuge
- Breezy Point Beach
- Calvert Cliffs State Park
- Chesapeake Bay Maritime Museum
- Northern Chesapeake Bay
- St. Michaels Winery
- Harriet Tubman Underground Railroad National Historical Park
- Gerry Boyle Park at Great Marsh
- Choptank River Lighthouse
- Avalon Theatre
- Harriet Tubman Museum and Educational Center
- Long Wharf Park
- Cove Point Lighthouse
- Layton's Chance Vineyard and Winery
- Dorchester County Visitors Center
- Talbot County Visitor Center
- Jefferson Patterson Park and Museum
- Bill Burton Fishing Pier State Park
- Drum Point Lighthouse
- Bruce Gabrielson's Surf Art Gallery and Museum