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 ...
9.4/10 Exceptional! (21 reviews)
House was wonderful, it had something for all ages, plenty of room for our group of 17. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions ...
Reviewed on Oct 20, 2025
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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! (58 reviews)
The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again!
Reviewed on Dec 1, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$201 nightly
The price is $229 total per night from Dec 15 to Dec 16
$229 total
Dec 15 - Dec 16
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. ...
8.6/10 Excellent! (1,002 reviews)
Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.
Reviewed on Dec 5, 2025
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 ...
9.4/10 Exceptional! (21 reviews)
House was wonderful, it had something for all ages, plenty of room for our group of 17. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions ...
Reviewed on Oct 20, 2025
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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! (58 reviews)
The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again!
Reviewed on Dec 1, 2025
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Cambridge MD
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Spocott Windmill ...
9.8/10 Exceptional! (64 reviews)
There were so many activities and so many beds/baths. Perfect for a large group.
Reviewed on Nov 1, 2025
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
- Calvert Cliffs State Park
- Breezy Point Beach
- Harriet Tubman Underground Railroad National Historical Park
- St. Michaels Winery
- Cove Point Lighthouse
- Choptank River Lighthouse
- Gerry Boyle Park at Great Marsh
- Chesapeake Bay Maritime Museum
- Avalon Theatre
- Northern Chesapeake Bay
- Long Wharf Park
- Harriet Tubman Museum and Educational Center
- Dorchester County Visitors Center
- Patuxent River Naval Air Museum
- Bruce Gabrielson's Surf Art Gallery and Museum
- Drum Point Lighthouse
- Academy of the Arts
- Bill Burton Fishing Pier State Park