Woolford, MD
Travel Guide
Visit Woolford
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford
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)
We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.
Reviewed on Aug 24, 2025
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
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! (20 reviews)
Family vacation
The home was spacious and clean. We appreciated the comfortable beds and linens.The kitchen is well stocked and functions well.Simply and nicely decorated.We looked forward to kayaking and enjoyed that, but,it is quite mushy getting down and into the water. We went to all the recommended locations ...
Reviewed on Aug 7, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd, Cambridge, MD
$184 nightly
The price is $209 total per night from Nov 23 to Nov 24
$209 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this 4-star 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! (1,014 reviews)
The room was spotless. The staff were courteous and helpful. Fantastic hotel!
Reviewed on Oct 28, 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
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! (20 reviews)
Family vacation
The home was spacious and clean. We appreciated the comfortable beds and linens.The kitchen is well stocked and functions well.Simply and nicely decorated.We looked forward to kayaking and enjoyed that, but,it is quite mushy getting down and into the water. We went to all the recommended locations ...
Reviewed on Aug 7, 2025
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford
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)
We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.
Reviewed on Aug 24, 2025
Waterfront Solomons Apartment
Solomons
Book a stay at this family-friendly apartment in Solomons. Enjoy free WiFi, laundry facilities, and patios. Popular attractions J.C. Lore Oyster House and Solomons ...
9/10 Wonderful! (13 reviews)
The place was very cute and love the location. Owner and maintenance were very responsive to my needs. It was pretty clean for the most part, other than afew things left in trash in bathroom. Dryer didn’t work. Small things, but overall great stay!! Would stay again!
Reviewed on Oct 14, 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
- Calvert Cliffs State Park
- Breezy Point Beach
- Blackwater National Wildlife Refuge
- St. Michaels Winery
- Choptank River Lighthouse
- Chesapeake Bay Maritime Museum
- Cove Point Lighthouse
- Harriet Tubman Underground Railroad National Historical Park
- Long Wharf Park
- Harriet Tubman Museum and Educational Center
- Gerry Boyle Park at Great Marsh
- Avalon Theatre
- Dorchester County Visitors Center
- Jefferson Patterson Park and Museum
- Drum Point Lighthouse
- Annmarie Sculpture Garden and Arts Center
- Talbot County Visitor Center
- Patuxent River Naval Air Museum
- Bill Burton Fishing Pier State Park
- Layton's Chance Vineyard and Winery