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
$197 nightly
The price is $224 total per night from Jan 1 to Jan 2
$224 total
Jan 1 - Jan 2, 2026
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)
The property was marketed as luxury but it's far from it. My headboard was shredded. Bathtub had hair. Heating was inconsistent
Reviewed on Dec 21, 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)
Incredible stay!!! What a special place! We loved this house and would definitely stay again! It was perfect for multiple families. It was great for our kids too! Lots of activities for them including basketball, shuffleboard, and kayaking! We would recommend renting this house!
Reviewed on Dec 2, 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
- St. Michaels Winery
- Harriet Tubman Underground Railroad National Historical Park
- Choptank River Lighthouse
- Gerry Boyle Park at Great Marsh
- Avalon Theatre
- Chesapeake Bay Maritime Museum
- Dorchester County Visitors Center
- Cove Point Lighthouse
- Northern Chesapeake Bay
- Harriet Tubman Museum and Educational Center
- Long Wharf Park
- Drum Point Lighthouse
- Patuxent River Naval Air Museum
- Bruce Gabrielson's Surf Art Gallery and Museum
