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! (36 reviews)
"Lots of space for our group! Had a great sunroom where our kids all played. It was clean and we also appreciated how much was provided in the kitchen."
Reviewed on Oct 12, 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
$79 nightly
The price is $87 total per night from Dec 10 to Dec 11
$87 total
Dec 10 - Dec 11
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,006 reviews)
"Convenient to St Michael’s and inexpensive."
Reviewed on Nov 9, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$170 nightly
The price is $193 total per night from Nov 23 to Nov 24
$193 total
Nov 23 - Nov 24
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. ...
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! (36 reviews)
"Lots of space for our group! Had a great sunroom where our kids all played. It was clean and we also appreciated how much was provided in the kitchen."
Reviewed on Oct 12, 2026
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
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! (80 reviews)
"Everyone enjoyed the pool, dock, beach,screened in porch. They have two refrigerators, bike helmets, toddler toilet seat, step stool on third floor. Bring room darkening shades for anyone who likes to sleep late. Two baby gates for the stairs were wonderful. Bring sand toys and water shoes for all. ..."
Reviewed on Sep 1, 2026
Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge MD
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and a garden. Popular attractions Christ Rock Park and Spocott ...
9.6/10 Exceptional! (99 reviews)
"House was grateful and host was super responsive."
Reviewed on Oct 20, 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.
Stay near popular Woolford attractions
- Blackwater National Wildlife Refuge
- Chesapeake Bay
- Calvert Cliffs State Park
- Breezy Point Beach
- Patuxent River Naval Air Station
- St. Michaels Winery
- Northern Chesapeake Bay
- Cove Point Lighthouse
- Chesapeake Bay Maritime Museum
- Gerry Boyle Park at Great Marsh
- Choptank River Lighthouse
- Avalon Theatre
- Harriet Tubman Underground Railroad National Historical Park
- Patuxent River Naval Air Museum
- Harriet Tubman Museum and Educational Center
- Drum Point Lighthouse
- Long Wharf Park
- Dorchester County Visitors Center