Woolford, MD

Travel Guide

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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 24 August 2025

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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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! (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 20 October 2025

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundable
The price is AED 614 per night from Dec 15 to Dec 16
AED 614
AED 796 total
15 Dec - 16 Dec
includes taxes & 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! (1,000 reviews)
The room was spotless. The staff were courteous and helpful. Fantastic hotel!

Reviewed on 28 October 2025

Hyatt Regency Chesapeake Bay
See all 513 properties in Woolford
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

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! (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 20 October 2025

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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 24 August 2025

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Waterfront Solomons Apartment

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 14 October 2025

Waterfront Solomons Apartment
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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.

Woods Island