Woolford Holiday Packages
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Top Woolford hotels
"Endless Summer" Waterfront on the Chesapeake Bay!
Woolford MD
"Endless Summer" Waterfront on the Chesapeake Bay!: Pet-friendly holiday home with an indoor pool and WiFi.
We had a great visit at “Endless Summer “. Everything was as advertised. House, pool and property were great. Enjoyed seeing eagles on the dock in the mornings. Communication with the host was timely and helpful.
Reviewed on 30 Dec 2025
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Woolford MD
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted: Family-friendly holiday home with free WiFi and an outdoor pool. Located on the waterfront.
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 1 Dec 2025
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: Pet-friendly holiday home with free WiFi and parking.
The house was spacious and comfortable, a great fit for our work trip.
Reviewed on 2 Mar 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.
