Woolford Holiday Packages
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Top Woolford hotels
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford MD
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock: Family-friendly holiday home with free WiFi and an outdoor pool. Located in the city centre.
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.
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 Oct 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is AU$406 per night from 1 Jan to 2 Jan
AU$406
1 Jan - 2 Jan 2026
includes taxes & fees
Hyatt Regency Chesapeake Bay: Family-friendly resort with free WiFi and free parking. Located on the waterfront.
Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.
Reviewed on 5 Dec 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.
