Woolford Holidays

Name: Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Rating: 9.8

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Your Woolford Holiday

Say goodbye to the stress of planning and hello to a Woolford holiday package. With the finer details organised before you leave, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is great for cafes, shopping and dining. Searching for some sightseeing ideas for your trip to Woolford? Harriet Tubman Underground Railroad National Historical Park and Spocott Windmill are two popular attractions here. Whatever your travel plans or the size of your budget, organising your ultimate tailored Woolford holiday is a walk in the park with Expedia.

Woolford Holiday

Woolford Essential Information

Language	English
Currency	U.S dollars
Max Temp Winter	7ºC
Max Temp Summer	27ºC
Top Sights	Bill Burton Fishing Pier State Park, Choptank River Lighthouse and Great Marsh Park

Our pick of the best Woolford Hotel Deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD

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 Oct 2025

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

Woolford MD

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 1 Dec 2025

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Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Fully refundableReserve now, pay when you stay

AU$404

1 Jan - 2 Jan 2026

includes taxes & fees

8.6/10 Excellent! (1,002 reviews)

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

See all 523 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.