Name: The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Rating: 9.4

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Your Woolford Vacation

Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out Harriet Tubman Underground Railroad National Historical Park, Spocott Windmill and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.

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Woolford Hotel Deals

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 Dec 1, 2025

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD

9.4/10 Exceptional! (25 reviews)

Comfortable house near Cambridge for a three day stay. Would stay again!

Reviewed on Dec 14, 2025

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Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Fully refundableReserve now, pay when you stay

CA $253

CA $326 total

Feb 22 - Feb 23

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Nice stay, but a little too crowded.

Reviewed on Jan 30, 2026

See all 520 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.