Woolford Holidays from £1,172

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Your Woolford Holiday

Say bye-bye to the stress of planning and hello to a Woolford holiday package. With the finer details organised 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 holiday is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.

Top Woolford Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sahara Motel
Grand Hotel Ocean City Oceanfront
Ocean 1 Hotel and Suites
Ashore Resort & Beach Club
Princess Royale Oceanfront Resort

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

Top hotels in Woolford

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
9.6/10 Exceptional! (28 reviews)
The house was spacious and comfortable, a great fit for our work trip.

Reviewed on 2 Mar 2026

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

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

Woolford MD
9.8/10 Exceptional! (75 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

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
The price is £239 per night from 13 Apr to 14 Apr
£239
13 Apr - 14 Apr
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Friendly and helpful staff, pleasant and comfortable room, good food, convenient location and wonderful scenery.

Reviewed on 20 Mar 2026

Hyatt Regency Chesapeake Bay
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.