Woolford Holidays from £887

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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

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was £1,063, price is now £887 per person
£887
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
7.6/10 Good! (592 reviews)
Room was not cleaned daily. When made a request, no one spoke English and hardly understood what I was saying. Bathroom was not cleaned at all during my stay.

Reviewed on 3 Jul 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was £2,959, price is now £2,218 per person
£2,218
per person
12 Aug - 19 Aug
found 1 day ago
Return flight included
London (LHR) to Salisbury (SBY)
9.4/10 Exceptional! (779 reviews)
This hotel was beyond my expectations, the King room had a beautiful balcony, which you could see some of the beach from, the bed and pillows were great! I loved that it actually had a refrigerator and dishwasher in it and microwave and Keurig. As well as a sectional sofa which had a pull out bed, the bathroom was spacious and beautiful! Family friendly. Was pleasantly surprised with all of the details and the staff. We were only there for 1 night - quick trip but definitely will return.

Reviewed on 30 Jun 2026

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was £1,833, price is now £1,544 per person
£1,544
per person
12 Aug - 19 Aug
found 1 day ago
Return flight included
London (LHR) to Salisbury (SBY)
8.8/10 Excellent! (1,018 reviews)
We had a fourth floor room. Our door was right by the elevator and our car was nearby. This was really convenient. The roof top pool was a nice change up from the beach. The front desk greeter were wonderfully helpful. Our room service for cleaning was responsive to our needs...The bed was really comfortable. Having a small working fridge and microwave was helpful for a multi day stay. Free coffee available in the lobby was unexpected, and a big win in my eyes.

Reviewed on 2 Jul 2026

Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
Price was £2,129, price is now £1,892 per person
£1,892
per person
12 Aug - 19 Aug
found 1 day ago
Return flight included
London (LHR) to Salisbury (SBY)
9.2/10 Wonderful! (1,458 reviews)
location, cleanliness

Reviewed on 2 Jul 2026

Harrison Hall Hotel

Harrison Hall Hotel

2 out of 5
Downtown Ocean City
Price was £1,048, price is now £932 per person
£932
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
London (LON) to Salisbury (SBY)
7.6/10 Good! (1,007 reviews)
Wow! Superb view of the ocean from the front office and covered porch. Friendly staff, perfect location to about anything you’d want, and beautiful time just a few steps out of the hotel.

Reviewed on 2 Jul 2026

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
Get rates
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! (76 reviews)
"We had an absolutely wonderful stay at this vacation rental! The property was amazing, and we had everything we needed for a relaxing getaway. The views of the bay were incredible, especially at sunrise and sunset.Communication with the owner was excellent from start to finish, and check-in/out was ..."

Reviewed on 18 May 2026

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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
Fully refundableReserve now, pay when you stay
The price is £290 per night from 6 Jul to 7 Jul
£290
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Dealing with billing issue. Other than that, great place to stay."

Reviewed on 26 Jun 2026

Hyatt Regency Chesapeake Bay
See all 543 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Woolford attractions

Woods Island

Commune with nature and explore the great outdoors at Woods Island during your travels in Woolford.
See properties

Frequently asked questions

How much does a Woolford travel package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Woolford from just £887. And the more you bundle, the more cash you save. The getaway of your dreams has never been more affordable.
If I'm not able to travel, can I cancel my Woolford travel package?
Don't worry if you're rethinking your Woolford travel package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We realise life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.
How do I get a cheap travel package to Woolford?
Secure flights that fit in with your schedule, add a hotel room to your booking and watch the savings grow with a Woolford holiday package. It's that simple! From hotels and flights to rental cars and tours, Expedia makes travelling cheaply a cinch. And with over 550 airlines and 1,000,000 hotel options throughout the world to choose from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later Woolford holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your holiday over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

What are the top hotels in Woolford?
Secure a room at Renaissance Baltimore Harborplace Hotel. It's one of the neighbourhood's most sought-after hotels. Another top-rated option in Woolford is Hyatt Regency Baltimore Inner Harbour.
How far in advance should I book my Woolford holiday?
Get rewarded with the widest variety at the cheapest prices by booking your adventure to Woolford early. Airlines typically sell flight tickets around a year before departure, so reserve your spot ASAP. Having said that, Expedia is dedicated to giving you the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Woolford travel package include?
Hotels, flights and rental cars — you'll find them all here. With Expedia, you can create your Woolford travel package the way you want. All you have to do is figure out what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the more you save!
What should I know before booking a Woolford travel package?
Whether it's relaxation or adventure you're seeking, a Woolford travel package lets you organise your escape your way. Plus, you'll get access to great discounts just for combining your accommodation with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Woolford Expedia travel package?
Yes, you're in charge. We have access to over 550 airlines across the globe, so you can design your Woolford trip according to your style and budget.

Explore a world of travel with Expedia

* 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.