Woolford Vacations from $1,223
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
The Latest Woolford vacation packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk One
Downtown Ocean City
Price was $1,399, price is now $1,223 per person
$1,223
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.4/10 Good! (164 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.
Reviewed on Oct 1, 2025
Bay Club Resort by Coolvacay
Midtown Ocean City
Price was $1,845, price is now $1,588 per person
$1,588
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.2/10 Very Good! (38 reviews)
I loved the dock and the gorgeous sunsets .
Reviewed on Sep 7, 2025
OCHG Ocean Block 7-11
Downtown Ocean City
Price was $2,000, price is now $1,722 per person
$1,722
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8/10 Very Good! (3 reviews)
The house was clean and spacious. The kitchen was well stocked with plates, cups, mugs, and silverware but other than that it was pretty bare bones throughout. From reading reviews beforehand, we brought a lot of items with us which helped a lot- towels, hand soap, oven mitts, cooking supplies, laundry detergent, dishwasher detergent, etc. Some of the furniture is falling apart but the house was very clean and the beds were comfortable and it was great having 2 bathrooms and the layout is spacious and we were able to walk to the festival grounds at the end of the boardwalk. If you bring the extra items you need and aren’t looking for luxury, then it’s a great place to stay and it’s right off the boardwalk and with free parking.
Reviewed on Sep 29, 2025
Miramar Condominiums
Downtown Ocean City
Price was $1,954, price is now $1,688 per person
$1,688
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!
Reviewed on Aug 23, 2025
OCHG VIRGINIA LEE
Downtown Ocean City
Price was $1,834, price is now $1,597 per person
$1,597
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.4/10 Very Good! (7 reviews)
We absolutely loved our stay at the OCHG Virginia Lee! We stayed in the top unit and it was amazing! The property manager, Cindy, is top notch and super quick with communication! Highly recommended!
Reviewed on Aug 3, 2025
Woolford Hotel Deals
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford
9.8/10 Exceptional! (58 reviews)
"We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family."
Reviewed on Aug 24, 2025
St Michaels Inn
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$92 nightly
The price is $102 total per night from Oct 19 to Oct 20
$102 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"Room was clean, Staff was very friendly and welcoming."
Reviewed on Oct 6, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $265 total per night from Oct 12 to Oct 13
$265 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Hyatt regency is more like a Hyatt place … fewer people working , in room dining is in paper boxes with plastic cutlery , but still regency pricing . But excellent pet policy and everyone so kind to pets"
Reviewed on Oct 3, 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.
Woolford Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Bill Burton Fishing Pier State Park, Choptank River Lighthouse and Great Marsh Park |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
