Woolford Vacations from $645

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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.

The Latest Woolford vacation packages

Price found within the past 48 hours. Click for updated prices.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.6/10 Good! (63 reviews)
It doesn't have a gym, it doesn't have free breakfast, it doesn't have bike rentals, or free water bottles or a cookies when you check in. But it's a clean, well-run establishment in a perfect location. I would highly recommend if you're visiting Ocean City.

Reviewed on Jun 25, 2025

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.8/10 Exceptional! (248 reviews)
Clean and convenient with close access to beach and restaurants.

Reviewed on Jun 24, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (2,932 reviews)
Everything was great except the elevator situation.

Reviewed on Jun 27, 2025

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Salisbury (SBY)
7.2/10 Good! (150 reviews)
The property itself was good, a little dated but clean otherwise. The three women working the desk were the best part. They were very kind and accommodating to my family. The only part that was not so good was the small print from expedia about this being a timeshare property as we had to change rooms mid trip.

Reviewed on Jun 17, 2025

Americana Princess Suites and Condos

Americana Princess Suites and Condos

2.5 out of 5
Downtown Ocean City
per person
Aug 17 - Aug 21
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
7.2/10 Good! (15 reviews)
This is a decent place to stay. Very walkable. Condo is a nice size! Plenty of room for 2 families of 3. Had a plumbing issue and the staff addressed it very quickly! Would stay here again.

Reviewed on Jun 8, 2025

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Woolford Hotel Deals

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.8/10 Exceptional! (10 reviews)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected."

Reviewed on Jun 6, 2025

Get rates
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $292 total per night from Jul 22 to Jul 23
$292 total
Jul 22 - Jul 23
Total includes taxes and fees
8.6/10 Excellent! (1,001 reviews)
"The Hyatt is a great stay. Balconies outside need painting. Staff and amenities otherwise are great."

Reviewed on Jun 22, 2025

Hyatt Regency Chesapeake Bay
Solomons Inn Resort & Marina
Solomons Inn Resort & Marina
2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $148 total per night from Jul 6 to Jul 7
$148 total
Jul 6 - Jul 7
Total includes taxes and fees
7.8/10 Good! (811 reviews)
Fabulous
"Wonderful stay for my friends birthday.Janai at front desk was exceptional in getting birthday care for the room and assuring a waterfront room. Janai and my friend shared the same birthday. Everyone was so nice and accommodating. Will be my new getaway spot."

Reviewed on Jun 24, 2025

Solomons Inn Resort & Marina
See all 518 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.

Find the Best Woolford Vacation Packages

Woolford Essential Information

Language
English
Currency
U.S dollars
Top Sights
Bill Burton Fishing Pier State Park, Choptank River Lighthouse and Great Marsh Park

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Frequently asked questions

How much does a Woolford vacation package cost?
You can pick up a vacation package to this popular destination from $645 on Expedia. But how much your vacation to Woolford costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Woolford?
November, December and January are great times to search for cheap Woolford vacation packages. Choosing to travel in quieter periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Woolford?
With a well-organized travel plan, you can easily hit the most popular Woolford sights in a handful of days. But if you want to explore off the beaten track or go on day trips, consider booking your Woolford vacation for longer.
How to find the best Woolford package deals?
Use Expedia's filters to find some unbeatable Woolford package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Woolford package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Woolford vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Woolford trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Woolford?
Land amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Woolford vacation.
Does Expedia offer Book Now, Pay Later Woolford vacation packages?
If you're like us, you love traveling the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Woolford break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.