Woolford Vacations from $595

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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.
Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
Price was $702, price is now $595 per person
$595
per person
Oct 9 - Oct 12
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (1,506 reviews)
The hotel was great, if I had to go back I would definitely stay again. Really great that it was pet friendly. But the hotel rooms were pretty dirty and it was not the housekeepers fault. They did not have the right equipment to do it. For example a vacuum for the rooms nor the right cleaning products. Again this wouldn’t deter me from staying again but would like the hotel to take a little bit more pride in their rooms.

Reviewed on Aug 22, 2025

Americana Princess Suites and Condos

Americana Princess Suites and Condos

2.5 out of 5
Downtown Ocean City
Price was $1,118, price is now $893 per person
$893
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $905, price is now $766 per person
$766
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,117 reviews)
I loved this place and can’t wait till next year to go back..

Reviewed on Aug 22, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,123, price is now $964 per person
$964
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (33 reviews)
One of the cleanest places I’ve stay at loved it !

Reviewed on Aug 21, 2025

Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $736, price is now $633 per person
$633
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.8/10 Good! (385 reviews)
Average motel, staff very friendly

Reviewed on Aug 22, 2025

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Woolford Hotel Deals

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

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

Woolford
9.8/10 Exceptional! (57 reviews)
"As beautiful as the photos appear, they do NOT do this place justice! Just a beautiful place, incredibly peaceful, well-appointed and equipped for families, groups, or any type of rental. Loved our time here!"

Reviewed on Aug 12, 2025

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

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $283 total per night from Aug 25 to Aug 26
$283 total
Aug 25 - Aug 26
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Great stay at the Hyatt! Beautiful location and property, staff incredible! Only lost a star because drinks/food a bit overpriced and not 5 star."

Reviewed on Aug 18, 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
$135 nightly
The price is $150 total per night from Sep 1 to Sep 2
$150 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (876 reviews)
Amazing service and staff!
"Super comfortable bed! Haven’t sleep that well in a hotel for a while! The service and friendliness from all staff was AMAZING! Everyone was so kind. Our kids loved the pool as well. Wish we had a longer stay."

Reviewed on Aug 18, 2025

Solomons Inn Resort & Marina
See all 528 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.

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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 $595 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.