Woolford Vacations

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    Save up to ￥45,448 when you book a flight and hotel together*
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Find the Best Woolford Vacation Packages

Woolford Hotel Deals

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 ￥30,498 per night from Aug 25 to Aug 26
￥30,498
￥41,636 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"#1 family get away. Kids absolutely love the pool."

Reviewed on Aug 14, 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
The price is ￥21,063 per night from Sep 1 to Sep 2
￥21,063
￥23,381 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (867 reviews)
"The hotel was newly renovated and the rooms were very nice and beds very comfortable. The pool was amazing and the staff was very friendly and helpful. Will be back."

Reviewed on Aug 12, 2025

Solomons Inn Resort & Marina
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is ￥14,657 per night from Sep 3 to Sep 4
￥14,657
￥16,122 total
Sep 3 - Sep 4
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Very nice stay"

Reviewed on Aug 13, 2025

St Michaels Inn
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.

Frequently asked questions

How much does a Woolford vacation package cost?
You can pick up a vacation package to this popular destination 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?
Plan your getaway for the off-season and you're likely to score cheap Woolford vacation packages. Remember that school vacation periods and local festivals and events can impact prices, so do a little research before you go.
How many days is enough for Woolford?
The ideal length for your Woolford vacation depends on what you'd like to do. Typically, a few days to a week will give you enough time to go to all the top attractions and discover some hidden gems along the way.
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.
How to plan a trip to Woolford?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Woolford.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your accommodations will probably be the biggest expense during your trip to Woolford.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to experience in Woolford. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Woolford vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.