Woolford Vacations

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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 ₩286,678 per night from Aug 26 to Aug 27
₩286,678
₩391,376 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (1,001 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
The price is ₩173,086 per night from Aug 31 to Sep 1
₩173,086
₩192,138 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (880 reviews)
Great experience at the hotel.
"We had a great experience at the hotel. The pool and the lifeguards were amazing, having early free breakfast was extremely helpful with a child, and generally, the hotel fuel was very good and local."

Reviewed on Aug 23, 2025

Solomons Inn Resort & Marina
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is ₩790,716 per night from Sep 17 to Sep 18
₩790,716
₩956,774 total
Sep 17 - Sep 18
includes taxes & fees
9.4/10 Exceptional! (360 reviews)
"IPC is a "hidden gem." It was great, from "soup to nuts." Especially the staff, who were all friendly, polite, knowledgeable, flexible, and helpful. Thanks to all of them on our behalf, please: staff are what make all the difference at any resort. (SPA treatments are a must.) Just one suggestion: ..."

Reviewed on Aug 14, 2025

Inn at Perry Cabin
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.

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.