Woolford Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Woolford

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 ฿5,835 per night from 6 Aug to 7 Aug
฿5,835
฿6,477 total
6 Aug - 7 Aug
includes taxes & fees
7.8/10 Good! (845 reviews)
"Awesome Huge and Clean Pool!"

Reviewed on 28 Jul 2025

Solomons Inn Resort & Marina
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 ฿6,774 per night from 25 Aug to 26 Aug
฿6,774
฿9,250 total
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"My issue was with the bedding, it was not very comfortable"

Reviewed on 24 Jul 2025

Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is ฿19,986 per night from 28 Aug to 29 Aug
฿19,986
฿24,184 total
28 Aug - 29 Aug
includes taxes & fees
9.4/10 Exceptional! (355 reviews)
"The setting is spectacular and the staff could not have been kinder and more helpful."

Reviewed on 13 Jul 2025

Inn at Perry Cabin
See all 521 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 holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. But how much your holiday 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 holiday packages. Remember that school holiday 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Woolford holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and accommodation 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 holiday 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 holiday.
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 accommodation 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 holiday package.

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