Woolford Trips (flight + hotel)

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Top hotels in Woolford

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 P12,192 per night from Jul 22 to Jul 23
P12,192
P16,543 total
Jul 22 - Jul 23
includes taxes & 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
The price is P7,094 per night from Jul 6 to Jul 7
P7,094
P7,875 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (810 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
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is P6,905 per night from Jul 6 to Jul 7
P6,905
P7,595 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Older property but great experience"

Reviewed on Jun 25, 2025

St Michaels Inn
See all 514 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.