Woolford Holidays

Book a Hotel + Flight or Car together to unlock savings

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 5.455.692 ₫ per night from 28 Sept to 29 Sept
5.455.692 ₫
7.449.390 ₫ total
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (1,002 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 18 Aug 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 3.297.136 ₫ per night from 1 Sept to 2 Sept
3.297.136 ₫
3.660.058 ₫ total
1 Sept - 2 Sept
includes taxes & fees
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 15.062.454 ₫ per night from 17 Sept to 18 Sept
15.062.454 ₫
18.225.701 ₫ total
17 Sept - 18 Sept
includes taxes & fees
9.4/10 Exceptional! (361 reviews)
Lived up to its Reputation
"My wife and I recently stayed here to celebrate a milestone birthday. It certainly lived up to the hype and was one do the nicer places we have ever stayed."

Reviewed on 25 Aug 2025

Inn at Perry Cabin
See all 525 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.