Sherwood Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Sherwood Vacation Packages

Sherwood Hotel Deals

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,783 reviews)
"Wonderful stay!"

Reviewed on Jun 27, 2025

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Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩139,482 per night from Jul 21 to Jul 22
₩139,482
₩159,009 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"It was very nice and comfortable"

Reviewed on Jun 22, 2025

Hilton Garden Inn Annapolis Downtown
Best Western Annapolis
Best Western Annapolis
2.5 out of 5
2520 Riva Rd, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩116,385 per night from Jul 27 to Jul 28
₩116,385
₩132,679 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"good"

Reviewed on Jun 22, 2025

Best Western Annapolis
See all 1,176 properties in Sherwood
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 Sherwood vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation to Sherwood costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Sherwood?
To pick up cheap Sherwood vacation packages, plan your getaway outside of busy periods like public holidays and major events. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Sherwood?
Usually, a handful of days is enough to visit the major attractions during your Sherwood vacation. But if you want to have more time to kick back or take day tours, think about extending your itinerary.
How to find the best Sherwood package deals?
Finding a cheap Sherwood package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Sherwood package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Sherwood vacation as a package?
You can enjoy significant savings on your Sherwood break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Sherwood?
If you have your Sherwood vacation dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Sherwood?

  1. Pick your dates: The things you want to do in Sherwood and your favorite season will help you decide when to go.
  2. Set your budget: Factor in costs like flights, meals and transportation when calculating how much to put aside for your trip to Sherwood. Then, pick a hotel that matches your budget, whether that's a low-cost option or a more luxurious retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Sherwood. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the right Sherwood vacation package for you.

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