Sherwood Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Sherwood Vacation

When you organize a vacation package to Sherwood, you can relax and enjoy your getaway knowing that all your travel arrangements have been made in advance. Discover the charms of this vibrant city while based in a neighborhood like Deale Beach, which is good for walking. A trip to Sherwood is an excellent opportunity to take in the sights. Check out renowned attractions like St. Michaels Winery, Chesapeake Bay Maritime Museum and Tilghman Watermen’s Museum. Whoever you're escaping with and whatever your bank balance, your dream Sherwood vacation is only clicks away with Expedia.

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Sherwood Hotel Deals

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road Sherwood MD
The price is CA $213 per night from Jul 9 to Jul 10
CA $213
CA $234 total
Jul 9 - Jul 10
includes taxes & fees
9.4/10 Exceptional! (388 reviews)
"Great place!"

Reviewed on Jun 25, 2026

Knapps Narrows Marina & Inn
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is CA $128 per night from Jul 19 to Jul 20
CA $128
CA $195 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,887 reviews)
"Other than the very comfortable beds, the best thing about our stay here is the location. It's an easy 10 minutes walk to the wharf, market space, USNA, state capital, etc. The rooms were very clean and the valet staff was super fast."

Reviewed on Jul 8, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 12 to Jul 13
CA $147
CA $167 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,028 reviews)
"We had an average stay. The hotel itself is a bit dated - needs renovation and updates. Our room had an odor - like mildew. The front desk staff is underwhelming. Lacked energy and friendliness and didn't want to be bothered honestly. However, the wait staff at breakfast in the restaurant were great. ..."

Reviewed on Jul 8, 2026

DoubleTree by Hilton Hotel Annapolis
See all 1,171 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.
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Stay near popular Sherwood attractions

Goat Island

Commune with nature and explore the great outdoors at Goat Island during your travels in Sherwood. Wander the marina or discover the area's sunsets.
See properties

Frequently asked questions

How much does a Sherwood vacation package cost?
You'll find cheap prices on Expedia for your Sherwood getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Sherwood costs.
What are the cheapest months to go to Sherwood?
Plan your trip for the shoulder or low season and you're likely to get cheap Sherwood vacation packages. Keep in mind that school vacation periods and major local events can impact prices, so do some research before booking.
How many days is enough for Sherwood?
Typically, a handful of days is enough to see the top sights during your Sherwood vacation. But if you prefer to have some time to chill out or take day trips, consider extending your itinerary.
How to find the best Sherwood package deals?
Start your search for a Sherwood package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Sherwood package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sherwood escape off to a flying start.
Is it cheaper to book a Sherwood vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Sherwood vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Sherwood?
Secure incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Sherwood getaway.
How to plan a trip to Sherwood?

  1. Choose when to travel: Check your calendar and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to visit Sherwood.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Sherwood.
  3. Work out your trip length: Consider how long you'd like to spend discovering Sherwood. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Sherwood vacation package that brings all your bookings together.

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