Sherwood Vacations from $566
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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.
The Latest Sherwood vacation packages
Price found within the past 48 hours. Click for updated prices.
Beach Walk
Downtown Ocean City
$1,616
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (107 reviews)
The property needs some TLC. And the beds we're re-made with the same sheets. Sheets we're dirty with spots on them. Im glad I brought my own blankets and
Reviewed on Aug 17, 2026
Majestic Hotel & Apartments
Downtown Ocean City
$1,707
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
6/10 (461 reviews)
“The hotel is way too expensive for what it offers. The furniture and facilities are old, there was an unpleasant smell in the room, and there wasn’t even a hair dryer. On top of that, they charged an additional $20 for parking. Overall, the quality and service were definitely not worth the price.”
Reviewed on Aug 17, 2026
Plim Plaza Hotel
Downtown Ocean City
$1,427
per person
Oct 2 - Oct 5
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.4/10 Good! (1,109 reviews)
Location is great, rooms are very small and dated , but other than that stay was great
Reviewed on Aug 17, 2026
Stay near popular Sherwood attractions
Back Creek Community Park
Back Creek Community Park is just one of the places to see in Sherwood, so why not enjoy the other things to explore during your travels? Wander the marina or discover the area's sunsets.
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.
Sherwood Hotel Deals
Knapps Narrows Marina & Inn
6176 Tilghman Island Road Sherwood MD
$150 nightly
$165 total
Aug 19 - Aug 20
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$98 nightly
$111 total
Aug 30 - Aug 31
Total with taxes and fees
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$132 nightly
$150 total
Aug 25 - Aug 26
Total with taxes and fees
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.
Find the Best Sherwood Vacation Packages
Sherwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | St. Michaels Winery, Bayside History Museum and Tilghman Watermen’s Museum |
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Frequently asked questions
How much does a Sherwood vacation package cost?
You can snap up a vacation package to this destination from $566 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?
November, December and January are great times to search for cheap Sherwood vacation packages. Opting to travel in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Sherwood?
Typically, a handful of days is enough to see the major attractions during your Sherwood vacation. However, if you'd like to have more time to relax or go on day trips, consider extending your trip.
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.
Does Expedia offer Book Now, Pay Later Sherwood vacation packages?
Secure your dream trip to Sherwood with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snap up travel deals while they last.
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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.
