Sherwood Vacation Packages
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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.
Top Sherwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boardwalk One
Downtown Ocean City
CA $1,149
per person
Nov 8 - Nov 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.4/10 Good! (174 reviews)
The house keeper/maneger was mean and inconsiderate. On my last day of stay I asked for clean towels since we have been using the same towels all thought out I want clean towel and the house keeper told me flat out no because the towels are for her incoming guests.
Reviewed on Aug 24, 2026
Miramar Condominiums
Downtown Ocean City
CA $2,136
per person
Nov 8 - Nov 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9.4/10 Exceptional! (26 reviews)
Very convenient location, helpful staff. The unit itself (#504) could use some updating. The carpeting is loose/has big wrinkles in it and the living room furniture is not very comfortable. The mattress in the sofa sleeper is well past its prime. There was a foam topper on it which helped a little, but it’s not very comfortable. The king mattress is also in need of replacement. Overall, the condo fit our needs very well for our ocean city stay. Please note that there are very limited supplies at the condo (paper towel, shampoo, etc), so plan to bring shampoo, condition, something to clean the kitchen counters with, etc. if you plan to use the dishwasher more than twice or the washer more than twice you will need to bring detergent.
Reviewed on Aug 19, 2026
Ready to book your vacation to Sherwood?
Sherwood Hotel Deals
Knapps Narrows Marina & Inn
6176 Tilghman Island Road Sherwood MD
CA $206
CA $227 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (396 reviews)
"We enjoyed the peaceful garden and view from the balcony. The pool was great…we had it to ourselves late afternoon. The continental breakfast was very nice."
Reviewed on Aug 19, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $134
CA $153 total
Aug 30 - Aug 31
includes taxes & fees
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
CA $126
CA $191 total
Aug 30 - Aug 31
includes taxes & 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.
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.
Frequently asked questions
How much does a Sherwood vacation package cost?
You'll find cheap prices from CA $1,149 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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
