Sherwood Vacations from $1,092
Book a Hotel + Flight or Car together to unlock savings
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.
Boardwalk One
Downtown Ocean City
$1,092
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
7.4/10 Good! (179 reviews)
The room was fresh cleaned, hot showers and plenty of space. Staff was very nice and informative. We were able to have covered parking. We watched the major storm with the high waves and wind from balcony but didn't disturb us with doors closed. Location was great for walking boardwalk. When too wet had an excellent tv and reception in the room.
Reviewed on Sep 28, 2026
Beach Walk
Downtown Ocean City
$2,426
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Salisbury (SBY)
7.6/10 Good! (126 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.
Reviewed on Oct 13, 2026
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.
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.
Sherwood Hotel Deals
Knapps Narrows Marina & Inn
6176 Tilghman Island Road Sherwood MD
Fully refundableReserve now, pay when you stay
$150 nightly
$165 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (399 reviews)
"The staff was extremely helpful and the view was amazing. I will definitely be returning."
Reviewed on Oct 15, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
$167 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"Clean room, very nice decor and great staff"
Reviewed on Oct 16, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$111 nightly
$126 total
Oct 20 - Oct 21
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 |
More vacations you might like
Frequently asked questions
How much does a Sherwood vacation package cost?
You can snap up a vacation package to this destination from $1,092 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.
Explore a world of travel with Expedia
- Washington Hotels
- All-Inclusive Resorts in Maryland
- Baltimore Hotels
- Easton Hotels
- Maryland Hotels
- Annapolis Hotels
- Cheap Hotels in Washington
- Inner Harbor Hotels
- Cambridge Hotels
- Tilghman Hotels
- National Harbor Hotels
- Hotels near Baltimore Washington Intl. Thurgood Marshall
- Cheap Hotels in Baltimore
- St. Michaels Hotels
- Cheap Hotels in Maryland
- Cabin Rentals in Maryland
- Oceanfront Hotels in Annapolis
- Chesapeake Beach Hotels
- Flights from Dallas (DFW) to Baltimore (BWI)
- Flights from Miami (MIA) to Baltimore (BWI)
- Flights from Baltimore Washington Intl. Thurgood Marshall
- Flights to Washington
- Flights to Baltimore
- Flights from Fort Lauderdale (FLL) to Baltimore (BWI)
- Flights from Los Angeles (LAX) to Baltimore (BWI)
- Flights from Boston (BOS) to Baltimore (BWI)
- Flights from Charlotte (CLT) to Baltimore (BWI)
- Flights from Atlanta (ATL) to Baltimore (BWI)
- Flights from New York (JFK) to Baltimore (BWI)
- Flights from Seattle (SEA) to Baltimore (BWI)
- Flights from San Francisco (SFO) to Baltimore (BWI)
- Flights from Denver (DEN) to Baltimore (BWI)
- Flights from Phoenix (PHX) to Baltimore (BWI)
- Flights from Tampa (TPA) to Baltimore (BWI)
- Flights from Chicago (ORD) to Baltimore (BWI)
- Flights to Maryland
- Flights from Orlando (MCO) to Baltimore (BWI)
- Flights from Houston (IAH) to Baltimore (BWI)
- Flights from Detroit (DTW) to Baltimore (BWI)
- Flights to Annapolis
- Flights from Minneapolis (MSP) to Baltimore (BWI)
- Captain Avery Museum
- Washington Vacations
- Chesapeake Beach Vacations
- St. Michaels Winery
- Maryland Women's Heritage Center
- Eubie Blake National Jazz Institute and Cultural Center
- Baltimore City Hall
- Easton Vacations
- National Aquarium in Baltimore
- Ego Alley
- Visit Maryland
- Hopkins Plaza
- Uss Constellation
- Baltimore Convention Center
- Robert Long House
- Phillips Wharf Environmental Center
- Chesapeake Beach Railway Museum
- Sandy Point State Park
- Charm'tastic Mile
- Under Sky One Family Sculpture
- Shadyside Park
- Talbot County Visitor Center
- Uscg Lightship Chesapeake
- Oriole Park at Camden Yards
- Academy Art Museum
- North Beach Vacations
- Visit Annapolis
- Chesapeake Bay Bridge
- St. Mary's Spiritual Center and Historic Site
- Visit Washington
- National Historic Seaport of Baltimore
- Chesapeake Beach Water Park
- Maryland Vacations
- Talbot Massage
- The Phoenix Shot Tower
- U.s. Naval Academy
- Breezy Point Beach
- Bozman Vacations
- University of Maryland Medical Center
- Harriet Tubman Underground Railroad National Historical Park
- St. Michaels Vacations
- Baltimore Maritime Museum
- Pickering Creek Audubon Center
- The Third Haven Friends Meeting House
- Chesapeake Bay Environmental Center
- Baltimore American Indian Center
- Holocaust Memorial
- Kunta Kinte–Alex Haley Memorial
- Rod n Reel Charter Fishing
- Federal Hill Vacations
- Visit North Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.