Sherwood Vacations from $749
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
$2,262
per person
Nov 26 - Nov 30
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
7.8/10 Good! (115 reviews)
The room was clean and comfortable. The staff were pleasant. Parking was an issue, but may have been due to bike week was going on. Good location.
Reviewed on Sep 13, 2026
The Shore House
West Ocean City
$2,132
per person
Nov 26 - Nov 30
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Salisbury (SBY)
6.6/10 (782 reviews)
Ants in the room, spiderwebs, insects, and old dirt in the stairways, TVs didn't work in the rooms- most channels didn't have subscriptions.. Check-in desk and Continental breakfast was at another hotel on the property. Beds were comfortable.
Reviewed on Sep 15, 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
Fully refundableReserve now, pay when you stay
$150 nightly
$165 total
Sep 20 - Sep 21
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$83 nightly
$95 total
Sep 20 - Sep 21
Total with taxes and fees
8.8/10 Excellent! (1,183 reviews)
"Great hotel, close to downtown, and in a nice area! Great staff!!!"
Reviewed on Sep 17, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$148 nightly
$169 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,997 reviews)
"Very impressed with the staff and all the help they provided for us.....! Cleanliness tops. My only complaint is with the cable TV quality. Very poor picture quality and cumbersome remote. This certainly requires a big upgrade. Also it wasn`t till the second day that I found electric outlets for ..."
Reviewed on Sep 16, 2026
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 $749 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
- Wyndham Hotels in St. Michaels
- Bedandbreakfast in St. Michaels
- Hotels in Sherwood
- Pet Friendly in St. Michaels
- Ocean View in St. Michaels
- Hotels in Tilghman
- Inns in Romancoke
- Marriott Hotels & Resorts Hotels in St. Michaels
- Hotels in Oxford
- 4 Star Hotels in St. Michaels
- Privatevacationhomes in St. Michaels
- Hotels in St. Michaels
- 5 Star Hotels in St. Michaels
- Hotels in North Beach
- JetBlue Airways Boston (BOS) to Baltimore (BWI) flights
- Flights to Eastern Shore
- Delta Air Lines Atlanta (ATL) to Baltimore (BWI) flights
- Flights to Tilghman
- Flights to Annapolis
- Flights to Kent Island
- Flights from San José (SJO) to Easton (ESN)
- Oceanic Airlines West Harrison (HPN) to Easton (ESN) flights
- Flights to Easton
- Flights from Jamaica (JFK) to Easton (ESN)
- Flights to St. Michaels
- Ego Alley
- Visit Easton
- Eastern Shore All Inclusive Vacation Packages
- Queenstown Vacations
- Visit Eastern Shore
- Waldorf Vacations
- Chesapeake Beach Vacations
- Chesapeake Beach Water Park
- Where to stay in North Beach
- Kent Island All Inclusive Vacation Packages
- Where to stay in Washington
- Baltimore Vacations
- Kent Island All Inclusive Vacation Packages
- Visit St. Michaels
- Kent Island All Inclusive Vacation Packages
- Where to stay in Chesapeake Beach
- Washington Vacations
- Kent Island All Inclusive Vacation Packages
- Visit Annapolis
- St. Michaels Vacations
- Where to stay in Annapolis
- Mount Rainier Vacations
- Visit Cambridge
- Visit Deale
- Where to stay in Eastern Shore
- Inner Harbor Vacations
- Chesapeake Bay Bridge
- Where to stay in Cambridge
- Visit Chesapeake Beach
- Visit Tilghman
- Eastern Shore All Inclusive Vacation Packages
- Kent Island All Inclusive Vacation Packages
- Breezy Point Beach
- Eastern Shore All Inclusive Vacation Packages
- Eastern Shore All Inclusive Vacation Packages
- North Beach Vacations
- Kent Island All Inclusive Vacation Packages
- Where to stay in Baltimore
- Visit Kent Island
- Where to stay in Stevensville
- Annapolis Vacations
- Visit North Beach
- Visit Rose Haven
- Where to stay in Kent Island
- Easton Vacations
- Where to stay in National Harbor
- Pickup Car Rentals in Easton
- Convertible Car Rentals in Annapolis
- Hertz Rental Cars in St. Michaels
- Car rentals in Chesapeake Beach
- Car rentals in North Beach
- Car rentals in Easton
- Car rentals in St. Michaels
- Van Car Rentals in Easton
- Car rentals in Deale
- Enterprise Rental Cars in St. Michaels
- Car rentals in Oxford
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
