Title: Sherwood Vacation Packages 2026 from $640 | Expedia.com [Sherwood Travel Guide](https://expedia.com/Sherwood.dx6034722)[Hotels in Sherwood](https://expedia.com/Sherwood-Hotels.d6034722.Travel-Guide-Hotels)[Vacation Rentals in Sherwood](https://expedia.com/Sherwood-Vacation-Rentals.d6034722.Travel-Guide-VacationRentals)[Flights to Sherwood](https://expedia.com/Cheap-Flights-To-Sherwood.d6034722.Travel-Guide-Flights)[Car Rentals in Sherwood](https://expedia.com/Car-Rentals-In-Sherwood.d6034722.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6034722/0bcbb682-8042-4738-8664-a432e128f170.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Sherwood Vacations from $640 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, 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](https://www.expedia.com/St-Michaels-Winery-St-Michaels.d553248633992438808.Vacation-Attraction), [Chesapeake Bay Maritime Museum](https://www.expedia.com/Chesapeake-Bay-Maritime-Museum-St-Michaels.d553248633992441010.Vacation-Attraction) and [Tilghman Watermen’s Museum](https://www.expedia.com/Tilghman-Watermens-Museum-Tilghman.d553248621555566156.Vacation-Attraction). 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. ![Ashore Resort & Beach Club](https://images.trvl-media.com/lodging/1000000/30000/20400/20346/e36f7efc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ashore Resort & Beach Club North Ocean City $640 per person Apr 12 - Apr 16 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 8.2/10 Very Good! (1,825 reviews) Clean, comfortable and quiet. Reviewed on Dec 28, 2025 ![Miramar Condominiums](https://images.trvl-media.com/lodging/91000000/90310000/90308700/90308605/f837bfd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miramar Condominiums Downtown Ocean City $1,275 per person Apr 12 - Apr 16 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 9.4/10 Exceptional! (15 reviews) Stayed in unit 505 and it was beautiful! We loved it! Reviewed on Aug 23, 2025 ![Americana Motor Inn](https://images.trvl-media.com/lodging/19000000/18140000/18132800/18132755/4e1c1d86_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Americana Motor Inn Downtown Ocean City $2,915 per person Mar 29 - Apr 3 found 7 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Salisbury (SBY) 8.4/10 Very Good! (883 reviews) Rooms were clean, best location and very reasonable price. Reviewed on Oct 22, 2025 ![Sahara Motel](https://images.trvl-media.com/lodging/91000000/90730000/90727700/90727609/e06e1213_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sahara Motel Downtown Ocean City $768 per person Apr 30 - May 3 found 9 hours ago Roundtrip non-stop flight included Chicago (CHI) to Salisbury (SBY) 7.6/10 Good! (516 reviews) I was very happy with our room - loved being on the first floor. I plan to return next time I come to the beach. Reviewed on Oct 31, 2025 ![Bethany Beach Ocean Suites Residence Inn by Marriott](https://images.trvl-media.com/lodging/11000000/10920000/10912400/10912388/f4da198d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bethany Beach Ocean Suites Residence Inn by Marriott Downtown Bethany Beach $835 per person Apr 16 - Apr 19 found 9 hours ago Roundtrip non-stop flight included Chicago (CHI) to Salisbury (SBY) 9/10 Wonderful! (770 reviews) Super helpful staff, breakfast was amazing Reviewed on Jan 28, 2026 Don't see what you're looking for? See all available trips from Columbus to Sherwood [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-10/2026-03-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ESN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Sherwood Hotel Deals ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD Fully refundableReserve now, pay when you stay $229 nightly $261 total Feb 26 - Feb 27 Total with taxes and fees 9/10 Wonderful! (1,884 reviews) Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back! Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=6034722) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court Annapolis MD $83 nightly $94 total Feb 22 - Feb 23 Total with taxes and fees 8.6/10 Excellent! (1,001 reviews) Room was spotless. Staff was very courteous. Would highly recommended. Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true®ionId=6034722) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta ES Suites Annapolis 170 Admiral Cochrane Dr Edgewater MD Fully refundableReserve now, pay when you stay $88 nightly $101 total Mar 12 - Mar 13 Total with taxes and fees 8.8/10 Excellent! (985 reviews) We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️ Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=2982&PinnedHotelID=2982&HadPinnedHotel=true®ionId=6034722) [See all 1,158 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F11%2F2026&endDate=2%2F12%2F2026®ionId=6034722) 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](https://www.expedia.com/St-Michaels-Winery-St-Michaels.d553248633992438808.Vacation-Attraction), [Bayside History Museum](https://www.expedia.com/Bayside-History-Museum-North-Beach.d553248621554160436.Vacation-Attraction) and [Tilghman Watermen’s Museum](https://www.expedia.com/Tilghman-Watermens-Museum-Tilghman.d553248621555566156.Vacation-Attraction) 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