Title: Sherwood Vacation Packages 2026 from $973 | 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 $973 ## 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. ![Americana Condos 10th street](https://images.trvl-media.com/lodging/65000000/64560000/64555700/64555604/105643e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Americana Condos 10th street Downtown Ocean City $973 per person Apr 3 - Apr 6 found 5 hours ago Roundtrip non-stop flight included Cleveland (CLE) to Salisbury (SBY) 8.4/10 Very Good! (19 reviews) straight fire, definitely going back Reviewed on Jun 21, 2025 ![The Shore House](https://images.trvl-media.com/lodging/4000000/3750000/3743000/3742941/cdb4342b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shore House West Ocean City $1,717 per person Apr 3 - Apr 6 found 5 hours ago Roundtrip non-stop flight included Cleveland (CLE) to Salisbury (SBY) 6.8/10 (598 reviews) Overall it was perfect for country calling. There’s a shuttle at the hotel next door that we took everyday down to the entrance for $5 cash. The beds were comfortable, clean and the shower water was hot. I almost ended up cancelling though because during the off season it is nearly impossible to reach the hotel!! I called probably 10 times and couldn’t get an answer on my booking until Expedia themselves contacted me about changing the days we were staying. While the location was great, convenient and good for the price for country calling, the lack of communication was just shocking. As someone who travels often this customer service really needs to improve or I think sales will really suffer. Reviewed on Oct 5, 2025 ![Surf Villa Apartments](https://images.trvl-media.com/lodging/91000000/90620000/90612400/90612343/5e121fab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Surf Villa Apartments Midtown Ocean City $1,513 per person Mar 25 - Mar 29 found 1 day ago Roundtrip non-stop flight included Denver (DEN) to Salisbury (SBY) 9.4/10 Exceptional! (3 reviews) ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn at Perry Cabin Downtown St. Michaels Save 100% on your flight $2,015 per person Apr 6 - Apr 11 found 1 day ago Roundtrip flight included New York (JFK) to Salisbury (SBY) 9.6/10 Exceptional! (369 reviews) Friendly and attentive staff, good cleaning services Reviewed on Oct 26, 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 $1,139 per person Apr 3 - Apr 6 found 5 hours ago Roundtrip non-stop flight included Cleveland (CLE) 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 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/2026-03-12/2026-03-19/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ESN&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6034722) ## 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! (1,886 reviews) THis is the second time in a row staying here bith times they placed my room on the court yard while I had to listen to loud music form a wedding being heald to late in the evening. AAlso both times our room was not cleaned with new towls etc. When I noticed after 5:00 PM the hotel just asid sorry ... Reviewed on Feb 9, 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 Fully refundableReserve now, pay when you stay $83 nightly $94 total Feb 22 - Feb 23 Total with taxes and fees 8.6/10 Excellent! (1,001 reviews) The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. Reviewed on Feb 11, 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 $82 nightly $93 total Mar 8 - Mar 9 Total with taxes and fees 8.8/10 Excellent! (988 reviews) Water would not get hot. Other than that it was perfect. Z Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=2982&PinnedHotelID=2982&HadPinnedHotel=true®ionId=6034722) [See all 1,156 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F13%2F2026&endDate=2%2F14%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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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Sherwood vacation package cost? ### What are the cheapest months to go to Sherwood? ### How many days is enough for Sherwood? ### How to find the best Sherwood package deals? ### Is it cheaper to book a Sherwood vacation as a package? ### When to book a vacation package to Sherwood? ### Does Expedia offer Book Now, Pay Later Sherwood vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Wittman Hotels ](https://www.expedia.com/Wittman-Hotels.d3000440946.Travel-Guide-Hotels) - [Cottages in Wittman 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