Title: Sherwood Vacation Packages 2026 from $340 | 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 $340 ## 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. ![Crystal Beach Hotel](https://images.trvl-media.com/lodging/5000000/4590000/4584500/4584433/c45fe589_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crystal Beach Hotel Downtown Ocean City $340 per person Apr 17 - Apr 20 found 19 hours ago Roundtrip flight included Philadelphia (PHL) to Salisbury (SBY) 8.2/10 Very Good! (1,333 reviews) Clean room, great service Reviewed on Dec 2, 2025 ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City $384 per person Apr 17 - Apr 20 found 19 hours ago Roundtrip flight included Philadelphia (PHL) to Salisbury (SBY) 9/10 Wonderful! (3,316 reviews) Really good and nice Reviewed on Feb 13, 2026 ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### St Michaels Inn $401 per person Apr 17 - Apr 20 found 19 hours ago Roundtrip flight included Philadelphia (PHL) to Salisbury (SBY) 8.2/10 Very Good! (1,003 reviews) Room was fine. Breakfast was poor with two empty hot breakfast servers. Rest of food substandard. Staff was nice Reviewed on Jan 18, 2026 ![Hyatt Place Ocean City / Oceanfront](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2557x3y4-d297081d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Ocean City / Oceanfront Downtown Ocean City $376 per person Apr 17 - Apr 20 found 19 hours ago Roundtrip flight included Philadelphia (PHL) to Salisbury (SBY) 9/10 Wonderful! (1,588 reviews) The staff were very courteous. The room was mostly clean (under the dresser was very dusty, and there was lots of trash), but otherwise the views were great, and the room was very comfortable. If I have the chance, I will return. Reviewed on Feb 3, 2026 ![Park Place Hotel](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/08f08113_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Place Hotel Downtown Ocean City $404 per person Apr 17 - Apr 20 found 19 hours ago Roundtrip flight included Philadelphia (PHL) to Salisbury (SBY) 9.2/10 Wonderful! (1,038 reviews) Staff was courteous and i had a great view of the ocean. Reviewed on Feb 8, 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/2026-03-14/2026-03-21/?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 ![Knapps Narrows Marina & Inn](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/6fde5623_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Knapps Narrows Marina & Inn 6176 Tilghman Island Road Tilghman MD Fully refundableReserve now, pay when you stay $90 nightly $99 total Feb 15 - Feb 16 Total with taxes and fees 9.4/10 Exceptional! (367 reviews) Always a great time. Reviewed on Jan 29, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=9323601&PinnedHotelID=9323601&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! (1,000 reviews) Staff-clean room Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true®ionId=6034722) ![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 $174 nightly $198 total Feb 22 - Feb 23 Total with taxes and fees 9/10 Wonderful! (1,886 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%2F22%2F2026&endDate=2%2F23%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=6034722) [See all 1,158 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F15%2F2026&endDate=2%2F16%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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