Title: Sherwood Vacation Packages 2026 from $397 | 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 $397 ## 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. ![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 $397 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included New York (NYC) 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 ![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 $1,156 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included New York (NYC) to Salisbury (SBY) 9.6/10 Exceptional! (369 reviews) Friendly and attentive staff, good cleaning services Reviewed on Oct 26, 2025 ![Beach Walk](https://images.trvl-media.com/lodging/91000000/90730000/90727900/90727853/f6dfd7c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beach Walk Downtown Ocean City $2,161 per person Apr 1 - Apr 5 found 2 hours ago Roundtrip non-stop flight included New York (NYC) to Salisbury (SBY) 7.6/10 Good! (95 reviews) Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing Reviewed on Oct 17, 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 $2,304 per person Apr 1 - Apr 5 found 2 hours ago Roundtrip non-stop flight included New York (NYC) 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 ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Kent Narrows & Marina $633 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included New York (NYC) to Salisbury (SBY) 9.4/10 Exceptional! (655 reviews) What a great place to stay. Staff is friendly. Property is clean. Rooms are spacious. Will definitely be back! Reviewed on Feb 15, 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/2026-03-26/2026-04-02/?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 27 - Feb 28 Total with taxes and fees 9.4/10 Exceptional! (370 reviews) Great! Reviewed on Feb 19, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=9323601&PinnedHotelID=9323601&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 $208 nightly $237 total Mar 6 - Mar 7 Total with taxes and fees 9/10 Wonderful! (1,890 reviews) The room really showed its age. The entire room was tilted.... so much so that a bottle rolled on the floor from the left to the right without any push. The bed was likewise tilted and really difficult to sleep comfortably. The elevator was out of order, and there were older guests on the 3rd floor ... Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F6%2F2026&endDate=3%2F7%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 $84 nightly $96 total Mar 3 - Mar 4 Total with taxes and fees 8.6/10 Excellent! (1,003 reviews) Yes Reviewed on Feb 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true®ionId=6034722) [See all 1,143 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F27%2F2026&endDate=2%2F28%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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