Title: Sherwood Vacation Packages 2026 from $622 | 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 $622 ## 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. ![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 $622 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) 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 ![The Americana Hotel](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279694/fc3af3e9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Americana Hotel Downtown Ocean City $677 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 8.6/10 Excellent! (1,118 reviews) Our room was ok. Hotel is in need of remodel. No ice machines on our floor. Had to go to the first floor to get ice. Heat pump in our room was very loud and woke us every time it came on. The place was not necessarily dirty but old and it shows. The staff were wonderful and very helpful. Reviewed on Feb 21, 2026 ![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 $778 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 9/10 Wonderful! (3,316 reviews) Great view of ocean from the balcony. Reviewed on Feb 26, 2026 ![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 $629 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 8.4/10 Very Good! (883 reviews) Rooms were clean, best location and very reasonable price. Reviewed on Oct 22, 2025 ![Ocean 1 Hotel and Suites](https://images.trvl-media.com/lodging/9000000/8020000/8013600/8013501/c6ebe75b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean 1 Hotel and Suites Downtown Ocean City $732 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 8.2/10 Very Good! (695 reviews) Pros: The hotel itself was fine, with great staff who were friendly and accommodating. Cons: Parking leaves much to be desired. Spaces are extremely limited, and if you do manage to find one, they’re very tight. My bigger issue, though, was the construction directly in front of the hotel. While I understand this isn’t the hotel’s fault, it significantly impacted the overall experience. During the day, large equipment was constantly in use, and at night, huge generators ran nonstop. The noise was so overwhelming that you couldn’t even hear the ocean. On top of that, the construction obstructed the views—rather than looking out at the water, you were staring at metal structures the entire time. Any construction needs to be disclosed to customers prior to booking any accommodations. Reviewed on Nov 29, 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/2026-03-28/2026-04-04/?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 $100 nightly $110 total Mar 1 - Mar 2 Total with taxes and fees 9.4/10 Exceptional! (370 reviews) Great! Reviewed on Feb 19, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%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! (1,877 reviews) Such a cool place to stay! Water pressure wasn’t great but it’s a very old building. Reviewed on Feb 26, 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! (1,006 reviews) The staff was very helpful. The room was nice and there were shops & restaurants nearby. Reviewed on Feb 27, 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=3%2F1%2F2026&endDate=3%2F2%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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