Title: Sherwood Vacation Packages 2026 from $788 | 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 $788 ## 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. ![Paradise Plaza Inn](https://images.trvl-media.com/lodging/1000000/130000/120600/120559/6bc5da90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Paradise Plaza Inn Downtown Ocean City $788 per person Apr 1 - Apr 4 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Salisbury (SBY) 7.6/10 Good! (1,001 reviews) Checked the in for the ice skating, pool and hot tub. There was a cheerleading conference going on that weekend, so we decided we would wait and use those Sunday when it emptied out. On Sunday they closed the pool and hot tub early, around 8pm. Those are not open Monday through Wednesday either. Don’t stay here during the week in the winter. Reviewed on Dec 30, 2025 ![Boardwalk One](https://images.trvl-media.com/lodging/3000000/2060000/2053600/2053558/73b85086_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boardwalk One Downtown Ocean City $850 per person Apr 1 - Apr 4 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Salisbury (SBY) 7.4/10 Good! (170 reviews) Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo. Reviewed on Oct 1, 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 $902 per person Apr 1 - Apr 4 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Salisbury (SBY) 9/10 Wonderful! (3,316 reviews) The only place we stay when we go to Ocean City. Great location, plenty of parking, friendly staff, good food, 2 arcade areas! On the boardwalk, far enough from the inlet crowds, but a nice walk. Great beach location & views. Reviewed on Feb 1, 2026 ![Quality Inn Oceanfront](https://images.trvl-media.com/lodging/1000000/20000/13300/13212/17228a7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Inn Oceanfront Midtown Ocean City $868 per person Apr 1 - Apr 4 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Salisbury (SBY) 8.2/10 Very Good! (1,478 reviews) I’ve stayed here a few times and I’ve never had an issue. Very nice staff and clean rooms. Reviewed on Nov 2, 2025 ![Quality Inn Boardwalk](https://images.trvl-media.com/lodging/1000000/20000/13300/13231/bba7d0ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Inn Boardwalk Downtown Ocean City $882 per person Apr 1 - Apr 4 found 1 day ago Roundtrip non-stop flight included New York (NYC) to Salisbury (SBY) 8.2/10 Very Good! (1,002 reviews) I am so pleased with everything at this hotel from the staff to my room the girl at the front desk I think maybe her name was Keisha she was wonderful I will definitely be choosing this hotel for future vacations Reviewed on Oct 20, 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/2026-03-08/2026-03-15/?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) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Graduate by Hilton Annapolis 126 West St Annapolis MD Fully refundableReserve now, pay when you stay $159 nightly $181 total Feb 23 - Feb 24 Total with taxes and fees 9.2/10 Wonderful! (1,004 reviews) The room was very spacious. Staff were nice. Amenities were excellent. Good location for our stay. Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true®ionId=6034722) ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Chesapeake Bay 100 Heron Blvd Cambridge MD Fully refundableReserve now, pay when you stay $211 nightly $240 total Feb 12 - Feb 13 Total with taxes and fees 8.6/10 Excellent! (1,001 reviews) Nice stay, but a little too crowded. Reviewed on Jan 30, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=890486&PinnedHotelID=890486&HadPinnedHotel=true®ionId=6034722) [See all 1,158 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F9%2F2026&endDate=2%2F10%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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