Title: Sherwood Vacation Packages 2026 from $761 | 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 $761 ## 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. ![Hotel Monte Carlo Ocean City](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/8bf1c888_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Monte Carlo Ocean City Downtown Ocean City $761 per person Apr 11 - Apr 18 found 9 hours ago Roundtrip non-stop flight included Boston (BOS) to Salisbury (SBY) 7.8/10 Good! (1,004 reviews) It was very comfortable and spacious room Reviewed on Nov 4, 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 Save 100% on your flight $3,224 per person Apr 11 - Apr 18 found 9 hours ago Roundtrip non-stop flight included Boston (BOS) 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 ![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 $822 per person Apr 11 - Apr 18 found 9 hours ago Roundtrip non-stop flight included Boston (BOS) 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 ![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 $1,275 per person Apr 12 - Apr 16 found 4 hours ago Roundtrip non-stop flight included Pittsburgh (PIT) 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 ![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 $975 per person Apr 24 - May 1 found 1 day ago Roundtrip non-stop flight included Tampa (TPA) 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/2026-03-09/2026-03-16/?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) ![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) Room was spotless. Staff was very courteous. Would highly recommended. Reviewed on Feb 5, 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 $91 nightly $104 total Mar 1 - Mar 2 Total with taxes and fees 8.8/10 Excellent! (984 reviews) We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️ Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=2982&PinnedHotelID=2982&HadPinnedHotel=true®ionId=6034722) [See all 1,158 properties in Sherwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F10%2F2026&endDate=2%2F11%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 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