Title: Sherwood Holidays 2025 | Expedia.co.uk [Hotels in Sherwood](https://expedia.co.uk/Sherwood-Hotels.d6034722.Travel-Guide-Hotels)[Holiday Rentals in Sherwood](https://expedia.co.uk/Sherwood-Holiday-Rentals.d6034722.Travel-Guide-HolidayRentals)[Sherwood Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Sherwood.d6034722.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Sherwood Holidays ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected #### Your Sherwood Holiday When you organise a holiday 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 neighbourhood 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.co.uk/St-Michaels-Winery-St-Michaels.d553248633992438808.Attraction), [Chesapeake Bay Maritime Museum](https://www.expedia.co.uk/Chesapeake-Bay-Maritime-Museum-St-Michaels.d553248633992441010.Attraction) and [Tilghman Watermen’s Museum](https://www.expedia.co.uk/Tilghman-Watermens-Museum-Tilghman.d553248621555566156.Attraction). Whoever you're escaping with and whatever your bank balance, your dream Sherwood holiday is only clicks away with Expedia. ## Sherwood Essential Information | Language | English | | --- | --- | | Currency | U.S dollars | | Max Temp Winter | 7ºC | | Max Temp Summer | 27ºC | | Top Sights | [St. Michaels Winery](https://www.expedia.co.uk/St-Michaels-Winery-St-Michaels.d553248633992438808.Attraction), [Bayside History Museum](https://www.expedia.co.uk/Bayside-History-Museum-North-Beach.d553248621554160436.Attraction) and [Oxford Museum](https://www.expedia.co.uk/Oxford-Museum-Oxford.d553248621532662338.Attraction) | ## Top hotels in Sherwood ![Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/a8374ca7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND Sherwood, MD 10/10 Exceptional! (37 reviews) What a spectacular home!! We all loved our stay and took advantage of the beautiful heated pool, dock, fire pit and playground. In the evening the pool table, ping pong and foosball were enjoyed by all. Stunning views, beautiful furnishings and comfortable bedding. Hopefully we will have occasion ... Reviewed on 20 Oct 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=64567851&PinnedHotelID=64567851&HadPinnedHotel=true®ionId=6034722) [](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=64567851&PinnedHotelID=64567851&HadPinnedHotel=true®ionId=6034722) ![6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/caba515d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access Sherwood, MD 9.8/10 Exceptional! (19 reviews) We didn't use the pool - it was too cold for it in October Reviewed on 21 Oct 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=92607228&PinnedHotelID=92607228&HadPinnedHotel=true®ionId=6034722) [](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=92607228&PinnedHotelID=92607228&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 8.8/10 Excellent! (1,881 reviews) It was a clean room Reviewed on 8 Nov 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=6034722) [](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=6034722) [See all 1,168 properties in Sherwood](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F11%2F2025&endDate=12%2F11%2F2025®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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes ### Accommodation - [2 Star Hotels in Kent Island](https://www.expedia.co.uk/2Star-Kent-Island-Hotels.s20-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Kent Island](https://www.expedia.co.uk/5Star-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Royal Oak](https://www.expedia.co.uk/5Star-Royal-Oak-Hotels.s50-0-d6047042.Travel-Guide-Filter-Hotels) - [Bozman Hotels](https://www.expedia.co.uk/Bozman-Hotels.d3000440434.Travel-Guide-Hotels) - [Chesapeake Beach Hotels](https://www.expedia.co.uk/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels) - [Churchton Hotels](https://www.expedia.co.uk/Churchton-Hotels.d6247936.Travel-Guide-Hotels) - [Deale Beach Hotels](https://www.expedia.co.uk/Deale-Beach-Hotels.d553248635975876712.Travel-Guide-Hotels) - [Deale Hotels](https://www.expedia.co.uk/Deale-Hotels.d55664.Travel-Guide-Hotels) - [Farmstay in Kent Island](https://www.expedia.co.uk/Kent-Island-Agritourism.d553248635077608788-aaAgritourism.Travel-Guide-Accommodation) - 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[Hotels with Gym in Kent Island](https://www.expedia.co.uk/Kent-Island-Hotels-Hotel-With-Gym.0-0-d553248635077608788-thotelwithgym.Travel-Guide-Filter-Hotels) - [Hotels with Pool in Kent Island](https://www.expedia.co.uk/Kent-Island-Hotels-Hotels-With-Pool.0-0-d553248635077608788-tHotelswithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Kent Island](https://www.expedia.co.uk/Kent-Island-Hotels-Luxury-Hotel.0-0-d553248635077608788-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Kent Island](https://www.expedia.co.uk/Kent-Island-Hotels-Pet-Friendly-Hotel.0-0-d553248635077608788-tPetFriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Kent Island](https://www.expedia.co.uk/Kent-Island-Hotels-Spa-Hotels.0-0-d553248635077608788-tSpaHotels.Travel-Guide-Filter-Hotels) - [Kent Island Hotels](https://www.expedia.co.uk/Kent-Island-Hotels.d553248635077608788.Travel-Guide-Hotels) - [Houseboats in Kent Island](https://www.expedia.co.uk/Kent-Island-Houseboats.d553248635077608788-aaHouseboats.Travel-Guide-Accommodation) - [Lodges in Kent Island](https://www.expedia.co.uk/Kent-Island-Lodges.d553248635077608788-aaLodges.Travel-Guide-Accommodation) - [Mcdaniel Hotels](https://www.expedia.co.uk/McDaniel-Hotels.d6343444.Travel-Guide-Hotels) - [Neavitt Hotels](https://www.expedia.co.uk/Neavitt-Hotels.d3000347944.Travel-Guide-Hotels) - [North Beach Hotels](https://www.expedia.co.uk/North-Beach-Hotels.d138967.Travel-Guide-Hotels) - [Adults Only Resorts & in Oxford](https://www.expedia.co.uk/Oxford-Hotels-Adults-Only-Resorts.0-0-d142793-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Oxford](https://www.expedia.co.uk/Oxford-Hotels-Beach-Hotels.0-0-d142793-tBeachHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Oxford](https://www.expedia.co.uk/Oxford-Hotels-Spa-Hotels.0-0-d142793-tSpaHotels.Travel-Guide-Filter-Hotels) - [Oxford Hotels](https://www.expedia.co.uk/Oxford-Hotels.d142793.Travel-Guide-Hotels) - [Rose Haven Hotels](https://www.expedia.co.uk/Rose-Haven-Hotels.d153066.Travel-Guide-Hotels) - [Royal Oak Hotels](https://www.expedia.co.uk/Royal-Oak-Hotels.d6047042.Travel-Guide-Hotels) - [Shady Side Hotels](https://www.expedia.co.uk/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels) - [Hotels with Gym in St. Michaels](https://www.expedia.co.uk/St-Michaels-Hotels-Hotel-With-Gym.0-0-d5940-thotelwithgym.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in St. Michaels](https://www.expedia.co.uk/St-Michaels-Hotels-Hotels-With-Indoor-Pools.0-0-d5940-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in St. Michaels](https://www.expedia.co.uk/St-Michaels-Hotels-Pet-Friendly-Hotel.0-0-d5940-tPetFriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in St. Michaels](https://www.expedia.co.uk/St-Michaels-Hotels-Spa-Hotels.0-0-d5940-tSpaHotels.Travel-Guide-Filter-Hotels) - [St. Michaels Hotels](https://www.expedia.co.uk/St-Michaels-Hotels.d5940.Travel-Guide-Hotels) - [Gay-Friendly Hotels in Tilghman](https://www.expedia.co.uk/Tilghman-Hotels-Gay-Friendly-Hotel.0-0-d166219-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Tilghman Hotels](https://www.expedia.co.uk/Tilghman-Hotels.d166219.Travel-Guide-Hotels) - [Wittman Hotels](https://www.expedia.co.uk/Wittman-Hotels.d3000440946.Travel-Guide-Hotels) ### Flights - [Flights to Chesapeake Beach](https://www.expedia.co.uk/Cheap-Flights-To-Chesapeake-Beach.d88967.Travel-Guide-Flights) - [Flights to Kent Island](https://www.expedia.co.uk/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights) - [Flights to St. Michaels](https://www.expedia.co.uk/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights) - [Flights from Neavitt](https://www.expedia.co.uk/lp/flights/3000347944/flights-from-neavitt) - [Flights from Bozman](https://www.expedia.co.uk/lp/flights/3000440434/flights-from-bozman) - [Flights from Kent Island](https://www.expedia.co.uk/lp/flights/553248635077608788/flights-from-kent-island) - [Flights from St. Michaels](https://www.expedia.co.uk/lp/flights/5940/flights-from-st-michaels) - [Flights from Chesapeake Beach](https://www.expedia.co.uk/lp/flights/88967/flights-from-chesapeake-beach) ### Packages - [Andrews Air Force Base Holidays](https://www.expedia.co.uk/Andrews-Air-Force-Base.d553248622833027201.Holidays-City-Breaks) - [Annapolis Holidays](https://www.expedia.co.uk/Annapolis.d6034082.Holidays-City-Breaks) - [Blackwater National Wildlife Refuge](https://www.expedia.co.uk/Blackwater-National-Wildlife-Refuge-Maryland.d6340491.Attraction) - [Breezy Point Beach](https://www.expedia.co.uk/Breezy-Point-Beach-Chesapeake-Beach.d553248621532662089.Attraction) - [California Holidays](https://www.expedia.co.uk/California.d85533.Holidays-City-Breaks) - [Cambridge Holidays](https://www.expedia.co.uk/Cambridge.d6608.Holidays-City-Breaks) - [Capitol Heights Holidays](https://www.expedia.co.uk/Capitol-Heights.d7250.Holidays-City-Breaks) - [Chesapeake Beach Holidays](https://www.expedia.co.uk/Chesapeake-Beach.d88967.Holidays-City-Breaks) - [Visit Chesapeake Beach](https://www.expedia.co.uk/Chesapeake-Beach.dx88967) - [Choptank River Lighthouse](https://www.expedia.co.uk/Choptank-River-Lighthouse-Cambridge.d6286144.Attraction) - [Christ Episcopal Church](https://www.expedia.co.uk/Christ-Episcopal-Church-Downtown-Cambridge.d553248621532662093.Attraction) - [Clinton Holidays](https://www.expedia.co.uk/Clinton.d6523.Holidays-City-Breaks) - [Visit Deale](https://www.expedia.co.uk/Deale.dx55664) - [Eastern Shore Holidays](https://www.expedia.co.uk/Eastern-Shore.d6025644.Holidays-City-Breaks) - [Easton Holidays](https://www.expedia.co.uk/Easton.d7120.Holidays-City-Breaks) - [Fort Smallwood Park](https://www.expedia.co.uk/Fort-Smallwood-Park-Pasadena.d553248621532662358.Attraction) - [Hammond-Harwood House](https://www.expedia.co.uk/Hammond-Harwood-House-Historic-District.d6077396.Attraction) - [Harriet Tubman Birthplace Marker](https://www.expedia.co.uk/Harriet-Tubman-Birthplace-Marker-Cambridge.d553248621561879377.Attraction) - [Visit Kent Island](https://www.expedia.co.uk/Kent-Island.dx553248635077608788) - [Landover Holidays](https://www.expedia.co.uk/Landover.d10025.Holidays-City-Breaks) - [Lanham Holidays](https://www.expedia.co.uk/Lanham.d8533.Holidays-City-Breaks) - [Marley Holidays](https://www.expedia.co.uk/Marley.d130157.Holidays-City-Breaks) - [Maryland Quiet Waters Park](https://www.expedia.co.uk/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Attraction) - [Maryland Holidays](https://www.expedia.co.uk/Maryland.d222.Holidays-City-Breaks) - [Visit Oxford](https://www.expedia.co.uk/Oxford.dx142793) - [Richardson Maritime Museum](https://www.expedia.co.uk/Richardson-Maritime-Museum-Downtown-Cambridge.d553248621532662094.Attraction) - [Rock Hall Holidays](https://www.expedia.co.uk/Rock-Hall.d177447.Holidays-City-Breaks) - [Rose Haven Holidays](https://www.expedia.co.uk/Rose-Haven.d153066.Holidays-City-Breaks) - [Visit Rose Haven](https://www.expedia.co.uk/Rose-Haven.dx153066) - [Royal Oak Holidays](https://www.expedia.co.uk/Royal-Oak.d6047042.Holidays-City-Breaks) - [Visit Shady Side](https://www.expedia.co.uk/Shady-Side.dx6264943) - [Sotterley Plantation](https://www.expedia.co.uk/Sotterley-Plantation-Hollywood.d6324720.Attraction) - [Spocott Windmill](https://www.expedia.co.uk/Spocott-Windmill-Cambridge.d553248621532662092.Attraction) - [Visit St. Michaels](https://www.expedia.co.uk/St-Michaels.dx5940) - [U.s. Naval Academy](https://www.expedia.co.uk/US-Naval-Academy-Annapolis.d6077390.Attraction) - [Upper Yough River](https://www.expedia.co.uk/Upper-Yough-River-Friendship.d553248621532662254.Attraction) - [Waldorf Holidays](https://www.expedia.co.uk/Waldorf.d6057464.Holidays-City-Breaks) ### Cars - [Amigo Autos Rental Cars in Kent Island](https://www.expedia.co.uk/Amigo-Autos-Car-Rentals-In-Kent-Island.d553248635077608788-c1128.Car-Rental-Guide-Suppliers) - [Car hire Deale](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Deale.d55664.Car-Hire-Guide) - [Car hire near Kent Island](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Kent-Island.d553248635077608788.Car-Hire-Guide) - [Car hire Oxford](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Oxford.d142793.Car-Hire-Guide) - [Car hire St. Michaels](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-St-Michaels.d5940.Car-Hire-Guide) - [Enterprise Rental Cars in St. Michaels](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-St-Michaels.d5940-c15.Car-Rental-Guide-Suppliers) - [Firefly Portugal Rental Cars in Kent Island](https://www.expedia.co.uk/Firefly-Portugal-Car-Rentals-In-Kent-Island.d553248635077608788-c1071.Car-Rental-Guide-Suppliers) - [Pickup Car Hire in Oxford](https://www.expedia.co.uk/Pickup-Car-Rentals-In-Oxford.d142793-tPickup.Car-Rental-Guide-Class) - [United Rental Cars in Kent Island](https://www.expedia.co.uk/United-Car-Rentals-In-Kent-Island.d553248635077608788-c1088.Car-Rental-Guide-Suppliers) ### Holiday Homes - [Chesapeake Beach Holiday Rentals](https://www.expedia.co.uk/Chesapeake-Beach-Holiday-Rentals.d88967.Travel-Guide-HolidayRentals) - [Kent Island Holiday Rentals](https://www.expedia.co.uk/Kent-Island-Holiday-Rentals.d553248635077608788.Travel-Guide-HolidayRentals) - [Oxford Holiday Rentals](https://www.expedia.co.uk/Oxford-Holiday-Rentals.d142793.Travel-Guide-HolidayRentals) - [Rose Haven Holiday Rentals](https://www.expedia.co.uk/Rose-Haven-Holiday-Rentals.d153066.Travel-Guide-HolidayRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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