Title: Chester Travel Guide: Best of Chester, Maryland Travel 2026 | Expedia.co.uk [Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d3000440455.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d3000440455.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d3000440455.Holidays-City-Breaks) # Chester Travel Guide ## Tourist Guide ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Chester Things to do - Top hotels in Chester - Top Holiday Rentals in Chester ![Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/409af264_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! Chester MD Stay at this family-friendly holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake ... 9.8/10 Exceptional! (94 reviews) Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.. Reviewed on 14 Sept 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) ![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 Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (1,885 reviews) Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back! Reviewed on 31 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) ![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 £133 23 Feb - 24 Feb includes taxes & fees Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the bar and the helpful ... 9.2/10 Wonderful! (1,002 reviews) Room was clean. Beds were comfy. Very walkable to all of the hot spots. Parking was expensive onsite. Reviewed on 4 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true®ionId=3000440455) [See all 1,204 properties in Chester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=3000440455) 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. ![Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!](https://images.trvl-media.com/lodging/34000000/33560000/33554400/33554342/409af264_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! Chester MD Stay at this family-friendly holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake ... 9.8/10 Exceptional! (94 reviews) Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.. Reviewed on 14 Sept 2025 [](https://expedia.co.uk/Chester-Hotels-Waterfront-Home-On-3-Acres-Fish.h33554342.Hotel-Information) ![The Blue Crab Beach House - Free beach passes ](https://images.trvl-media.com/lodging/79000000/78610000/78601600/78601522/6054db72_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Blue Crab Beach House - Free beach passes North Beach MD Stay at this holiday home in North Beach. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ... 10/10 Exceptional! (78 reviews) Everything was fine and comfortable Reviewed on 27 Dec 2025 [](https://expedia.co.uk/North-Beach-Hotels-The-Blue-Crab-Beach-House.h78601522.Hotel-Information) ![421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!](https://images.trvl-media.com/lodging/67000000/66850000/66845500/66845427/e45263c6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking! Annapolis MD Stay at this holiday home in Annapolis. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the pool in their reviews. Popular attractions ... 10/10 Exceptional! (129 reviews) Great host! Great house! Reviewed on 2 Jan 2026 [](https://expedia.co.uk/Annapolis-Hotels-421-Irie-Simply-Charming-2-Story-Cottage-Private-Pool-1-Off-Street-Parking.h66845427.Hotel-Information) [See all properties in Chester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=3000440455&sort=VACATION_RENTAL) 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. ## Check Chester hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-08&endDate=2026-02-09)[8 Feb - 9 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-08&endDate=2026-02-09) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-09&endDate=2026-02-10)[9 Feb - 10 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-09&endDate=2026-02-10) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[13 Feb - 15 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) ### Popular places to visit #### Chesapeake Exploration Center Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants. [](https://expedia.co.uk/Chesapeake-Exploration-Center-Chester.d553248621561879491.Attraction) - Cities near Chester - Places of interest - [U.S. Naval Academy ](https://expedia.co.uk/US-Naval-Academy-Annapolis.d6077390.Attraction) - [Chesapeake Bay ](https://expedia.co.uk/Chesapeake-Bay-United-States-of-America.d6056980.Attraction) - [Maryland Quiet Waters Park ](https://expedia.co.uk/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Attraction) - [Northern Chesapeake Bay ](https://expedia.co.uk/Northern-Chesapeake-Bay-Maryland.d6051456.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app