Title: Visit Chester: Best of Chester Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000440455.Destination-Travel-Guides) # Chester ## Travel 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 - Chester Hotel Deals - Vacation 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 Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ... 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 Sep 14, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=33554342&PinnedHotelID=33554342&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%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 Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ... 9/10 Wonderful! (1,883 reviews) Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back! Reviewed on Jan 31, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) ![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 CA $112 CA $128 total Feb 22 - Feb 23 includes taxes & fees Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ... 8.6/10 Excellent! (1,005 reviews) Staff-clean room Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true®ionId=3000440455) [See all 1,202 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=11%2F02%2F2026&endDate=12%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 Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay ... 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 Sep 14, 2025 [](https://expedia.ca/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 vacation home in North Beach. Enjoy free WiFi, 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 Dec 27, 2025 [](https://expedia.ca/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 vacation home in Annapolis. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the pool in our reviews. Popular attractions ... 10/10 Exceptional! (129 reviews) Great host! Great house! Reviewed on Jan 2, 2026 [](https://expedia.ca/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.ca/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.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-10&endDate=2026-02-11) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=2026-02-11&endDate=2026-02-12) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440455&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) ### Popular places to visit #### Chesapeake Exploration Center Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants. [](https://expedia.ca/Chesapeake-Exploration-Center-Chester.d553248621561879491.Vacation-Attraction) - Cities near Chester - Places of interest - [Chesapeake Exploration Center ](https://expedia.ca/Chesapeake-Exploration-Center-Chester.d553248621561879491.Vacation-Attraction) - [U.S. Naval Academy ](https://expedia.ca/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction) - [Chesapeake Bay ](https://expedia.ca/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Chesapeake Bay Bridge ](https://expedia.ca/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) - [Sandy Point State Park ](https://expedia.ca/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction) - [Maryland State House ](https://expedia.ca/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction) - [Maryland Quiet Waters Park ](https://expedia.ca/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.ca/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) - [Kunta Kinte–Alex Haley Memorial ](https://expedia.ca/Kunta-KinteAlex-Haley-Memorial-Annapolis.d553248621533116849.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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