Title: 4 Stars Hotels in Chester, Maryland from CA $118 - Find Cheap Chester Hotels With 4 Stars | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx3000440455)[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)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d3000440455.Travel-Guide-Flights)[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) ![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=1200&h=500&q=medium) Photo by Patricia Knorr ![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester 4 Star Hotels Tonight [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-18&endDate=2026-01-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-19&endDate=2026-01-20&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-30&endDate=2026-02-01&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester 4-star hotels ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/c21b600a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,002 reviews) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Miguel CA $104 CA $118 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/48975360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Annapolis 9.4/10 Exceptional (1,003 reviews) "Pleasant staff. Good location to walk to restaurants, shops. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $204 CA $233 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/fb8e8cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/4dba2228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) Historic District 8.8/10 Excellent (898 reviews) "Great location, nice and clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Micah CA $259 CA $295 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/96f9cffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, City View](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/c301dc98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) Annapolis 8.8/10 Excellent (1,003 reviews) "Great hotel love that they are pet friendly. Easy check in and valet parking staff great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $207 CA $236 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/0fbfe277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Single Room](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (434 reviews) "Amazing rooms and service!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia CA $217 CA $276 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/18678d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/6aa17d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom, Balcony | Balcony view](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/1f0e0a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d1a8f617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) Easton 10/10 Exceptional (41 reviews) " Beautiful property, wonderful staff, excellent food service." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Seth CA $575 CA $632 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chester-Hotels.s40-0-d3000440455.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chester-Hotels.s40-0-d3000440455.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester. ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn at Perry Cabin 308 Watkins Ln St. Michaels MD CA $714 CA $785 total Jan 22 - Jan 23 includes taxes & fees 9.4/10 Exceptional! (373 reviews) [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![The Inn at Tacaro Estate](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Tacaro Estate 6220 Town Point Rd Tracys Landing MD [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=96042430&PinnedHotelID=96042430&HadPinnedHotel=true®ionId=3000440455) 9.2/10 Wonderful! (11 reviews) [](https://expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![Inn at 202 Dover](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/be8a1621_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn at 202 Dover 202 East Dover Street Easton MD [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=5308723&PinnedHotelID=5308723&HadPinnedHotel=true®ionId=3000440455) [](https://expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) Still don't see what you're looking for? [See all properties in Chester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=3000440455&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=3000440455&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=3000440455&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=3000440455&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=3000440455&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=3000440455&star=40&star=40&amenities=WATER_PARK) 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. ## Learn more about Chester Chester awaits: its island views, sunny weather, golf, and more! [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-01&endDate=2026-02-02&adults=2®ionId=3000440455) ![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=900&h=547&p=1&q=high) Photo by Patricia Knorr ## Top Chester Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Very nice and neat hotel in good location. Staff are wonderful" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Very welcoming and room very clean." [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "We were able to get there an hour early and our room was ready and the staff were great!" [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Pleasant staff. Good location to walk to restaurants, shops. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![The Inn at Chesapeake Bay Beach Club](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e_y.jpg) ### The Inn at Chesapeake Bay Beach Club 10/10 Excellent "We had a wonderful stay at the Chesapeake Bay Beach Club and couldn’t have asked for a better place to celebrate our 3rd anniversary. From the moment we arrived, the staff was fantastic—friendly, welcoming, and genuinely attentive throughout our stay. Our room was very nice, clean, and well maintained, making it easy to relax and enjoy the experience. While the bed was a little softer than my personal preference, it certainly didn’t take away from our stay and isn’t something I’d count as a negative. The restaurant was outstanding. The food was excellent, beautifully prepared, and truly elevated the entire experience. It was the perfect complement to an already memorable getaway. Overall, we thoroughly enjoyed our time here and would absolutely recommend the Chesapeake Bay Beach Club to anyone looking for a relaxing, high-quality stay—especially for a special occasion. We’re already looking forward to coming back." [](https://expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ## Find out more about Chester If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### What are the best 4-star hotels in Chester? ### How much does it cost to stay in a 4-star hotel in Chester? > - Search for the lowest price from CA $785 ### What's the difference between 5-star and 4-star hotels in Chester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [1 Star Hotels in Holabird Industrial Park ](https://www.expedia.ca/1Star-Holabird-Industrial-Park-Baltimore-Hotels.s10-n553248635976387003-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Graceland Park ](https://www.expedia.ca/3Star-Graceland-Park-Baltimore-Hotels.s30-n553248635976385043-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Pleasant View Gardens ](https://www.expedia.ca/3Star-Pleasant-View-Gardens-Baltimore-Hotels.s30-n553248635976385030-0.Travel-Guide-Filter-Hotels) - 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