Title: 2 Stars Hotels in Chester, Maryland from CA $105 - Find Cheap Chester Hotels With 2 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 # 2 Stars Hotels in Chester, Maryland from CA $105 - ![](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 2 Star Hotels Tonight [Dec 21 - Dec 22](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-21&endDate=2025-12-22&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-22&endDate=2025-12-23&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester 2-star hotels ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/bc6750c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ee980eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5eb26742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) St. Michaels 8.2/10 Very good (1001) "Staff was friendly, courteous, and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $131 CA $145 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/05aa05a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/84264c8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/80c6d100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) Annapolis 7.8/10 Good (1003) "Best Western provided a clean comfortable room for our stay at Annapolis. There was plentiful parking and the staff was courteous and helpful. The breakfast was adequate and centrally located. I would definitely recommends this establishment" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $92 CA $105 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/a336329e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/1f23d418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/e600218e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) Annapolis 8.2/10 Very good (1003) "I had a great experience at my stay at Hampton " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Idris O CA $123 CA $141 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/aabb28e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f74ef80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/fa54a5ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9ee94703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Annapolis by IHG [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) Annapolis 8.8/10 Excellent (181) "The staff was extremely pleasant and enjoyable to work with!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $121 CA $138 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/bb752da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/758b9b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very good (1002) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tucker T CA $115 CA $128 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/a97c1669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/e0e2d461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/21c5252e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn [](https://www.expedia.ca/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) Easton 7.6/10 Good (826) "Everything was clean; staff friendly; breakfast great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $111 CA $123 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/c52c5ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/3a599b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/ec18bd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Easton Inn & Suites [](https://www.expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) Easton 9.2/10 Wonderful (1002) "Spacious room, friendly staff, nice bathroom. Everyone is very accommodating." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA CA $164 CA $181 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) ![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/7b97c3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville near Kent Island [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (863) "room was nice breakfast was good and the staff was very friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Esai CA $117 CA $130 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (936) "It was very comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $120 CA $133 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/8260c7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/w1504h992x0y8-f18eeee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/d2bab96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/15cfa9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Easton [](https://www.expedia.ca/Easton-Hotels-Hampton-Inn-Easton.h1432437.Hotel-Information) Easton 9.0/10 Wonderful (553) "all excellent with kudos to staff and the breakfast cook." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOSEPH CA $165 CA $182 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Easton-Hotels-Hampton-Inn-Easton.h1432437.Hotel-Information) ![Fridge, microwave](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/8f46f567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/335c1120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/b510cc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/bf93fe2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Village Inn Annapolis MD [](https://www.expedia.ca/Annapolis-Hotels-Village-Inn.h530229.Hotel-Information) Annapolis 6.2/10 (508) "The room was very nice, clean and quiet. Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William [](https://www.expedia.ca/Annapolis-Hotels-Village-Inn.h530229.Hotel-Information) ![Superior Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower) | Bathroom](https://images.trvl-media.com/lodging/22000000/21670000/21664700/21664671/ab1e52fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21670000/21664700/21664671/0ea9ffb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/22000000/21670000/21664700/21664671/8de9a68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21670000/21664700/21664671/6797349a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Red-Roof-Inn-Annapolis.h21664671.Hotel-Information) Annapolis 7.0/10 Good (409) "Stayed one night. Did the job." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $97 CA $110 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Annapolis-Hotels-Red-Roof-Inn-Annapolis.h21664671.Hotel-Information) ![Room, 1 King Bed, Non Smoking (Whirlpool)](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/21b35d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/59ba3f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/72559fa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/5f8f1383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Annapolis by IHG [](https://www.expedia.ca/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) Annapolis 8.2/10 Very good (1001) "Clean room and friendly staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Silvia CA $110 CA $126 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/1068537c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/14b7e845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/da259258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8dfe0c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchored Inn at Hidden Harbour Marina [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) Deale 9.4/10 Exceptional (470) "Beautiful place to stay, we stay their one to two times a year." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marjorie CA $185 CA $211 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/4be52931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/d6387655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/742b0988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wildset [](https://www.expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) Downtown St. Michaels 9.8/10 Exceptional (410) "Well decorated inn w spacious and clean rooms, walking distance to shops, great restaurant with bar & breakfast included. Would absolutely come back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenn CA $261 CA $317 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/13000000/12010000/12009900/12009838/2322f180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/13000000/12010000/12009900/12009838/eedc74e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/13000000/12010000/12009900/12009838/6e7eb9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/13000000/12010000/12009900/12009838/7f968da2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Easton [](https://www.expedia.ca/Easton-Hotels-Fairfield-Inn-Suites-By-Marriott-Easton.h12009838.Hotel-Information) Easton 9.6/10 Exceptional (367) "Great hotel, very clean & quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet CA $222 CA $244 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Easton-Hotels-Fairfield-Inn-Suites-By-Marriott-Easton.h12009838.Hotel-Information) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/30000/20500/20442/6bfb162c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20442/139228f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20500/20442/41c1c106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20442/w2870h1923x10y0-90479fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Easton Route 50 [](https://www.expedia.ca/Easton-Hotels-Econo-Lodge-Easton-Route-50.h20442.Hotel-Information) Easton 6.6/10 (386) "Staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andre CA $112 CA $123 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Easton-Hotels-Econo-Lodge-Easton-Route-50.h20442.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/1976e6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/3b6079a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/2624f48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/0ead9534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) Annapolis 9.8/10 Exceptional (32) "Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ian [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/c982427d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/8af764c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Suite | Living area](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0787536d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/6e7f4df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) Tilghman 8.8/10 Excellent (90) "Very relaxing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $163 CA $240 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/97119172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, City View](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/34bda8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/8d2066be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) Historic District 10/10 Exceptional (3) "Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels." ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Jo CA $445 CA $508 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.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%2F2Star-Chester-Hotels.s20-0-d3000440455.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Chester-Hotels.s20-0-d3000440455.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Chester. ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Historic Inns of Annapolis 58 State Circle Annapolis MD [Get rates](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=3000440455) 8.8/10 Excellent! (1,902 reviews) [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta ES Suites Annapolis 170 Admiral Cochrane Dr Edgewater MD CA $126 CA $143 total Jan 11 - Jan 12, 2026 includes taxes & fees 8.8/10 Excellent! (964 reviews) [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Country Inn & Suites by Radisson, Annapolis, MD 2600 Housley Road Annapolis MD CA $137 CA $156 total Jan 11 - Jan 12, 2026 includes taxes & fees 9/10 Wonderful! (1,005 reviews) [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=3000440455&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=3000440455&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=3000440455&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=3000440455&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=3000440455&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=22%2F12%2F2025&endDate=23%2F12%2F2025®ionId=3000440455&star=20&star=20&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=2026-01-04&endDate=2026-01-05&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 ## Find out more about Chester Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Chester, Chester you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in Chester are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. 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