Title: Chester Inns from CA $313 | 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) ![](https://mediaim.expedia.com/destination/2/5fdecfa9ea611e8f8d02038dea5d1c0a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Search Inns in Chester from CA $313 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Inns ![Outdoor banquet area](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/w2877h1800x0y0-f772721c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Double Queen First Level - Dog Friendly | View from room](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/0c190249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/b30d5f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/ee1a612d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tilghman Island Inn Tilghman 9.6/10 Exceptional (110) "Great staff and food!" CA $285 CA $313 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1080000/1073600/1073536/b4986d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, ocean views ](https://images.trvl-media.com/lodging/2000000/1080000/1073600/1073536/8fa719b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1080000/1073600/1073536/3240672f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1073600/1073536/56bd6ac0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lowes Wharf Marina Inn Sherwood 7.8/10 Good (71) "Very relaxing ( we were there midweek). Incredible location and sunsets." [](https://www.expedia.ca/Sherwood-Hotels-Lowes-Wharf-Marina-Inn.h1073536.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24270000/24269400/24269398/95fa6af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room (Choptank)](https://images.trvl-media.com/lodging/25000000/24270000/24269400/24269398/14c12874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/25000000/24270000/24269400/24269398/80ff456c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room (Rose Suite)](https://images.trvl-media.com/lodging/25000000/24270000/24269400/24269398/13da5a92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oxford Inn Oxford 9.4/10 Exceptional (237) "Had a wonderful weekend and fully enjoyed the accommodations and breakfast " [](https://www.expedia.ca/Oxford-Hotels-The-Oxford-Inn.h24269398.Hotel-Information) ![Dinner served](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/be8a1621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/w264h344x4y2-b20fcf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/82384fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/20605cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at 202 Dover Easton 10/10 Exceptional (14) "Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience." [](https://www.expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-09&endDate=2025-10-10®ionId=3000440455&adults=2&lodging=INN&sort=RECOMMENDED&openPlayBack=true) ![](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%2FChester-Inns.d3000440455-aaInns.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Inns.d3000440455-aaInns.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Courtyard by Marriott Annapolis](//images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "Extremely cozy. Felt good to just relax." [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ![Candlewood Suites Annapolis by IHG](//images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9088c5e1_y.jpg) ### Candlewood Suites Annapolis by IHG 10/10 Excellent "Nice area, clean, comfortable, pleasant staff" [](https://expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "My wife and were away to celebrate our 34th wedding anniversary and the stay was close to home affordable and very comfortable. Hotel staff was very friendly and welcoming " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hilton Garden Inn Annapolis](//images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc_y.jpg) ### Hilton Garden Inn Annapolis 10/10 Excellent "Our stay at the hotel was easy check in and check out. Quiet and great location for our stay." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "No additional comment. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](//images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "I was perfect for our visit. Close to everything." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Stayed for one night; room was nice, easy to access, and located near numerous local attractions. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Room was very clean, bed was extremely comfortable!!! Modest hotel but well worth the money! Breakfast was awesome!!! Highly recommended! Will stay here again!" [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ## Find out more about Chester ## Chester Inns information | Number of reviews | 110 | | --- | --- | | Accommodation | 4 Inns | | Lowest Price | CA $313 | | Highest Price | CA $313 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Kent Island](https://www.expedia.ca/5Star-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Stevensville](https://www.expedia.ca/5Star-Stevensville-Hotels.s50-0-d162393.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Adults-Only-Resorts.0-n553248635976473602-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Boutique-Hotel.0-n553248635976473602-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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