Title: Chester Guest Houses from CA $482 | 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) ![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 prices for these dates Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester guest houses ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101170000/101168900/101168894/0c10112b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101170000/101168900/101168894/f9bd711a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101170000/101168900/101168894/78170267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101170000/101168900/101168894/bc9d2cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverview Retreat on Warehouse Creek - sleeps 6 [](https://www.expedia.ca/Edgewater-Hotels-Riverview-Retreat-On-Warehouse-Creek.h101168894.Hotel-Information) Edgewater 10/10 Exceptional (34 reviews) "The host was extremely welcoming and the place was beautiful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $177 CA $660 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Edgewater-Hotels-Riverview-Retreat-On-Warehouse-Creek.h101168894.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71430000/71421600/71421575/20d3f7cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71430000/71421600/71421575/f66467d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71430000/71421600/71421575/d36e561b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71430000/71421600/71421575/b0a7e139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis [](https://www.expedia.ca/Annapolis-Hotels-West-Annapolis-Hidden-Gem-75Mile-To-Navy-Stadium-1Mile-To-Downtown-Annapolis.h71421575.Hotel-Information) Homewood 10/10 Exceptional (21 reviews) "Loved the stay here. Such a nice cute spot and so close to everything we needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan A. CA $172 CA $482 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Annapolis-Hotels-West-Annapolis-Hidden-Gem-75Mile-To-Navy-Stadium-1Mile-To-Downtown-Annapolis.h71421575.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=2026-04-01&endDate=2026-04-02®ionId=3000440455&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d3000440455-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Guest-Houses.d3000440455-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "This hotel were one of the best, I have stayed at numerous Hyatt regencies and all of them makes the grade. But this Hyatt with the view of the river puts it over the top. The staff was very nice and very knowledgeable and also very helpful. I recommend Hyatt hotels in general but I especially recommend this Hyatt in Kent Narrows " [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Was very clean and comfortable. Staff was accomidationg." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 8/10 Good "It was wonderful having the suite on this visit, a separate room & chair for late night tv so as not to disturb my husband." [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Clean room" [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg) ### Sonesta ES Suites Annapolis 8/10 Good "I have stayed here twice and this is a really great hotel to stay at. They also have breakfast which is great too. " [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "The man working the front desk when I arrived was very friendly and helpful. He is a great part of your team. I only regret that I do not remember his name. " [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Fairfield Inn & Suites By Marriott Annapolis](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/676e246c_y.jpg) ### Fairfield Inn & Suites By Marriott Annapolis 10/10 Excellent "Would stay here again! Everyone and everything including location was excellent!" [](https://expedia.ca/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open." [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ## Find out more about Chester ## Chester Guest Houses information | Number of reviews | 55 | | ----------------- | -------------- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $482 | | Highest Price | CA $660 | ## 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) - 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