Title: Chester Cottages from CA $799 | 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 In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester cottages ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/8b7ab73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/2f9f691d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/a2c5e148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/90-1f5b873c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Cottages- 2 Quaint Waterfront Retreats [](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information) Pasadena 9.6/10 Exceptional (22 reviews) "Excellent Property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Buu T. CA $491 CA $907 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h447x0y118-8b5ab4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w950h680x38y3-96439ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w951h680x36y3-968871c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h640x0y22-f248bc40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Cozy Cottage in Historic Downtown [](https://www.expedia.ca/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information) Historic District 9.6/10 Exceptional (16 reviews) "This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda Q. CA $446 CA $799 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.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=2026-03-15&endDate=2026-03-16®ionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_3000440455) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=COTTAGE) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=HOUSE_BOAT) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-05-30&d1=2026-05-30&endDate=2026-06-02&d2=2026-06-02&lodging=VILLA) ![](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-Cottages.d3000440455-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d3000440455-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Everyone was friendly, the room was great, and even though the Inn was going through some renovations i did not find my stay impacted by them at all. Breakfast was still delicious and I never wanted for anything." [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Perfect location, comfortable bed, clean and spacious room, cheap parking around the corner that was recommended by the staff. " [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Courtyard by Marriott Annapolis](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "Outstanding the room was wonderful. We had a king suite with a balcony very clean. The staff was also wonderful and very informative of the area. Hubby stayed for one night for his birthday will return. " [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "Friendly staff, clean rooms, clean public areas." [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![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 "The staff was very helpful. The room was nice and there were shops & restaurants nearby." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg) ### Candlewood Suites Annapolis by IHG 10/10 Excellent "The room was updated, very clean, and comfortable. " [](https://expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg) ### Best Western Kent Narrows Inn 10/10 Excellent "Clean room, hot water, huge breakfast, indoor pool, definitely an inexpensive nice place to stay just over the Bay on Na Shore, walking distance to Kent Narrows Airport " [](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Such a cool place to stay! Water pressure wasn’t great but it’s a very old building. " [](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) ### Sonesta ES Suites Annapolis 10/10 Excellent "We had a great time here. The room was bright, clean, warm and fully stocked with everything we needed! The fireplace was a bonus! Close to all types of activities and food, but really serene and quiet. I will stay here again. " [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 16 | | ----------------- | ----------- | | Accommodation | 89 Cottages | | Lowest Price | CA $799 | | Highest Price | CA $907 | ## Frequently asked questions ### How much do cottages in Chester cost? ### Why book your cottage in Chester with Expedia? ### How can I find cheap cottages in Chester? ## 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) - 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