Title: Chester Cottages from CA $388 | 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 # Search Chester Cottage Rentals from CA $388 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Cottages ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/w1179h1552x0y10-4ae4c675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/6b784e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/a52717e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/d32606e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in North Beach 10/10 Exceptional (1) "Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Georgina P. CA $180 CA $388 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/North-Beach-Hotels-Charming-2-Bedroom-1-Bath-Cottage-With-AC.h114309947.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/fa37e440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/37ea1a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/3508a401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/dcb17a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Stevensville 10/10 Exceptional (6) "Beautiful home. Very nice and quiet neighborhood on the water. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shannan t. CA $560 CA $1,241 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Stevensville-Hotels-Charming-2-Bedroom-Waterfront-Cottage-In-Peaceful-Stevensville-With-AC.h108008595.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/8b7ab73b.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/e6912d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pasadena 9.6/10 Exceptional (22) "Excellent Property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Buu T. CA $505 CA $932 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information) ![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) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w905h683x60y0-0737769d.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) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w816h682x104y0-a072a320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Historic District 9.6/10 Exceptional (16) "We had a very lovely stay . This is an excellent location . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly B. CA $631 CA $1,051 total includes taxes & fees Dec 1 - Dec 2 [](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=2025-12-12&endDate=2025-12-13®ionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_3000440455) ![](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 ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "The hotel was very clean, and staff was courteous and helpful " [](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/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "The staff was excellent and friendly." [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.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 "Clean older rooms. Quite comfortable. Rick at the front desk was a superstar! Knowledgeable, and friendly. Great example for the younger staff. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "I have stayed several times over the last month or so totaling at leadt 7 nights and during every stay i have had a great experiene. Particularly with Chrissy who ive seen maonly during the night shift. Cannot understate how helpful and pleasant she has been. Probably the reason i wont stay anywhere else(if theres availability) in and around the Annapolis area. Keep up the amazing customer service!! 5 STARS " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Nice clean room. Good breakfast. Ample free parking." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.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 "The room was clean and the amenities were great! I loved the lobby and valet very fast and professional. I will stay here again. " [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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 "Location perfect " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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 "Pretty good value. Good shower pressure, practically enough to pelt your skin off! Breakfast had a good variety, though the eggs were a strange texture. The waffle maker was nice. The hot tub was hot and fairly clean, though the jets were so forceful and chaotic it was kind of difficult to sit anywhere near them. Overall, good value" [](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 15 | | --- | --- | | Accommodation | 89 Cottages | | Lowest Price | CA $388 | | Highest Price | CA $1,241 | ## Frequently asked questions ### How much do cottages in Chester cost? > Rates for cottages in Chester range between CA $388 and CA $1,241 per night. No matter your budget, you'll find the ideal place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Why book your cottage in Chester with Expedia? > We think that vacays should be a piece of cake, so if you're in search of cottages in Chester at a great price, Expedia is here to help. Keep the budget in check and go for a wallet-friendly option far from the hustle and bustle, or book a 5-star cottage to spoil the ones you love most. ### How can I find cheap cottages in Chester? > With Expedia's handy filter tool, getting your hands on cheap cottages in Chester is easy. 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[Stevensville Vacation Rentals](https://www.expedia.ca/Stevensville-Vacation-Rentals.d162393.Travel-Guide-VacationRentals) - [Book Cottages in Chester on Expedia.com](https://www.expedia.com/Chester-Cottages.d3000440455-aaCottages.Travel-Guide-Accommodation)