Title: Chester Condo Rentals from CA $516 | 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 Condos Rentals in Chester from CA $516 - ![](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 [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Condo Rentals ![Interior](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/a768e65e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/38d6910b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/f86ddc27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/3ab90a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale Condo in Annapolis Historic District 10/10 Exceptional (1) "The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer H. CA $401 CA $846 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/3d98a748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/876912bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/a6db755d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/d953bc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Downtown Annapolis Condo With Free Parking Historic District 10/10 Exceptional (33) "The apartment is exactly what we expected and was a great place to stay! Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan U. CA $209 CA $516 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Annapolis-Hotels-Downtown-Annapolis-Condo-W-Free-Parking-Coffee.h69666468.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=2025-11-29&endDate=2025-11-30®ionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style 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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APARTMENT) Cabins [](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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=CABIN) 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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=COTTAGE) 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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VILLA) 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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VACATION_HOME) 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=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=HOUSE_BOAT) ![](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-Condos.d3000440455-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Condos.d3000440455-aaCondos.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "The room was very clean, the staff were very nice. Great location." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "The room was super clean and tidy. The check in clerk was very friendly and welcoming. We will likely stay again." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Everything " [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ### Hampton Inn & Suites Annapolis 10/10 Excellent "Front desk manager, when we arrived, was very courteous and on top of everything. " [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent "Very clean hotel and convenient hotel location. Priced right, clise to d I wntown Annapolis and Town Center. Staff was superb " [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Nice big rooms, comfortable beds. Well maintained. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "Wonderful country inn!" [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Overall... everything was good." [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ### Sonesta ES Suites Annapolis 10/10 Excellent "This was the first time I stayed at a Sonesta property. It was excellent. The staff at the front desk were all friendly and courteous.the lobby area smells amazing!! The room was spacious with a complete kitchen. I will definitely be staying at Sonesta again. " [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ## Find out more about Chester ## Chester Condo Rentals information | Number of reviews | 31 | | --- | --- | | Accommodation | 10 Condo Rentals | | Lowest Price | CA $516 | | Highest Price | CA $846 | ## Frequently asked questions ### Why book your condo in Chester with Expedia? > Expedia will help you find your dream condo in Chester. After a luxury escape? Use our filters to search for properties that have a 5-star rating. If you're on a budget, click on how much you want to spend and then browse our amazing deals. We'll help you find the perfect pad whatever your plans or bank balance. ### How can I find cheap condos in Chester? > With Expedia's user-friendly filter tool, booking cheap condos in Chester is easy. 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