Title: Chester Apartment Rentals from CA $208 | 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 Apartment Rentals in Chester ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Apartments ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown 9.6/10 Exceptional (105) "A charming studio in a quiet neighborhood. great directions from host on how to use the property - " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $126 CA $208 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b4e88275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/daf32ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/129d1b07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/26511092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4! Rock Hall 10/10 Exceptional (17) "I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy S. CA $165 CA $398 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/45c5363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/218670ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/777b4d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/4f776335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Pool Loft sleeps 4 Cape Saint Claire 10/10 Exceptional (3) "This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana S. CA $175 CA $496 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/f520f52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0e2deec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Oasis of Annapolis Star Annapolis 10/10 Exceptional (81) "Owners were great hosts. Loved this property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $378 CA $692 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1014h600x10y12-4e8a8c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w904h683x60y0-dec863ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1024h592x0y17-9d1e8161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/001f8463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 18th Cent. Charm in Historic Downtown Annapolis Historic District 9.0/10 Wonderful (12) "Property description is accurate, host is quickly responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradford R. CA $239 CA $482 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Annapolis-Hotels-Charming-18th-Cent-Home-In-Historic-Downtown-Annapolis.h92564827.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/27a8090f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/w1200h799x0y1-55bb08bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/2d43a6e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/697fbff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Gem: Stylish and Cozy Annapolis 10/10 Exceptional (2) "Clean and nicely decorated. Did not realize it was a basement unit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy B. CA $346 CA $678 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/14451366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/w1200h798x0y13-06d6d7c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/f407739a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/w1199h800x1y0-94cb1016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dean Street's Lower Deck House! Historic District 10/10 Exceptional (2) "We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaniel R. CA $295 CA $635 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Annapolis-Hotels-Dean-Streets-Lower-Deck-House.h117630208.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/w1201h914x0y1-e8fa6c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/658833c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/4478d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/dee76b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids Admiral Heights 10/10 Exceptional (45) "I loved the hosts. Very personable, accomodating with great communication. I plan to work with them again next time we come to Annapolis. Especially for Navy home football games. Perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $535 CA $697 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Annapolis-Hotels-Gorgeous-Carriage-House-Close-To-USNA.h87576375.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=2025-11-11&endDate=2025-11-12®ionId=3000440455&adults=2&lodging=APARTMENT&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-Apartments.d3000440455-aaApartments.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Apartments.d3000440455-aaApartments.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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 "Clean room, great staff, great breakfast " [](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 "Close to Annapolis Shopping Mall where you will find multiple restaurants and restaurants. The hotel is well kept with comfortable and clean rooms. An excellent price for the service received. " [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Hampton Inn & Suites Annapolis](//images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "." [](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 "We received excellent service and our needs were cared for. The hotel's WiFi went on tne fritz on Thursday but was fully restored by Thursday night. The staff was friendly and helpful. When were surprised with parking charges, the manager agreed to waive them. A good experience throughout our stay of more than a week." [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.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 "First time staying here, Hotel staff were amazing, hotel was so welcoming and clean, our room was perfect. Loved the jetted tub, perfect for 2, and the fireplace set the tone for a great stay. Shower was huge, and so was our room. Breakfast was hot and delicious. Made for a great couple's getaway. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 "Staff was amazing..Staff keep all of the area clean Staff is amazing.." [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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 "The staff were exceedingly helpful and friendly. Parking was close and easy." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "I enjoyed my stay at Hilton Garden Inn Annapolis. The room was comfortable and clean. I had a delicious breakfast sandwich. And it was nice to have a big, convenient parking lot." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) ![The Westin Annapolis](//images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "All was good " [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ## Find out more about Chester ## Chester Apartments information | Number of reviews | 260 | | --- | --- | | Accommodation | 80 Apartments | | Lowest Price | CA $208 | | Highest Price | CA $697 | ## Frequently asked questions ### What's it like to stay at an apartment in Chester? > You'll find 13 hotels and other accommodations in Chester. Though there aren't many apartments, we can help you search for accommodations that are similar. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can also filter by similar properties such as condos, vacation homes, or cottages. ### How do you know if an apartment is the best choice for you? > Often offering more space than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in at night and plan out their next day. ### What's the top apartment for a stay in Chester? > Listed below are some of the favorite apartments in the area: [Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!](https://www.expedia.ca/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information): Located 11.5 mi/18.5 km away in Rock Hall. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. [Riverfront Retreat 7mil from MD Renaissance Fest!](https://www.expedia.ca/Riva-Hotels-Riverfront-Retreat-7mil-From-MD-Renaissance-Fest.h74420621.Hotel-Information): It's located in Riva, 16 mi/25.7 km away. [18th Cent. Charm in Historic Downtown Annapolis](https://www.expedia.ca/Annapolis-Hotels-Charming-18th-Cent-Home-In-Historic-Downtown-Annapolis.h92564827.Hotel-Information): Located 10.7 mi/17.3 km away in Annapolis. Free WiFi, private patios, and fireplaces are included. Onsite laundry facilities and a game room are on site. [First Floor Studio Apartment in Historic Chestertown](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information): Located in Chestertown, 18.5 mi/29.8 km from Chester. Includes a private pool, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. ### What will the weather be like during my trip to Chester? > Though weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Chester. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches. ### What should I see in Chester? > Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Chesapeake Bay Environmental Center. In the larger area, you'll find Matapeake State Park and Love Point State Park. ### What's the best way to get to and around Chester? > Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) away from the heart of the city. You can also search for flights into Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away. 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