Title: Chestertown Apartment Rentals from CA $172 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Apartment Rentals in Chestertown - ![](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 [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7215&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 two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown 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) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.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) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Chestertown [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) 9.6/10 Exceptional (108) "We had a lovely visit. It was nice and quiet and parking was perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne D. CA $136 CA $218 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w503h683x261y0-8de504dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w451h683x287y0-42a2db1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w584h683x220y0-d805a755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Millington [](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information) 9.6/10 Exceptional (19) "So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia C. CA $93 CA $172 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0e2deec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0fab08c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) 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 $284 CA $568 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/6b42c6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/05e68e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/43e61d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/53cce118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Worton [](https://www.expedia.ca/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information) 10/10 Exceptional (25) "Quiet and relaxing spot right on the water" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer W. CA $240 CA $427 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/ccc91804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/8b45f44e.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/117000000/116070000/116070000/116069925/c897d865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116070000/116070000/116069925/a32de752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Greektown [](https://www.expedia.ca/Baltimore-Hotels-Cozy-2-Bedroom-Apartment-In-Welcoming-Baltimore-With-WiFi.h116069925.Hotel-Information) 9.6/10 Exceptional (8) "The house was clean and the beds were comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen B. CA $185 CA $311 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Baltimore-Hotels-Cozy-2-Bedroom-Apartment-In-Welcoming-Baltimore-With-WiFi.h116069925.Hotel-Information) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121420000/121417100/121417063/ddacbdd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121420000/121417100/121417063/785ba60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121420000/121417100/121417063/6664b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121420000/121417100/121417063/4fe9d60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Nottingham [](https://www.expedia.ca/Baltimore-Hotels-Close-To-Hospital-White-Marsh-Rosedale-Townhome.h121417063.Hotel-Information) CA $261 CA $732 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Baltimore-Hotels-Close-To-Hospital-White-Marsh-Rosedale-Townhome.h121417063.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109510000/109509200/109509193/e748b25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109510000/109509200/109509193/7d13e53c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109510000/109509200/109509193/5ee71d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109510000/109509200/109509193/06f0fce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Ellwood Park/Monument [](https://www.expedia.ca/Baltimore-Hotels-1-Bedroom-Apartment-Just-8-Minutes-Drive-To-Oriole-Park-At-Camden-Yards.h109509193.Hotel-Information) CA $136 CA $452 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Baltimore-Hotels-1-Bedroom-Apartment-Just-8-Minutes-Drive-To-Oriole-Park-At-Camden-Yards.h109509193.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/7d32385a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/a8b6b33a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/b07ecc79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/77000000/76590000/76586000/76585906/81cde5a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Historic District [](https://www.expedia.ca/Annapolis-Hotels-Spacious-Downtown-Getaway-Across-From-US-Naval-Academy.h76585906.Hotel-Information) 9.6/10 Exceptional (27) "Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) betsy b. CA $233 CA $433 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Annapolis-Hotels-Spacious-Downtown-Getaway-Across-From-US-Naval-Academy.h76585906.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/05703878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/528b087a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/985e9e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/bec6a7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Historic District [](https://www.expedia.ca/Annapolis-Hotels-Charming-Downtown-3rd-Floor-1-Bedroom-Apt.h76579660.Hotel-Information) 9.8/10 Exceptional (20) "We had a great time staying that this home. It was a perfect stay for my wife and I." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric S. CA $219 CA $397 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Annapolis-Hotels-Charming-Downtown-3rd-Floor-1-Bedroom-Apt.h76579660.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=2026-01-17&endDate=2026-01-18®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FChestertown-Apartments.d7215-aaApartments.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Apartments.d7215-aaApartments.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Everything was wonderful at this hotel except the breakfast. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "Check in was smooth, room was spacious and clean, free parking and breakfast included. The location near the highway was good for us no waist time for driving travellers " [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 10/10 Excellent "The cleaniness, the staff and service were all top notch. Would definitely stay again and recommend to others" [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Courteous" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "Nice and clean room , very well maintained. I’ll stay here again " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.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 "Lovely historical hotel in the heart of downtown Annapolis. Very friendly staff " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg) ### Fairfield Inn & Suites by Marriott Middletown 10/10 Excellent "Overall great stay. Will come here again" [](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Room had a strange old smell and the beds weere not clean at all " [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Staff is friendly, efficient and kind. Also when I had an issue with the room, it was fixed promptly and staff was very apologetic and again just overall friendly and wonderful." [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## Find out more about Chestertown ## Chestertown Apartments information | Number of reviews | 269 | | ----------------- | ------------- | | Accommodation | 80 Apartments | | Lowest Price | CA $172 | | Highest Price | CA $732 | ## Frequently asked questions ### What's it like to stay at an apartment in Chestertown? ### Why should you consider apartments instead of traditional hotels? ### What's the top apartment for my stay in Chestertown? ### How many apartments can I expect to find in Chestertown? ### What can I expect from the weather during my trip to Chestertown? ### What should I see and do in Chestertown? ### What's the best way to get to and around Chestertown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Best Western Hotels in Aberdeen Proving Ground ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels-Best-Western.0-0-d553248634999428212--bBestWestern.Travel-Guide-Filter-Hotels) - 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