Title: Best Chestertown, MD Lodge Rentals from $137 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown lodges ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/021b413d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/c765d8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing [](https://www.expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) Chestertown 7.8/10 Good (77 reviews) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania $124 nightly $137 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.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.com/Hotel-Search?startDate=2026-03-28&endDate=2026-03-29®ionId=7215&adults=2&lodging=LODGE&sort=RECOMMENDED&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.com/deals?rfrr=AA_SPRING_PROMO_7215) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Lodges.d7215-aaLodges.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Lodges.d7215-aaLodges.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Room and all surrounding areas were very clean. The staff was so kind and so friendly. It is in an amazing location and some very good choices for food right in the shopping plaza. " [](https://expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94_y.jpg) ### Fairfield Inn & Suites by Marriott Middletown 6/10 Okay "Wasn’t pleased." [](https://expedia.com/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Country Inn & Suites by Radisson, Baltimore North, MD](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16_y.jpg) ### Country Inn & Suites by Radisson, Baltimore North, MD 10/10 Excellent "Clean quiet " [](https://expedia.com/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Everything was clean and near" [](https://expedia.com/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg) ### Historic Inns of Annapolis 8/10 Good "The elevator was not working the entire time." [](https://expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/6e9faa08_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent " Clean, comfortable, good location." [](https://expedia.com/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/9b37b4b6_y.jpg) ### Holiday Inn Express White Marsh by IHG 8/10 Good "The food was better than continental " [](https://expedia.com/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 8/10 Good "The hotel has almost everything that we needed. No airport transport. There is a service to get to the cruise port, but a high price to go a very short distance. " [](https://expedia.com/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Very nice" [](https://expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ## Find out more about Chestertown ## Chestertown Lodges information | Number of reviews | 77 | | ----------------- | -------- | | Accommodation | 1 Lodges | | Lowest Price | $137 | | Highest Price | $137 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Washington College ](https://www.expedia.com/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels near River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) - 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[Business Hotels in Rock Hall ](https://www.expedia.com/Rock-Hall-Hotels-Business-Hotel.0-0-d177447-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels near The Mainstay ](https://www.expedia.com/The-Mainstay-Hotels.0-l553248621532662296-0.Travel-Guide-Filter-Hotels) - [Hotels near Betterton Beach ](https://www.expedia.com/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - [Hotels near Rock Hall Harbor ](https://www.expedia.com/Rock-Hall-Harbor-Hotels.0-l553248621561173703-0.Travel-Guide-Filter-Hotels) - [Hotels near Waterman’s Museum ](https://www.expedia.com/Watermans-Museum-Hotels.0-l673471647360921600-0.Travel-Guide-Filter-Hotels) - [Flights to Worton ](https://www.expedia.com/Cheap-Flights-To-Worton.d3000440948.Travel-Guide-Flights) - [Flights from Pomona ](https://www.expedia.com/lp/flights/553248635976007038/flights-from-pomona) - [Flights to Church Hill ](https://www.expedia.com/Cheap-Flights-To-Church-Hill.d6359186.Travel-Guide-Flights) - [Flights from Kennedyville ](https://www.expedia.com/lp/flights/3000440679/flights-from-kennedyville) - [Flights to Betterton ](https://www.expedia.com/Cheap-Flights-To-Betterton.d3000440429.Travel-Guide-Flights) - [Flights to Rock Hall ](https://www.expedia.com/Cheap-Flights-To-Rock-Hall.d177447.Travel-Guide-Flights) - [Washington College ](https://www.expedia.com/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction) - [River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Chestertown.d553248621532662298.Vacation-Attraction) - [Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction) - [Wilmer Park ](https://www.expedia.com/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [Rolphs Wharf Marina ](https://www.expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) - 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[Rock Hall Vacation Rentals ](https://www.expedia.com/Rock-Hall-Vacation-Rentals.d177447.Travel-Guide-VacationRentals)