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 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-01&endDate=2026-05-03&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) ![Reception](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/021b413d.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) ![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=2026-03-22&endDate=2026-03-23®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 ![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 10/10 Excellent "The room was very good, the breakfast was delicious and the choices we had were great. We loved the new coffee machine. Enjoyed our stay and would stay again in the future." [](https://expedia.com/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/38012dd1_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "Clean room, nice staff and great breakfast " [](https://expedia.com/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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 "Most area were very good. Staff was friendly & accommodating. Some areas were new/updated (lobby, cafe, gym were great). Rooms were a little small; lamp shades dusty; bed should face the tv; bedroom furniture a little worn; did not get housekeeping on Friday; HVAC blowing too hard/noisy so room temp not comfortable; parking was a plus/great; location was good… on the whole, a good experience " [](https://expedia.com/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 8/10 Good "Our stay was pretty good. The free breakfast was really good, the pool area was nice and the room was pretty nice as well. No complaints " [](https://expedia.com/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information) ![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg) ### Comfort Inn & Suites Aberdeen near APG 6/10 Okay "For a night to rest our heads, this stay was ok. While the floors were sticky and the hot breakfast was cold, the bed was comfortable enough for us the sleep like a rock. " [](https://expedia.com/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.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 "Excellent " [](https://expedia.com/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Clean and courteous staff. " [](https://expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/5d79a398_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Clean room and helpful staff" [](https://expedia.com/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.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 8/10 Good "The staff was very nice and helpful. However, the towels and sheets were dirty or dingy. My sheets were dirty. The pillow cases had pills from wear. They definitely need to replace the sheets and towels due to wear and tear. Breakfast was good!" [](https://expedia.com/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.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) - [Hotels near Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) - 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