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 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 two weeks [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 one month [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=LODGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-15&endDate=2026-05-17&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) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/c765d8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.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) ### 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 17 - Mar 18 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=2026-03-30&endDate=2026-03-31®ionId=7215&adults=2&lodging=LODGE&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.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 & 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 "Room was clean and in great condition. " [](https://expedia.com/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![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 "Internet was fine. No pets n/a" [](https://expedia.com/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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 6/10 Okay "The room that me and my family stayed in was “ PERFECT”! I even left a “ Thank you” note and a tip. The pool area was ok. I do Have one complaint. The receptionist at the front desk, Asian women was very NONCHALANT, SNOBBY and ARROGANT! As we know that the rooms there are not cheap, so I would have loved to experience professionalism from the receptionist when checking in. Therefore, I WILL NOT be coming back to that hotel again!" [](https://expedia.com/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.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 4/10 Poor "I cut my foot on a broken chair in the room. I went down to the front desk to ask for if they had a bandaide and something to clean the cut with. When I arrived at the front desk the attendant was watching something on her phone and didnt acknowledge me until I spoke up. When I asked for if they had a first aid kit she went to check and said that it was empty and all they had was gauze, no bandaid, no medical tape, no cleansing wipes no nothing. My toes was bleeding so much that I ended up wrapping it in gauze and using office tape from the front desk. The attendant didn't apologize, ask to swap out the broken chair or offer any kind of accommodations to rectify the situation. I left feeling that she didn't care and she just wanted to get back to whatever she was watching on her phone. " [](https://expedia.com/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open." [](https://expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg) ### Hampton Inn Baltimore Bayview Campus 10/10 Excellent "Clean room" [](https://expedia.com/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56_y.jpg) ### Best Western Kent Narrows Inn 4/10 Poor "The first room had not been cleaned... The second room's heater did not work. We finally got into a decent room on the third try. The pool was murky. I didn't even let my kids go in the hot tub because it smelled so weird. The sauna was luke warm. The breakfast was good, and the staff were trying hard. Overall, it was functional but a little run-down and understaffed. " [](https://expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/c6a165a6_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 8/10 Good "Room was clean." [](https://expedia.com/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![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) ## 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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