Title: Book the Best BEACH RESORTS in Chestertown, MD - Chestertown Hotels on the Beach| 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) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 availability on Chestertown Beach Hotel Tonight [Feb 20 - Feb 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-20&endDate=2026-02-21&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [Feb 21 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-21&endDate=2026-02-22&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Our top choices for Chestertown beach hotels ![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) ![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) ![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) ### The Lodge at Great Oak Landing [](https://www.expedia.ca/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 CA $148 CA $169 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/48ed0abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2547x3y4-94e4330e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/7074520f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/f0086565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Baltimore / Aberdeen, MD [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) Aberdeen 8.8/10 Excellent (349 reviews) "Awesome staff, very clean, great pool Awesome breakfast!!! All good things" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patty CA $128 CA $143 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/c9b926ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) Historic District 10/10 Exceptional (74 reviews) "Welcoming host, great location and easy parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris B. CA $213 CA $490 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/e818c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) Historic District 9.4/10 Exceptional (87 reviews) "The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $249 CA $283 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/742476e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/75e8b664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/cea35751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/d24d6107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG [](https://www.expedia.ca/Edgewood-Hotels-Holiday-Inn-Express-Edgewood-Aberdeen-Bel-Air.h281612.Hotel-Information) Edgewood 9.0/10 Wonderful (573 reviews) "A solid place to stay in the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald CA $105 CA $118 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Edgewood-Hotels-Holiday-Inn-Express-Edgewood-Aberdeen-Bel-Air.h281612.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/e8d235bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/e831c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/2fa15be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/655332ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Retreat with Private Dock and Beach [](https://www.expedia.ca/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information) Worton 10/10 Exceptional (25 reviews) "The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie S. CA $240 CA $431 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Worton-Hotels-Cozy-Waterfront-Retreat-With-Private-Dock-And-BeachSleeps-4-Studio-1-Bath.h103180013.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/5bf9cecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Tydings)](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/727c3c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/052f9ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (O'Neill) | Living area](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) Havre De Grace 9.4/10 Exceptional (535 reviews) "a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dieter [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/w800h599x0y1-14614b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/c3a4247f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/269a9c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/e058846a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5-bedroom vacation home 5 minutes from historic Charlestown [](https://www.expedia.ca/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information) Perryville 9.8/10 Exceptional (147 reviews) "Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary D. CA $354 CA $724 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/9d2ec177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/c8800660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/a4e1c9eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95980000/95979600/95979564/8af0ae73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hobbit House one of a kind home [](https://www.expedia.ca/Bel-Air-Hotels-Hobbit-House-One-Of-A-Kind-Home.h95979564.Hotel-Information) Bel Air 10/10 Exceptional (9 reviews) "We had a great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney H. CA $128 CA $383 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Bel-Air-Hotels-Hobbit-House-One-Of-A-Kind-Home.h95979564.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower)](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/b92b6259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/678460fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a7c447e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) Aberdeen 9.0/10 Wonderful (1,005 reviews) "Everything was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) juan CA $113 CA $126 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.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=2026-03-06&endDate=2026-03-07®ionId=7215&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at beach hotels in Chestertown Pool Ocean view Breakfast included 4 stars 5 stars ![](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.ca/deals?rfrr=AFFINITY_SPRING_PROMO_7215) ## Find out more about Chestertown ### Chestertown and its attractions for beach lovers Located just a short drive from the serene beaches of the Chesapeake Bay, Chestertown, Maryland, offers a delightful blend of charm and coastal adventure for families seeking quality experiences. Start your exploration at Wilmer Park, where the scenic waterfront beckons with picnic spots and walking trails, perfect for a leisurely afternoon with the family. Just a stone’s throw away, the Chestertown Marina invites visitors to enjoy kayaking or paddleboarding, providing a unique perspective of the town from the water. Art enthusiasts can visit the nearby Kent County Arts Council, which showcases local talents and often hosts family-friendly workshops. For a taste of local history, the Custom House Museum offers engaging exhibits that delve into the town's rich maritime heritage. After a day of exploration, families can unwind at hotels along the waterfront, where attentive service and comfortable accommodations ensure a relaxing stay. Opt for a hotel with easy access to the beach, allowing for spontaneous beach outings, while also enjoying the quaint atmosphere of Chestertown’s historic streets, lined with boutique shops and delightful eateries. ### Find the best beach hotels and resorts in Chestertown For those seeking a beach getaway in Chestertown, Maryland, these hotels offer the perfect blend of comfort and coastal charm. Enjoy sun-soaked days and stunning views at these delightful properties. [**The Lodge at Great Oak Landing**](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) - **Why it's great for the ultimate beach vacation spot:** The Lodge at Great Oak Landing is an ideal retreat for beach lovers, a solid guest review rating of 8.2\. Guests can enjoy direct access to a private sand beach, perfect for sunbathing and relaxation. With a variety of beach amenities including sun loungers, a waterfront location, and volleyball courts, it promises a fun-filled coastal experience. - **Other amenities:** This hotel features a shared pool with sun loungers and umbrellas, ensuring ample relaxation options. Active guests can take advantage of the 24-hour fitness facilities, while families will appreciate the playground. Additional conveniences include self-parking options, a mini-refrigerator in rooms, and stunning marina views to enjoy during your stay. - **Nearby attractions:** Kinnairds Point Drive - 19.6 km, Still Pond Station Park - 24.5 km ## Top Chestertown Hotel Reviews ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Polite and kind hotel manager" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travelers who love the beach? ### What's the best hotel for a beach vacation in Chestertown? ### When's the best time for a beach vacation in Chestertown? ### What is there to see and do around Chestertown? ### What's the best way to get to my beach hotel in Chestertown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Belcamp ](https://www.expedia.ca/Belcamp-Hotels-Cheap-Hotels.0-0-d602125-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Belcamp ](https://www.expedia.ca/Belcamp-Hotels-Family-Hotel.0-0-d602125-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Apartments in Betterton ](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach ](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - [Cottages in Betterton ](https://www.expedia.ca/Betterton-Cottages.d3000440429-aaCottages.Travel-Guide-Accommodation) - [Betterton Hotels ](https://www.expedia.ca/Betterton-Hotels.d3000440429.Travel-Guide-Hotels) - [Resorts in Betterton ](https://www.expedia.ca/Betterton-Resort-Hotels.d3000440429-aaResortHotels.Travel-Guide-Accommodation) - [Boutique Hotels in Bowleys Quarters ](https://www.expedia.ca/Bowleys-Quarters-Middle-River-Hotels-Boutique-Hotel.0-n553248635975874512-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Farmstay in Centreville ](https://www.expedia.ca/Centreville-Agritourism.d88125-aaAgritourism.Travel-Guide-Accommodation) - [Chalets in Centreville ](https://www.expedia.ca/Centreville-Chalets.d88125-aaChalets.Travel-Guide-Accommodation) - [Boutique Hotels in Centreville ](https://www.expedia.ca/Centreville-Hotels-Boutique-Hotel.0-0-d88125-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Centreville Hotels ](https://www.expedia.ca/Centreville-Hotels.d88125.Travel-Guide-Hotels) - [Inns in Centreville ](https://www.expedia.ca/Centreville-Inns.d88125-aaInns.Travel-Guide-Accommodation) - [Cheap Hotels in Church Hill ](https://www.expedia.ca/Church-Hill-Hotels-Cheap-Hotels.0-0-d6359186-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Church Hill ](https://www.expedia.ca/Church-Hill-Hotels-Hotels-With-Hot-Tubs.0-0-d6359186-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Church Hill Hotels ](https://www.expedia.ca/Church-Hill-Hotels.d6359186.Travel-Guide-Hotels) - [Inns in Church Hill ](https://www.expedia.ca/Church-Hill-Inns.d6359186-aaInns.Travel-Guide-Accommodation) - [Historic Hotels in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Historic-Hotel.0-0-d222-tHistoricHotel.Hotel-Filter-Destinations) - [Hotels with Early Check-in in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Hotel-With-Early-Check-In.0-0-d222-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with Free Airport Shuttle in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Hotels-With-Free-Airport-Shuttle.0-0-d222-tHotelswithFreeAirportShuttle.Hotel-Filter-Destinations) - [Hotels with Hot Tubs in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Hotels-With-Hot-Tubs.0-0-d222-tHotelsWithHotTubs.Hotel-Filter-Destinations) - [Mountain Hotels in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Mountain-Hotels.0-0-d222-tMountainHotels.Hotel-Filter-Destinations) - [Oceanfront Hotels in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Oceanfront-Hotels.0-0-d222-tOceanfrontHotels.Hotel-Filter-Destinations) - [Winery Hotels in Maryland ](https://www.expedia.ca/Destinations-In-Maryland-Winery-Hotel.0-0-d222-tWineryHotel.Hotel-Filter-Destinations) - [Earleville Hotels ](https://www.expedia.ca/Earleville-Hotels.d6359189.Travel-Guide-Hotels) - [Hotels near Eastern Neck National Wildlife Refuge ](https://www.expedia.ca/Eastern-Neck-National-Wildlife-Refuge-Hotels.0-l553248635974660968-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Edgewood ](https://www.expedia.ca/Edgewood-Hotels-Cheap-Hotels.0-0-d10362-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Edgewood ](https://www.expedia.ca/Edgewood-Hotels-Family-Hotel.0-0-d10362-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Edgewood ](https://www.expedia.ca/Edgewood-Hotels-Hotels-With-Free-Breakfast.0-0-d10362-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Edgewood ](https://www.expedia.ca/Edgewood-Hotels-Luxury-Hotel.0-0-d10362-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Edgewood ](https://www.expedia.ca/Edgewood-Hotels-Romantic-Hotel.0-0-d10362-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Edgewood ](https://www.expedia.ca/Edgewood-Hotels-Winery-Hotel.0-0-d10362-tWineryHotel.Travel-Guide-Filter-Hotels) - [B&B in Galena ](https://www.expedia.ca/Galena-Bed-And-Breakfast.d106992-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels with Hot Tubs in Galena ](https://www.expedia.ca/Galena-Hotels-Hotels-With-Hot-Tubs.0-0-d106992-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Galena ](https://www.expedia.ca/Galena-Hotels-Romantic-Hotel.0-0-d106992-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Galena Hotels ](https://www.expedia.ca/Galena-Hotels.d106992.Travel-Guide-Hotels) - [Lodges in Galena ](https://www.expedia.ca/Galena-Lodges.d106992-aaLodges.Travel-Guide-Accommodation) - [Motels in Galena ](https://www.expedia.ca/Galena-Motels.d106992-aaMotels.Travel-Guide-Accommodation) - [Resorts in Galena ](https://www.expedia.ca/Galena-Resort-Hotels.d106992-aaResortHotels.Travel-Guide-Accommodation) - [Independent Hotels in Georgetown ](https://www.expedia.ca/Georgetown-Hotels-Independent.0-0-d553248635975874069--bIndependent.Travel-Guide-Filter-Hotels) - [Rv Parks in Georgetown ](https://www.expedia.ca/Georgetown-RV-Parks.d553248635975874069-aaRVParks.Travel-Guide-Accommodation) - [Villas in Georgetown ](https://www.expedia.ca/Georgetown-Villas.d553248635975874069-aaVillas.Travel-Guide-Accommodation) - [Cheap Hotels in Grasonville ](https://www.expedia.ca/Grasonville-Hotels-Cheap-Hotels.0-0-d7382-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Grasonville ](https://www.expedia.ca/Grasonville-Hotels-Luxury-Hotel.0-0-d7382-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Grasonville ](https://www.expedia.ca/Grasonville-Hotels-Oceanfront-Hotels.0-0-d7382-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Guest Houses in Great Oak Landing ](https://www.expedia.ca/Great-Oak-Landing-Guest-Houses.d3000045661-aaGuestHouses.Travel-Guide-Accommodation) - [Great Oak Landing Hotels ](https://www.expedia.ca/Great-Oak-Landing-Hotels.d3000045661.Travel-Guide-Hotels) - [Rv Parks in Great Oak Landing ](https://www.expedia.ca/Great-Oak-Landing-RV-Parks.d3000045661-aaRVParks.Travel-Guide-Accommodation) - [Lodges in Kennedyville ](https://www.expedia.ca/Kennedyville-Lodges.d3000440679-aaLodges.Travel-Guide-Accommodation) - [Hotels with a Pool in Kent Narrows ](https://www.expedia.ca/Kent-Narrows-Hotels-Hotel-With-Pool.0-0-d553248635077720315-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Kent Narrows ](https://www.expedia.ca/Kent-Narrows-Hotels-Hotels-With-Indoor-Pool.0-0-d553248635077720315-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Lake Hotels in Kent Narrows ](https://www.expedia.ca/Kent-Narrows-Hotels-Lake-Hotels.0-0-d553248635077720315-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Kent Narrows ](https://www.expedia.ca/Kent-Narrows-Hotels-Luxury-Hotel.0-0-d553248635077720315-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [B&B in Massey ](https://www.expedia.ca/Massey-Bed-And-Breakfast.d3000440702-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Massey Hotels ](https://www.expedia.ca/Massey-Hotels.d3000440702.Travel-Guide-Hotels) - [Lodges in Massey ](https://www.expedia.ca/Massey-Lodges.d3000440702-aaLodges.Travel-Guide-Accommodation) - [Motels in Massey ](https://www.expedia.ca/Massey-Motels.d3000440702-aaMotels.Travel-Guide-Accommodation) - [Millington Hotels ](https://www.expedia.ca/Millington-Hotels.d3000440734.Travel-Guide-Hotels) - [Luxury Hotels in Perryman ](https://www.expedia.ca/Perryman-Hotels-Luxury-Hotel.0-0-d3000347960-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pomona Hotels ](https://www.expedia.ca/Pomona-Hotels.d553248635976007038.Travel-Guide-Hotels) - [Vacation Homes in Pomona ](https://www.expedia.ca/Pomona-Private-Vacation-Homes.d553248635976007038-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Queen Anne's County ](https://www.expedia.ca/Queen-Annes-County-Apartments.d553248635976431659-aaApartments.Travel-Guide-Accommodation) - [B&B in Queen Anne's County ](https://www.expedia.ca/Queen-Annes-County-Bed-And-Breakfast.d553248635976431659-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Queenstown ](https://www.expedia.ca/Queenstown-Hotels-Boutique-Hotel.0-0-d56094-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Queenstown ](https://www.expedia.ca/Queenstown-Hotels-Hotel-With-Pool.0-0-d56094-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Queenstown ](https://www.expedia.ca/Queenstown-Hotels-Luxury-Hotel.0-0-d56094-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Queenstown ](https://www.expedia.ca/Queenstown-Hotels-Spa-Hotel.0-0-d56094-tSpaHotel.Travel-Guide-Filter-Hotels) - [B&B in Rock Hall ](https://www.expedia.ca/Rock-Hall-Bed-And-Breakfast.d177447-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Rock Hall Harbor ](https://www.expedia.ca/Rock-Hall-Harbor-Hotels.0-l553248621561173703-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Rock Hall ](https://www.expedia.ca/Rock-Hall-Hotels-Beach-Hotel.0-0-d177447-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Rock Hall ](https://www.expedia.ca/Rock-Hall-Hotels-Cheap-Hotels.0-0-d177447-tCheapHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Rock Hall ](https://www.expedia.ca/Rock-Hall-Hotels-Oceanfront-Hotels.0-0-d177447-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Rock Hall Hotels ](https://www.expedia.ca/Rock-Hall-Hotels.d177447.Travel-Guide-Hotels) - [Motels in Rock Hall ](https://www.expedia.ca/Rock-Hall-Motels.d177447-aaMotels.Travel-Guide-Accommodation) - [Still Pond Hotels ](https://www.expedia.ca/Still-Pond-Hotels.d3000347996.Travel-Guide-Hotels) - [Lodges in Still Pond ](https://www.expedia.ca/Still-Pond-Lodges.d3000347996-aaLodges.Travel-Guide-Accommodation) - [Villas in Still Pond ](https://www.expedia.ca/Still-Pond-Villas.d3000347996-aaVillas.Travel-Guide-Accommodation) - [Farmstay in Tolchester Beach ](https://www.expedia.ca/Tolchester-Beach-Agritourism.d553248635975848245-aaAgritourism.Travel-Guide-Accommodation) - [Hotels near Washington College ](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Washington ](https://www.expedia.ca/Washington-Hotels-Couples-Resorts-Hotels.0-0-d178318-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Washington ](https://www.expedia.ca/Washington-Hotels-Green-Sustainable.0-0-d178318-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Washington ](https://www.expedia.ca/Washington-Hotels-Hotels-With-A-Lazy-River.0-0-d178318-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Washington ](https://www.expedia.ca/Washington-Hotels-Hotels-With-Childcare.0-0-d178318-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Washington ](https://www.expedia.ca/Washington-Hotels-Hotels-With-Tennis-Courts.0-0-d178318-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Lake Hotels in Washington ](https://www.expedia.ca/Washington-Hotels-Lake-Hotels.0-0-d178318-tLakeHotels.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Washington ](https://www.expedia.ca/Washington-Hotels-Shopping-Hotel.0-0-d178318-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Washington ](https://www.expedia.ca/Washington-Hotels-Ski-Hotel.0-0-d178318-tSkiHotel.Travel-Guide-Filter-Hotels) - [Worton Hotels ](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels) - [Luxury Hotels in Wye Mills ](https://www.expedia.ca/Wye-Mills-Hotels-Luxury-Hotel.0-0-d6359185-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Flights from Kennedyville ](https://www.expedia.ca/lp/flights/3000440679/flights-from-kennedyville) - [Flights from Massey ](https://www.expedia.ca/lp/flights/3000440702/flights-from-massey) - [Flights from Barclay ](https://www.expedia.ca/lp/flights/553248634998993874/flights-from-barclay) - [Flights from Centreville ](https://www.expedia.ca/lp/flights/88125/flights-from-centreville) - [Historical Society of Kent County Maryland ](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Mount Harmon Plantation ](https://www.expedia.ca/Mount-Harmon-Plantation-Earleville.d553248621561879694.Vacation-Attraction) - [Wilmer Park ](https://www.expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [Car rental Centreville ](https://www.expedia.ca/Car-Rentals-In-Centreville.d88125.Car-Rental-Guide) - [Centreville Vacation Rentals ](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals) - [Book Beach Hotel in Chestertown on Expedia.com ](https://www.expedia.com/Chestertown-Hotels-Beach-Hotel.0-0-d7215-tBeachHotel.Travel-Guide-Filter-Hotels)