Title: Book the Best ROMANTIC Hotels in Chestertown, MD from CA $209 - Chestertown Romantic Getaways | 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) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find Romantic Hotels in Chestertown, MD from CA $209 ![](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 Romantic Hotels Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-11&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-11&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Romantic Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1846) "Perfect location…terrific staff…spacious room with a king sized bed! " CA $146 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (114) "Great INN super nice staff" CA $265 CA $347 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (421) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " CA $272 CA $337 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/2dabe54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 (Rodgers) | Bathroom](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/w491h206x3y3-e2361b9b.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 Havre De Grace 9.4/10 Exceptional (519) "Been to the Vandiver many times and are always pleasantly pleased." CA $194 CA $218 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/4cc768f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/44c7f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Baltimore Downtown/McHenry Row Locust Point 9.0/10 Wonderful (673) "Great location " CA $178 CA $209 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/1976e6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/42213387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/03fed2cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/2624f48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel Annapolis 9.8/10 Exceptional (26) "Very friendly staff!" CA $287 CA $328 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/65ec141b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/44aeb3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/0d7cc499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/2c031a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Fells Point Gem / In The Heart of Fells Point Fells Point 9.8/10 Exceptional (197) "Great place close to eveything" CA $87 CA $285 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-CitySide-Tons-Better-Than-A-Hotel.h19007969.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 19.90 per person)](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/b358be96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/d1715c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/e343ffe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel Fells Point 9.2/10 Wonderful (737) "Great location and very friendly staff! " CA $225 CA $293 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking, Balcony](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/af281015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/fb8e8cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection Historic District 8.8/10 Excellent (870) "Beautiful location, big rooms " CA $285 CA $325 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/3fe6d96d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/2ec17b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/62f27275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/0085cedc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs Canton 9.8/10 Exceptional (64) "Cute and quiet neighborhood with a beautiful view of the park. The host made it a stress free stay with great tips." CA $205 CA $400 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Baltimore-Hotels-Luxury-Parkfront-Haven-With-Hot-Tub-Beloved-By-Families-Their-Dogs.h23927080.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=2025-10-24&endDate=2025-10-25®ionId=7215&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](//images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Very nice and clean" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Excellent stay but I never received my wine " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Sagamore Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Sagamore Pendry Baltimore 10/10 Excellent "Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!" [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Easy access, dmooth check in, felt safe parking, close to port. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](//images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Clean and quiet " [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chestertown? > Are you looking for a romantic vacation? You might consider checking out some of the nearby sights and attractions such as Historical Society of Kent County Maryland, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Chestertown? > If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches. ### What is there to do in Chestertown? > There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Chestertown has to offer. A visit to Historical Society of Kent County Maryland, Rolphs Wharf Marina, or Garfield Center for the Arts at the Prince Theater might be just the ticket when you're checking out the sights. ### What's the best way to get to Chestertown and around town during my romantic getaway? > These transportation options in Chestertown might help your romantic getaway go off without a hitch: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), which is the closest major airport, located 20.3 mi (32.7 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights. ## 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 Romantic Hotels in Chestertown on Expedia.com](https://www.expedia.com/Chestertown-Hotels-Romantic-Hotel.0-0-d7215-tRomanticHotel.Travel-Guide-Filter-Hotels)