Title: Book the Best HISTORIC Hotels in Chestertown in 2025 | 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 Historic Hotels in Chestertown, MD from CA $167 - ![](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 Historic Hotels Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Historic 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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1875) "Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $145 CA $214 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/w1857h2500x0y0-ac5cefb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/6c83d519.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) ### Flag House Inn Historic District 9.4/10 Exceptional (79) "Great place to stay when visiting Annapolis." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $146 CA $167 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/d1715c4d.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/69872362.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 (747) "Beautiful location and a great stay. Eric at the front desk was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) dena CA $189 CA $250 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/226d6f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/8a68c06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/76c1b6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Fells Point Gem / Private Courtyard Patio Fells Point 9.6/10 Exceptional (89) "Lenny’s apartment was the perfect base for our Baltimore visit! It’s just a short walk to the water where there are shops, restaurants and bars. The space is cozy, has everything you need to make meals and was very clean. Lenny was quick to respond to questions and was very accommodating. Thanks for a great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen S. CA $87 CA $291 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.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) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/2624f48e.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) ![Presidential Single Room, 1 King Bed, Bathtub, Harbour View](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/15680a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel Annapolis 9.8/10 Exceptional (28) "Very friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard [](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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/w799h599x1y1-de620c30.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 (198) "Awesome alternative to a hotel, perfect location, walking distance to all Fells Point attractions, bars and restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue CA $87 CA $291 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-CitySide-Tons-Better-Than-A-Hotel.h19007969.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) ![Exterior](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/62f27275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/366316a3.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) ### Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs Canton 9.8/10 Exceptional (65) "This was the best VRBO experience we've ever had. The property was exactly as described, the location was fantastic, and the rental property was the best stocked property we've ever experienced. Absolutely perfect?" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bill H. CA $249 CA $460 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Baltimore-Hotels-Luxury-Parkfront-Haven-With-Hot-Tub-Beloved-By-Families-Their-Dogs.h23927080.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) ![Outdoor dining](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/ba6b073a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/5acb80c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis Historic District 10/10 Exceptional (71) "Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheldon E. CA $168 CA $438 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/a8bf1b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, City View](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/eaea568e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/8d2066be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel Historic District 10/10 Exceptional (2) "Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels." ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Jo CA $451 CA $515 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/5f5b0904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/2f9f691d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/1b3fe24b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/e6912d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Cottages- 2 Quaint Waterfront Retreats Pasadena 9.6/10 Exceptional (22) "Excellent Property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Buu T. CA $504 CA $931 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.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=2025-11-17&endDate=2025-11-18®ionId=7215&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](//images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "This hotel was great. Clean rooms, comfortable beds and friendly staff." [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.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 "The location is excellent. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Friendly and welcoming valet and front desk. Beautiful and clean rooms. Disappointed no restaurant but understand. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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 "We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Garner Hotel Glen Burnie BWI Airport Area by IHG](//images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg) ### Garner Hotel Glen Burnie BWI Airport Area by IHG 10/10 Excellent "Will definitely be back again 🙌" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "Love it always " [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![Red Roof Inn & Suites Chestertown](//images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "Well received by front desk attendant. Clean room! " [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ## Frequently asked questions ### What can I expect on my historical trip to Chestertown? > You'll probably want to seek out the places with historical relevance during your vacation in Chestertown. You can also enjoy the many sights including the sporting events and university setting ### How many historical hotels will I find in Chestertown? > Chestertown is home to 37 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from. ### What are the must-see historical places and other sights to visit in Chestertown? > Chestertown is notable for landmarks like Historical Society of Kent County Maryland. The picturesque setting of Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater. ### What is a historic hotel like in Chestertown? > When you choose a historic hotel, you'll stay someplace that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel as long as it has special significance. Traditional architecture and period features can be admired within the guestrooms or public spaces of these historic hotels in Chestertown, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. but overall the terms are quite similar. The architecture and actual building of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value and how it influenced the community. ### Do historic hotels in Chestertown have modern facilities? > Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found at a contemporary hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Chestertown, you won't find yourself staying at a place that's uncomfortable or rundown. ## 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 Historic Hotels in Chestertown on Expedia.com](https://www.expedia.com/Chestertown-Hotels-Historic-Hotel.0-0-d7215-tHistoricHotel.Travel-Guide-Filter-Hotels)