Title: Book the Best Hotels with POOL 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) ![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) # Find Hotels with a Pool in Chestertown, MD from CA $106 - ![](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 Hotels with a Pool Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Hotels with a Pool ![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.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 Chestertown 8.0/10 Very good (75) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania CA $138 CA $158 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/4dc8f4ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (848) "The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Santa CA $143 CA $158 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown 9.6/10 Exceptional (106) "Amazing and neat and very private " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander M. CA $138 CA $222 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/791afcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown Middletown 9.2/10 Wonderful (305) "Great overall experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clement CA $151 CA $168 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Edgewood/Aberdeen-South Edgewood 9.4/10 Exceptional (1005) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dena CA $114 CA $128 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/0ab02da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/6d549ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Baltimore/Aberdeen Aberdeen 9.0/10 Wonderful (591) "Wonderful room and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caren CA $126 CA $142 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) ![Indoor pool, open 5 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/b307a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina Grasonville 9.0/10 Wonderful (1000) "Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $142 CA $158 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/600/507/6aed5619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/250ceaaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/600/507/5c9bcbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/e2e5d244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Aberdeen by IHG Aberdeen 8.6/10 Excellent (425) "Kid friendly for sure! The room and hotel is clean and comfy, no complaints! Chlorine smell a bit strong in pool area but it didn’t bother me. We missed breakfast so not sure about that but everything else was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabrielle CA $160 CA $179 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Aberdeen-Hotels-Holiday-Inn-Express-Aberdeen.h507.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/bcb2d6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/9a72fb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/7daf57ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/e5cd056f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Edgewood Aberdeen Aberdeen 9.0/10 Wonderful (90) "Breakfast was good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Romelle CA $141 CA $158 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/b90292fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/e1ce6cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/88cc2eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Smyrna 7.6/10 Good (1000) "Everything was great!! Checked in with ease and staff was great!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tonya CA $96 CA $106 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Dover-Hotels-Quality-Inn.h1781239.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=2025-12-04&endDate=2025-12-05®ionId=7215&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## 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 "The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. " [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Garner Hotel Glen Burnie BWI Airport Area by IHG](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg) ### Garner Hotel Glen Burnie BWI Airport Area by IHG 10/10 Excellent "The staff was very pleasant, check in was smooth and the room was clean and comfortable." [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://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 "Clean room" [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "Staff is amazing & understanding " [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://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 good, clean no evidence of animals , I Am allergic , very decent and affordable. " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Nice room" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "Great friendly staff. Security guard even was friendly and greeted us coming and going. Room was clean and good size. " [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Room was spotless, beds were very comfortable and breakfast was good" [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement." [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Chestertown? > [Comfort Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information): Features full, a seasonal outdoor pool, and free self parking. [Red Roof Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information): Provides 3 bars, a seasonal outdoor pool, and free self parking. [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information): Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. [Historic Inns of Annapolis](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information): Features complimentary wired internet access, an indoor pool, and free self parking. [Pendry Baltimore](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information): Hotel located near Johns Hopkins Hospital. Provides buffet, an indoor pool, and free self parking. ### What is there to see and do in Chestertown? > Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Historical Society of Kent County Maryland, Chestertown Historic District, and Rolphs Wharf Marina during your stay. ### When is the best time to book a hotel with a pool in Chestertown? > You may want to consider a place to stay that offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F. ## 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 Hotels with a Pool in Chestertown on Expedia.com](https://www.expedia.com/Chestertown-Hotels-Hotel-With-Pool.0-0-d7215-tHotelwithPool.Travel-Guide-Filter-Hotels)