Title: Visit Crumpton: 2026 Travel Guide for Crumpton, Maryland | Expedia.com [Hotels in Crumpton](https://expedia.com/Crumpton-Hotels.d3000440547.Travel-Guide-Hotels)[Vacation Rentals in Crumpton](https://expedia.com/Crumpton-Vacation-Rentals.d3000440547.Travel-Guide-VacationRentals)[Car Rentals in Crumpton](https://expedia.com/Car-Rentals-In-Crumpton.d3000440547.Car-Rental-Guide)[Crumpton Vacation Packages](https://expedia.com/Crumpton.d3000440547.Destination-Travel-Guides) # Crumpton, MD ## Travel Guide ## Visit Crumpton Things to do - Crumpton Hotel Deals - Vacation Rentals in Crumpton ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fairfield Inn & Suites by Marriott Middletown 411 MERRIMAC AVENUE Middletown DE $99 nightly $110 total Mar 29 - Mar 30 Total with taxes and fees Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ... 9.2/10 Wonderful! (359 reviews) Great Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=81261283&PinnedHotelID=81261283&HadPinnedHotel=true®ionId=3000440547) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Chestertown 150 Scheeler Road Chestertown MD $109 nightly $121 total Mar 29 - Mar 30 Total with taxes and fees Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 8.6/10 Excellent! (889 reviews) N/A Reviewed on Mar 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=3000440547) ![Hampton Inn Middletown](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Middletown 117 Sandhill Dr Middletown DE $107 nightly $119 total Mar 30 - Mar 31 Total with taxes and fees Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ... 8.8/10 Excellent! (885 reviews) Good Reviewed on Mar 18, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=1485615&PinnedHotelID=1485615&HadPinnedHotel=true®ionId=3000440547) [See all 182 properties in Crumpton](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F22%2F2026&endDate=3%2F23%2F2026®ionId=3000440547) 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. ![Waterfront w/private pier, pool, Hot Tub, kayaks and in town.](https://images.trvl-media.com/lodging/63000000/62580000/62578000/62577978/41ca91c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront w/private pier, pool, Hot Tub, kayaks and in town. Rock Hall MD Stay at this vacation home in Rock Hall. Enjoy free WiFi, private pools, and a garden. Popular attractions Waterman’s Museum and Rock Hall Harbor are located ... [](https://expedia.com/Rock-Hall-Hotels-Waterfront-Wprivate-Pier.h62577978.Hotel-Information) ![First Floor Studio Apartment in Historic Chestertown](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### First Floor Studio Apartment in Historic Chestertown Chestertown MD Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ... 9.6/10 Exceptional! (108 reviews) Every thing was great Reviewed on Dec 7, 2025 [](https://expedia.com/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Grays Inn Creek Waterfront Pvt. Dock Kayaks & View](https://images.trvl-media.com/lodging/114000000/113910000/113902000/113901993/01c17096_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grays Inn Creek Waterfront Pvt. Dock Kayaks & View Rock Hall MD Stay at this vacation home in Rock Hall. Enjoy a garden, laundry facilities, and patios. Popular attractions The Mainstay and Rock Hall Harbor are located ... 10/10 Exceptional! (2 reviews) We were a group of 15 women participating in a retreat and Grays Creek Inn was the perfect place for us. This was our second rental and we love this place. The large gathering room was great for our programs (esp the big screen tv). The kitchen was adequate for our chef and the bedroom accommodations ... Reviewed on Nov 17, 2025 [](https://expedia.com/Rock-Hall-Hotels-Grays-Inn-Creek-Waterfront-Pvt-Dock-Kayaks-View.h113901993.Hotel-Information) [See all properties in Crumpton](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=3000440547&sort=VACATION_RENTAL) 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. ## Check Crumpton hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-03-21&endDate=2026-03-22)[Mar 21 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-03-21&endDate=2026-03-22) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-03-22&endDate=2026-03-23)[Mar 22 - Mar 23](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-03-22&endDate=2026-03-23) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) ### Popular places to visit #### Crumpton Park After visiting Crumpton Park, make a plan to see the other sights and activities in Crumpton. [](https://expedia.com/Crumpton-Park-Crumpton.d924439696180879360.Vacation-Attraction) ## Cities near Crumpton ![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=512&h=288&q=medium) ### Chestertown ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Crumpton Auction ](https://www.expedia.com/Crumpton-Auction-Hotels.0-l553248621532662415-0.Travel-Guide-Filter-Hotels) - [Hotels near Tilmon's Island Winery ](https://www.expedia.com/Tilmons-Island-Winery-Hotels.0-l553248621532662416-0.Travel-Guide-Filter-Hotels) - [Millington Hotels ](https://www.expedia.com/Millington-Hotels.d3000440734.Travel-Guide-Hotels) - [Vacation Homes in Millington ](https://www.expedia.com/Millington-Private-Vacation-Homes.d3000440734-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [4 Star Hotels in Millington ](https://www.expedia.com/4Star-Millington-Hotels.s40-0-d3000440734.Travel-Guide-Filter-Hotels) - 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[Pet-Friendly Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Pet-Friendly-Hotel.0-0-d7215-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hotels-With-Indoor-Pool.0-0-d7215-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Historic Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Historic-Hotel.0-0-d7215-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Extended Stay Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Extended-Stay-Hotels.0-0-d7215-tExtendedStayHotels.Travel-Guide-Filter-Hotels) - [Motels in Chestertown ](https://www.expedia.com/Chestertown-Motels.d7215-aaMotels.Travel-Guide-Accommodation) - [Marriott Hotels & Resorts in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Marriott-Hotels-Resorts.0-0-d7215--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Chestertown ](https://www.expedia.com/5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Luxury-Hotel.0-0-d7215-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hilton-Hotels.0-0-d7215--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Resorts in Chestertown ](https://www.expedia.com/Chestertown-Resorts.d7215-aaResorts.Travel-Guide-Accommodation) - [Hotels with Bars in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Bar-Hotel.0-0-d7215-tBarHotel.Travel-Guide-Filter-Hotels) - [La Quinta Inn & Suites Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-La-Quinta-Inn-Suites.0-0-d7215--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hotel-With-Pool.0-0-d7215-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Wyndham Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Wyndham-Hotels.0-0-d7215--bWyndhamHotels.Travel-Guide-Filter-Hotels) - [Hotels with Air Conditioning in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hotels-With-Air-Conditioning.0-0-d7215-tHotelswithAirConditioning.Travel-Guide-Filter-Hotels) - [Golf Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Golf-Hotel.0-0-d7215-tGolfHotel.Travel-Guide-Filter-Hotels) - [Vacation Homes in Chestertown ](https://www.expedia.com/Chestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels with an Outdoor Pool in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hotels-With-Outdoor-Pool.0-0-d7215-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels) - [Cottages in Chestertown ](https://www.expedia.com/Chestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Couples-Resorts-Hotels.0-0-d7215-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Family-Hotel.0-0-d7215-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Condo Rentals in Chestertown ](https://www.expedia.com/Chestertown-Condos.d7215-aaCondos.Travel-Guide-Accommodation) - [Best Western Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Best-Western.0-0-d7215--bBestWestern.Travel-Guide-Filter-Hotels) - [Hotels near Washington College ](https://www.expedia.com/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels near River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) - [Flights to Millington ](https://www.expedia.com/Cheap-Flights-To-Millington.d3000440734.Travel-Guide-Flights) - [Flights from Millington ](https://www.expedia.com/lp/flights/3000440734/flights-from-millington) - [Flights to Sudlersville ](https://www.expedia.com/Cheap-Flights-To-Sudlersville.d6359188.Travel-Guide-Flights) - [Flights from Sudlersville ](https://www.expedia.com/lp/flights/6359188/flights-from-sudlersville) - [Flights from Kennedyville ](https://www.expedia.com/lp/flights/3000440679/flights-from-kennedyville) - [Flights from Massey ](https://www.expedia.com/lp/flights/3000440702/flights-from-massey) - [Flights to Galena ](https://www.expedia.com/Cheap-Flights-To-Galena.d106992.Travel-Guide-Flights) - [Flights from Barclay ](https://www.expedia.com/lp/flights/553248634998993874/flights-from-barclay) - [Flights to Church Hill ](https://www.expedia.com/Cheap-Flights-To-Church-Hill.d6359186.Travel-Guide-Flights) - [Flights to Chestertown ](https://www.expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights) - [Chicago to Chestertown ](https://www.expedia.com/lp/flights/178248/7215/chicago-to-chestertown) - [Tilmon's Island Winery ](https://www.expedia.com/Tilmons-Island-Winery-Sudlersville.d553248621532662416.Vacation-Attraction) - [Visit Sudlersville ](https://www.expedia.com/Sudlersville.dx6359188) - [Visit Kennedyville ](https://www.expedia.com/Kennedyville.dx3000440679) - [Visit Church Hill ](https://www.expedia.com/Church-Hill.dx6359186) - [Visit Chestertown ](https://www.expedia.com/Chestertown.dx7215) - [Rolphs Wharf Marina ](https://www.expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) - [Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction) - [Chestertown Vacations ](https://www.expedia.com/Chestertown.d7215.Destination-Travel-Guides) - [Washington College ](https://www.expedia.com/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction) - [River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Chestertown.d553248621532662298.Vacation-Attraction) - [Wilmer Park ](https://www.expedia.com/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [Car rentals near Crumpton Auction ](https://www.expedia.com/Car-Rentals-In-Crumpton-Auction.d553248621532662415.Car-Rental-Guide) - [Car rentals near Sudlersville ](https://www.expedia.com/Car-Rentals-In-Sudlersville.d6359188.Car-Rental-Guide) - [Car rentals near Massey ](https://www.expedia.com/Car-Rentals-In-Massey.d3000440702.Car-Rental-Guide) - [Car rentals near Galena ](https://www.expedia.com/Car-Rentals-In-Galena.d106992.Car-Rental-Guide) - [Car rentals near Church Hill ](https://www.expedia.com/Car-Rentals-In-Church-Hill.d6359186.Car-Rental-Guide) - [Car rentals near Chestertown ](https://www.expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide) - [Budget Rental Cars in Chestertown ](https://www.expedia.com/Budget-Car-Rentals-In-Chestertown.d7215-c39.Car-Rental-Guide-Suppliers) - [Van Car Rentals in Chestertown ](https://www.expedia.com/Van-Car-Rentals-In-Chestertown.d7215-tVan.Car-Rental-Guide-Class) - [U-Save Rental Cars in Chestertown ](https://www.expedia.com/U-Save-Car-Rentals-In-Chestertown.d7215-c34.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Chestertown ](https://www.expedia.com/Thrifty-Car-Rental-Car-Rentals-In-Chestertown.d7215-c45.Car-Rental-Guide-Suppliers) - [Millington Vacation Rentals ](https://www.expedia.com/Millington-Vacation-Rentals.d3000440734.Travel-Guide-VacationRentals) - [Massey Vacation Rentals ](https://www.expedia.com/Massey-Vacation-Rentals.d3000440702.Travel-Guide-VacationRentals) - [Chestertown Vacation Rentals ](https://www.expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals) - Cities near Crumpton - Places of interest [Chestertown](https://expedia.com/Chestertown.dx7215) - [Chesapeake Bay ](https://expedia.com/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Washington College ](https://expedia.com/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction) - [Bohemia Vista Marina ](https://expedia.com/Bohemia-Vista-Marina-Chesapeake-City.d553248621558141305.Vacation-Attraction) - [Betterton Beach ](https://expedia.com/Betterton-Beach-Maryland.d553248635983992889.Vacation-Attraction) - [Rock Hall Harbor ](https://expedia.com/Rock-Hall-Harbor-Rock-Hall.d553248621561173703.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.com/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) - [Elk Neck State Park ](https://expedia.com/Elk-Neck-State-Park-North-East.d553248621532662916.Vacation-Attraction) - [Historical Society of Kent County Maryland ](https://expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Rolphs Wharf Marina ](https://expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) - [Mount Harmon Plantation ](https://expedia.com/Mount-Harmon-Plantation-Earleville.d553248621561879694.Vacation-Attraction) - [Frog Hollow Golf Club ](https://expedia.com/Frog-Hollow-Golf-Club-Middletown.d6187475.Vacation-Attraction) - [River Arts Chestertown ](https://expedia.com/River-Arts-Chestertown-Chestertown.d553248621532662298.Vacation-Attraction) - [Ferry Park ](https://expedia.com/Ferry-Park-Rock-Hall.d553248621561234961.Vacation-Attraction) - [Wilmer Park ](https://expedia.com/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [The Mainstay ](https://expedia.com/The-Mainstay-Rock-Hall.d553248621532662296.Vacation-Attraction) - [Garfield Center for the Arts at the Prince Theater ](https://expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction)