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 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_3000440547) - Crumpton Hotel Deals - Vacation Rentals in Crumpton ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fairfield Inn & Suites by Marriott Middletown 411 MERRIMAC AVENUE Middletown DE $97 nightly $108 total Mar 8 - Mar 9 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! (350 reviews) Clean room, felt very safe and secure, free parking, staff very friendly, plenty of eating and shopping close by Reviewed on Feb 22, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=81261283&PinnedHotelID=81261283&HadPinnedHotel=true®ionId=3000440547) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Chestertown 150 Scheeler Road Chestertown MD $101 nightly $112 total Mar 8 - Mar 9 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! (879 reviews) I reserved a suite for two nights on 12/26/25\. Almost 2 months in advance. When I arrived the check-in girl said that she downgraded my room to a double because they were overbooked and since I only two people in my group she gave my suite to a party with 4 people because they needed more room than ... Reviewed on Feb 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=3000440547) ![Hampton Inn Middletown](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Middletown 117 Sandhill Dr Middletown DE $95 nightly $106 total Mar 4 - Mar 5 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! (880 reviews) Clean and modern Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=1485615&PinnedHotelID=1485615&HadPinnedHotel=true®ionId=3000440547) [See all 175 properties in Crumpton](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F26%2F2026&endDate=2%2F27%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. ![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) ![Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!](https://images.trvl-media.com/lodging/114000000/113420000/113417900/113417810/1d961d4b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! Chestertown MD Stay at this cabin in Chestertown. Enjoy a garden, laundry facilities, and patios. Popular attractions Chase Island and Crumpton Auction are located nearby. 10/10 Exceptional! (14 reviews) Great house, great property, great hosts Reviewed on Feb 5, 2026 [](https://expedia.com/Chestertown-Hotels-Outrange-At-Blue-Heron-Farm-Pet-Friendly-Cabin-At-Waterfront-Farm.h113417810.Hotel-Information) ![Waterfront w/private pier, pool, Hot Tub, kayaks and in town.](https://images.trvl-media.com/lodging/63000000/62580000/62578000/62577978/7dd2d038_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) [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=2026-02-25&endDate=2026-02-26)[Feb 25 - Feb 26](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-02-25&endDate=2026-02-26) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-02-26&endDate=2026-02-27)[Feb 26 - Feb 27](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2026-02-26&endDate=2026-02-27) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2%2F27%2F2026&endDate=3%2F1%2F2026)[Feb 27 - Mar 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=2%2F27%2F2026&endDate=3%2F1%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026)[Mar 6 - Mar 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000440547&startDate=3%2F6%2F2026&endDate=3%2F8%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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[Motels in Church Hill ](https://www.expedia.com/Church-Hill-Motels.d6359186-aaMotels.Travel-Guide-Accommodation) - [Chestertown Hotels ](https://www.expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels) - [Hotels near Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) - [B&B in Chestertown ](https://www.expedia.com/Chestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Cheap-Hotels.0-0-d7215-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Oceanfront-Hotels.0-0-d7215-tOceanfrontHotels.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) - [Rock Hall Harbor ](https://expedia.com/Rock-Hall-Harbor-Rock-Hall.d553248621561173703.Vacation-Attraction) - [Betterton Beach ](https://expedia.com/Betterton-Beach-Maryland.d553248635983992889.Vacation-Attraction) - [Bohemia Vista Marina ](https://expedia.com/Bohemia-Vista-Marina-Chesapeake-City.d553248621558141305.Vacation-Attraction) - 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