Title: The Best 2 Star Hotels in Crumpton, MD from $75 | Expedia.com [Crumpton Travel Guide](https://expedia.com/Crumpton.dx3000440547)[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)[Flights to Crumpton](https://expedia.com/Cheap-Flights-To-Crumpton.d3000440547.Travel-Guide-Flights)[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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Crumpton 2 Star Hotels Tonight [Mar 13 - Mar 14](https://www.expedia.com/Hotel-Search?regionId=3000440547&startDate=2026-03-13&endDate=2026-03-14&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000440547&startDate=2026-03-14&endDate=2026-03-15&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000440547&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=3000440547&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Crumpton 2-star hotels ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/9a7a154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown [](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (885 reviews) "Staying is peaceful and the rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert $105 nightly $116 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/7e87d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown [](https://www.expedia.com/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) Middletown 8.8/10 Excellent (883 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken $98 nightly $108 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/6af27243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/b95d3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3cc8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown by IHG [](https://www.expedia.com/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) Middletown 9.2/10 Wonderful (671 reviews) "Great rooms and awesome hospitality " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tonya $111 nightly $123 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![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) ![Standard Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/735621f3.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/2000000/1790000/1781300/1781239/02f5a1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Quality Inn Smyrna [](https://www.expedia.com/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information) Smyrna 7.6/10 Good (1,000 reviews) "My visit at the Hotel was amazing & peaceful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Milton $77 nightly $85 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown [](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) Chestertown 7.2/10 Good (429 reviews) "Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linette $71 nightly $79 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![Deluxe Room | Interior detail](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/0de71463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double or Twin Room | Premium bedding, down comforters, individually furnished, desk](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/db980bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathtub, towels](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/w1290h1713x0y0-d518f5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/85b5182c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax Inn Smyrna [](https://www.expedia.com/Smyrna-Hotels-Relax-Inn-Smyrna.h89677382.Hotel-Information) Smyrna 7.8/10 Good (93 reviews) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick $79 nightly $85 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Smyrna-Hotels-Relax-Inn-Smyrna.h89677382.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/w2069h1549x0y3-dd3dc42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (Haven) | Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/89c7676f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, soundproofing, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/5b38a1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027300/119027214/bb00a986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Haven Point Inn and Gallery [](https://www.expedia.com/Rock-Hall-Hotels-Haven-Point-Inn-And-Gallery.h119027214.Hotel-Information) Rock Hall [](https://www.expedia.com/Rock-Hall-Hotels-Haven-Point-Inn-And-Gallery.h119027214.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/4ed42fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Desk, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/24031bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/1af5cb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/w353h265x3y3-b7952ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Inn [](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information) Chestertown 5.2/10 (175 reviews) "Rooms are clean, staf was helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl $68 nightly $75 total Mar 14 - Mar 15 Total with taxes and fees [](https://www.expedia.com/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19450000/19446700/19446692/b6c7ae16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed | View from room](https://images.trvl-media.com/lodging/20000000/19450000/19446700/19446692/d7a976f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19450000/19446700/19446692/a2be27f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/20000000/19450000/19446700/19446692/828a2806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillside Motel [](https://www.expedia.com/Centreville-Hotels-Hillside-Motel.h19446692.Hotel-Information) Centreville 5.0/10 (45 reviews) "I never had a chance to stay because the office closed at 9 pm and NO ONE would answer the phone. In fact, someone picked up the phone and hung up on me. What hotel doesnt have a person on site at all times?!! I spoke with a gentleman at the liquor store and he said he heard of this problem every weekend. If you're going to close at 9 make it in BOLD PRINT." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim [](https://www.expedia.com/Centreville-Hotels-Hillside-Motel.h19446692.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Crumpton-Hotels.s20-0-d3000440547.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Crumpton-Hotels.s20-0-d3000440547.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Crumpton. ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott Middletown 411 MERRIMAC AVENUE Middletown DE $99 nightly $110 total Mar 22 - Mar 23 Total with taxes and fees 9.2/10 Wonderful! (354 reviews) [](https://expedia.com/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![The Lodge at Great Oak Landing](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Lodge at Great Oak Landing 22170 Great Oak Landing Rd Chestertown MD $124 nightly $137 total Mar 16 - Mar 17 Total with taxes and fees 7.8/10 Good! (77 reviews) [](https://expedia.com/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Inn at Huntingfield Creek](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn at Huntingfield Creek 4928 Eastern Neck Rd Rock Hall MD $156 nightly $173 total Mar 15 - Mar 16 Total with taxes and fees 10/10 Exceptional! (61 reviews) [](https://expedia.com/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) Still don't see what you're looking for? [See all properties in Crumpton.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=3000440547&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=3000440547&star=20&star=20&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=3000440547&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=3000440547&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=3000440547&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=3000440547&star=20&star=20&amenities=WATER_PARK) 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. ## Top Crumpton Hotel Reviews ![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa_y.jpg) ### Red Roof Inn & Suites Chestertown 4/10 Poor "Unfriendly staff. Dirty" [](https://expedia.com/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ## Find out more about Crumpton ## Crumpton Motel Guide Planning a getaway with only a few bucks to spare? Expedia can help! With the inexpensive rates at the top motels in Crumpton, Maryland you can put together the vacation of your dreams without spending every penny of your yearly travel budget. These smaller places are ideal if you need a home base that lets you easily explore the local sights; many of the best motels in Crumpton are located near major freeways and public transportation. Plus, when you book a cheap deal on a motel in Crumpton, you’ll find quiet rooms, complimentary toiletries, and comfortable sleeping areas, so you can unwind after a long day. No matter which motel you choose, don't forget to use the travel tools at Expedia to search for local discounts, compare rates on the hottest motels, and plan your next vacation. You won't believe how budget-friendly an amazing getaway can be. Also, feel free to check out the [motels near me](https://www.expedia.com/g/u/hotels-near-me) page to find the cheapest deals on motels near your current location. ## Frequently asked questions ### How much does it cost to stay in a 2-star hotel in Crumpton? ### What is the difference between a 2-star Crumpton hotel and a 3-star hotel? ## 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) - [4 Star Hotels in Millington ](https://www.expedia.com/4Star-Millington-Hotels.s40-0-d3000440734.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) - [5 Star Hotels in Sudlersville ](https://www.expedia.com/5Star-Sudlersville-Hotels.s50-0-d6359188.Travel-Guide-Filter-Hotels) - [Sudlersville Hotels ](https://www.expedia.com/Sudlersville-Hotels.d6359188.Travel-Guide-Hotels) - [Hotels near Crow Farm and Vineyard ](https://www.expedia.com/Crow-Farm-And-Vineyard-Hotels.0-l553248621532662417-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Kennedyville ](https://www.expedia.com/4Star-Kennedyville-Hotels.s40-0-d3000440679.Travel-Guide-Filter-Hotels) - [Kennedyville Hotels ](https://www.expedia.com/Kennedyville-Hotels.d3000440679.Travel-Guide-Hotels) - [Apartments in Kennedyville ](https://www.expedia.com/Kennedyville-Apartments.d3000440679-aaApartments.Travel-Guide-Accommodation) - [4 Star Hotels in Massey ](https://www.expedia.com/4Star-Massey-Hotels.s40-0-d3000440702.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Galena ](https://www.expedia.com/4Star-Galena-Hotels.s40-0-d106992.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Galena ](https://www.expedia.com/5Star-Galena-Hotels.s50-0-d106992.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Galena ](https://www.expedia.com/3Star-Galena-Hotels.s30-0-d106992.Travel-Guide-Filter-Hotels) - [Massey Hotels ](https://www.expedia.com/Massey-Hotels.d3000440702.Travel-Guide-Hotels) - [Vacation Homes in Massey ](https://www.expedia.com/Massey-Private-Vacation-Homes.d3000440702-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Motels in Massey ](https://www.expedia.com/Massey-Motels.d3000440702-aaMotels.Travel-Guide-Accommodation) - [Galena Hotels ](https://www.expedia.com/Galena-Hotels.d106992.Travel-Guide-Hotels) - [B&B in Galena ](https://www.expedia.com/Galena-Bed-And-Breakfast.d106992-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Galena ](https://www.expedia.com/Galena-Guest-Houses.d106992-aaGuestHouses.Travel-Guide-Accommodation) - [Barclay Hotels ](https://www.expedia.com/Barclay-Hotels.d553248634998993874.Travel-Guide-Hotels) - [5 Star Hotels in Chestertown ](https://www.expedia.com/5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels) - [Church Hill Hotels ](https://www.expedia.com/Church-Hill-Hotels.d6359186.Travel-Guide-Hotels) - [Hotels near Rolphs Wharf Marina ](https://www.expedia.com/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels) - [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) - [Hotels with Suites in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hotel-Suites.0-0-d7215-tHotelSuites.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Romantic-Hotel.0-0-d7215-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Spa-Hotel.0-0-d7215-tSpaHotel.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Chestertown ](https://www.expedia.com/Chestertown-Cabins.d7215-aaCabins.Travel-Guide-Accommodation) - [Apartments in Chestertown ](https://www.expedia.com/Chestertown-Apartments.d7215-aaApartments.Travel-Guide-Accommodation) - [Red Roof Inn Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Red-Roof-Inn.0-0-d7215--bRedRoofInn.Travel-Guide-Filter-Hotels) - [Beach Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Beach-Hotel.0-0-d7215-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Hotels-With-Restaurants.0-0-d7215-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [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) - [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) - [Golf Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Golf-Hotel.0-0-d7215-tGolfHotel.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) - [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) - [Hotels & Resorts for Couples in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Couples-Resorts-Hotels.0-0-d7215-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Cottages in Chestertown ](https://www.expedia.com/Chestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation) - [Family Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Family-Hotel.0-0-d7215-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Chestertown ](https://www.expedia.com/Chestertown-Hotels-Best-Western.0-0-d7215--bBestWestern.Travel-Guide-Filter-Hotels) - [Condo Rentals in Chestertown ](https://www.expedia.com/Chestertown-Condos.d7215-aaCondos.Travel-Guide-Accommodation) - [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) - [Rolphs Wharf Marina ](https://www.expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) - [Visit Church Hill ](https://www.expedia.com/Church-Hill.dx6359186) - [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) - [Visit Chestertown ](https://www.expedia.com/Chestertown.dx7215) - [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)