Title: Chestertown Holidays 2026 | Expedia.co.uk [Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Holiday Rentals in Chestertown](https://expedia.co.uk/Chestertown-Holiday-Rentals.d7215.Travel-Guide-HolidayRentals)[Chestertown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chestertown.d7215.Car-Hire-Guide) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestertown Holidays ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected #### Your Chestertown Holiday There's no better way to embark on an adventure than with one of our holiday packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to [Washington College](https://www.expedia.co.uk/Washington-College-Chestertown.d553248621561000403.Attraction), [Rolphs Wharf Marina](https://www.expedia.co.uk/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Attraction) and [Garfield Centre for the Arts at the Prince Theatre](https://www.expedia.co.uk/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Attraction), some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown holiday on Expedia. ## Chestertown Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 5,100 | | Max Temp Winter | 7ºC | | Max Temp Summer | 27ºC | | Top Sights | [Historical Society of Kent County Maryland](https://www.expedia.co.uk/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Attraction), [Garfield Centre for the Arts at the Prince Theatre](https://www.expedia.co.uk/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Attraction) and [Crow Farm and Vineyard](https://www.expedia.co.uk/Crow-Farm-And-Vineyard-Maryland.d553248621532662417.Attraction) | ## Top hotels in Chestertown ![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 Fully refundable £103 19 Apr - 20 Apr includes taxes & fees 8.6/10 Excellent! (893 reviews) Clean, quiet. Reviewed on 29 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=7215) ![Blue Heron Farm Waterfront Chalet](https://images.trvl-media.com/lodging/114000000/113500000/113490800/113490795/9013103f_edited_936d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Blue Heron Farm Waterfront Chalet Chestertown MD 10/10 Exceptional! (2 reviews) Location! Location! Reviewed on 22 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=113490795&PinnedHotelID=113490795&HadPinnedHotel=true®ionId=7215) [](https://expedia.co.uk/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=113490795&PinnedHotelID=113490795&HadPinnedHotel=true®ionId=7215) ![Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!](https://images.trvl-media.com/lodging/114000000/113420000/113417900/113417810/w904h683x60y0-5649826f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! Chestertown MD 10/10 Exceptional! (16 reviews) We brought our Lab with us. She loved looking out all the windows. She was afraid to walk up the open stairs but was content to sleep on the first floor. We enjoyed our stay at Outrange. Very quiet and secluded. Short walk to River. Reviewed on 22 Mar 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=113417810&PinnedHotelID=113417810&HadPinnedHotel=true®ionId=7215) [](https://expedia.co.uk/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=113417810&PinnedHotelID=113417810&HadPinnedHotel=true®ionId=7215) [See all 1,101 properties in Chestertown](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026®ionId=7215) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app