Title: Chestertown Vacation Packages 2026 from $784 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestertown Vacations from $784 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Plan, book, and manage your trip all in one place ## Your Chestertown Vacation There's no better way to embark on an adventure than with one of our vacation 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.com/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction), [Rolphs Wharf Marina](https://www.expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) and [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), 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 vacation on Expedia. ## The Latest Chestertown vacation packages Price found within the past 48 hours. Click for updated prices. ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City $784 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 9/10 Wonderful! (3,444 reviews) Room was clean, comfortable, 11th floor was a little bit too high for me. Next trip lower floor. Friendly staff Reviewed on Feb 28, 2026 ![Fenwick Shores, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/9000000/8310000/8308900/8308889/83ce2997_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fenwick Shores, Tapestry Collection by Hilton $922 per person May 11 - May 17 found 3 hours ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 9.4/10 Exceptional! (720 reviews) Clean and courteous staff Reviewed on Feb 17, 2026 ![Sea Breeze Inn](https://images.trvl-media.com/lodging/5000000/4390000/4386400/4386357/9ce5791a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sea Breeze Inn Downtown Ocean City $822 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 6/10 (682 reviews) Very helpful staff and clean property Reviewed on Dec 2, 2025 ![Americana Condos 10th street](https://images.trvl-media.com/lodging/65000000/64560000/64555700/64555604/0a3e0301_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Americana Condos 10th street Downtown Ocean City $1,029 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 8.4/10 Very Good! (19 reviews) straight fire, definitely going back Reviewed on Jun 21, 2025 ![Miramar Condominiums](https://images.trvl-media.com/lodging/91000000/90310000/90308700/90308605/4d3ad6e9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miramar Condominiums Downtown Ocean City $1,368 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Pittsburgh (PIT) to Salisbury (SBY) 9.4/10 Exceptional! (15 reviews) Stayed in unit 505 and it was beautiful! We loved it! Reviewed on Aug 23, 2025 Don't see what you're looking for? See all available trips from Columbus to Chestertown [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-06/2026-04-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](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=PKG_SPRING_PROMO_7215) ### Discover the most popular places to visit in Chestertown ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Washington College 4/5(13 reviews) Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.com/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction) #### Wilmer Park Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.com/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) #### Historical Society of Kent County Maryland You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) ## Chestertown Hotel Deals ![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 refundableReserve now, pay when you stay $101 nightly $112 total Mar 15 - Mar 16 Total with taxes and fees 8.6/10 Excellent! (880 reviews) Room was clean and ready for use. Staff was friendly. Reviewed on Mar 5, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=7215) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/40d24dc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 4 Philadelphia Ct Rosedale MD Fully refundableReserve now, pay when you stay $71 nightly $82 total Mar 16 - Mar 17 Total with taxes and fees 7/10 Good! (1,173 reviews) I had a one night stay at this property, and I came home with bedbugs and bedbug bites all over my body… I actually had to seek medical attention. The condition of the hotel is very poor and disgusting. I believe it serves as a hotel and a homeless shelter in One. Please be aware of this ... Reviewed on Mar 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=3897&PinnedHotelID=3897&HadPinnedHotel=true®ionId=7215) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD Fully refundableReserve now, pay when you stay $157 nightly $179 total Apr 2 - Apr 3 Total with taxes and fees 9/10 Wonderful! (1,880 reviews) Staff were a pleasure. Room was beautiful. Reviewed on Mar 4, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=7215) [See all 1,090 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F7%2F2026&endDate=3%2F8%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. ## Find the Best Chestertown Vacation Packages ## Chestertown Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Population | 5,100 | | Max Temp Winter | 45ºF | | Max Temp Summer | 80ºF | | Top Sights | [Waterman’s Museum](https://www.expedia.com/Watermans-Museum-Rock-Hall.d673471647360921600.Vacation-Attraction), [Historical Society of Kent County Maryland](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) and [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) | ## More vacations you might like ![](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 Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations 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.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Chestertown vacation package cost? ### What are the cheapest months to go to Chestertown? ### How many days is enough for Chestertown? ### Is it worth booking a vacation package to Chestertown? ### How to find the best Chestertown package deals? ### Is it cheaper to book a Chestertown vacation as a package? ### When to book a vacation package to Chestertown? ### Does Expedia offer Book Now, Pay Later Chestertown vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [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) - [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) - [Hotels near Garfield Center for the Arts at the Prince Theater 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