Title: Chestertown Vacation Packages 2026 from $727 | 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 $727 ## 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. ![Ashore Resort & Beach Club](https://images.trvl-media.com/lodging/1000000/30000/20400/20346/e36f7efc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ashore Resort & Beach Club North Ocean City $727 per person Apr 2 - Apr 7 found 20 hours ago Roundtrip non-stop flight included Minneapolis (MSP) to Salisbury (SBY) 8.2/10 Very Good! (1,825 reviews) Clean, comfortable and quiet. Reviewed on Dec 28, 2025 ![Boardwalk One](https://images.trvl-media.com/lodging/3000000/2060000/2053600/2053558/73b85086_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boardwalk One Downtown Ocean City $792 per person Apr 2 - Apr 7 found 20 hours ago Roundtrip non-stop flight included Minneapolis (MSP) to Salisbury (SBY) 7.4/10 Good! (170 reviews) Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo. Reviewed on Oct 1, 2025 ![Cypress River Inn & Spa](https://images.trvl-media.com/lodging/120000000/119300000/119292000/119291924/57fdc3d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cypress River Inn & Spa $1,100 per person Apr 2 - Apr 7 found 14 hours ago Roundtrip non-stop flight included Minneapolis (MSP) to Salisbury (SBY) No reviews ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City $909 per person Apr 12 - Apr 18 found 1 day ago Roundtrip non-stop flight included Baltimore (BWI) to Salisbury (SBY) 9/10 Wonderful! (3,316 reviews) The only place we stay when we go to Ocean City. Great location, plenty of parking, friendly staff, good food, 2 arcade areas! On the boardwalk, far enough from the inlet crowds, but a nice walk. Great beach location & views. Reviewed on Feb 1, 2026 ![Club Ocean Villas II](https://images.trvl-media.com/lodging/63000000/62980000/62974900/62974891/a8f648b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Club Ocean Villas II North Ocean City $1,169 per person Apr 12 - Apr 18 found 1 day ago Roundtrip non-stop flight included Baltimore (BWI) to Salisbury (SBY) 8.6/10 Excellent! (58 reviews) Did not like the outdated furniture, small televisions and the hot tub wasn’t sanitized until the next day. Notified office told them hot tub cover was not on and they said they were waiting for a new cover to come in. Pools don’t open until 10 There were ants on the counter tops and the first night we were locked out . Staff said they had us listed as checked out . We did get new cards immediately. We have stayed in the condos for over 30 years Disappointed especially for paying g what we paid Reviewed on Jul 7, 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/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BWI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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 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) #### Rolphs Wharf Marina Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area. [](https://expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.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/a1387f46_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Chestertown 150 Scheeler Road Chestertown MD Fully refundableReserve now, pay when you stay $97 nightly $108 total Feb 28 - Mar 1 Total with taxes and fees 8.4/10 Very Good! (870 reviews) Polite and kind hotel manager Reviewed on Jan 25, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F28%2F2026&endDate=3%2F1%2F2026&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=7215) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD Fully refundableReserve now, pay when you stay $229 nightly $261 total Feb 26 - Feb 27 Total with taxes and fees 9/10 Wonderful! (1,884 reviews) Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back! Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=7215) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_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 $64 nightly $74 total Feb 8 - Feb 9 Total with taxes and fees 7/10 Good! (1,152 reviews) Clean room, easy check in Reviewed on Jan 24, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=3897&PinnedHotelID=3897&HadPinnedHotel=true®ionId=7215) [See all 1,084 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%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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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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