Title: Chestertown Vacation Packages 2026 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx89045)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide) ![](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestertown Vacations ## 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 plenty to like about Chestertown, from its rich history to its spectacular views. When you're ready to spend a bit of time in this interesting city, our Chestertown vacation packages will be ideal for you. [Friends Lake](https://www.expedia.com/Friends-Lake-Lake-George.d553248635976195601.Vacation-Attraction), [Loon Lake](https://www.expedia.com/Loon-Lake-Lake-George.d553248635976196050.Vacation-Attraction) and [Loon Lake Beach](https://www.expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) are just a few of the sights you'll want to see during your trip to Chestertown. Don't put off your visit to this destination any longer. Your dream Chestertown vacation is only a few clicks away with Expedia. ### Discover the most popular places to visit in Chestertown #### Loon Lake Beach If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) ## Chestertown Hotel Deals ![The Fern Lodge](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Fern Lodge 46 Fiddlehead Bay Rd. Chestertown NY $478 nightly $531 total Feb 10 - Feb 11 Total with taxes and fees 9.8/10 Exceptional! (47 reviews) I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! Reviewed on Dec 27, 2025 [](https://expedia.com/Hotel-Search?startDate=2%2F10%2F2026&endDate=2%2F11%2F2026&selected=1538972&PinnedHotelID=1538972&HadPinnedHotel=true®ionId=89045) ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown NY $680 nightly $755 total Mar 8 - Mar 9 Total with taxes and fees 9.8/10 Exceptional! (111 reviews) Great house. Great location Reviewed on Jan 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Six Flags Great Escape Lodge & Indoor Waterpark 89 Six Flags Dr Queensbury NY $169 nightly $188 total Feb 12 - Feb 13 Total with taxes and fees 7.8/10 Good! (1,514 reviews) Clean room, food at the restaurant was great Reviewed on Feb 4, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=1385446&PinnedHotelID=1385446&HadPinnedHotel=true®ionId=89045) [See all 1,533 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F10%2F2026&endDate=2%2F11%2F2026®ionId=89045) 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 Beach Vacation Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown vacation. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organize your trip to Chestertown the quick and easy way by locking in one of our Chestertown vacation deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 2 miles (3 km) from the downtown area. ## Chestertown Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 680 | | Max Temp Winter | 30ºF | | Max Temp Summer | 75ºF | | Top Sights | [Gore Mountain Ski Resort](https://www.expedia.com/Gore-Mountain-Ski-Resort-North-Creek.d6326108.Vacation-Attraction), [Loon Lake Beach](https://www.expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) and [Natural Stone Bridge and Caves](https://www.expedia.com/Natural-Stone-Bridge-And-Caves-Pottersville.d6230830.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) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](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? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on 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