Title: Chestertown Holidays 2026 | Expedia.co.uk [Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Holiday Rentals in Chestertown](https://expedia.co.uk/Chestertown-Holiday-Rentals.d89045.Travel-Guide-HolidayRentals)[Chestertown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chestertown.d89045.Car-Hire-Guide) ![](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.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 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 holiday packages will be ideal for you. [Friends Lake](https://www.expedia.co.uk/Friends-Lake-Lake-George.d553248635976195601.Attraction), [Loon Lake](https://www.expedia.co.uk/Loon-Lake-Lake-George.d553248635976196050.Attraction) and [Loon Lake Beach](https://www.expedia.co.uk/Loon-Lake-Beach-Chestertown.d553248621554184980.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 holiday is only a few clicks away with Expedia. ### Chestertown Beach Holiday Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown holiday. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organise your trip to Chestertown the quick and easy way by locking in one of our Chestertown holiday deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 2 miles from the downtown area. ## Chestertown Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 680 | | Max Temp Winter | \-1.11ºC | | Max Temp Summer | 24ºC | | Top Sights | [Gore Mountain Ski Resort](https://www.expedia.co.uk/Gore-Mountain-Ski-Resort-North-Creek.d6326108.Attraction), [Loon Lake Beach](https://www.expedia.co.uk/Loon-Lake-Beach-Chestertown.d553248621554184980.Attraction) and [Natural Stone Bridge and Caves](https://www.expedia.co.uk/Natural-Stone-Bridge-And-Caves-Pottersville.d6230830.Attraction) | ## Top hotels in Chestertown ![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 £329 29 Mar - 30 Mar includes taxes & fees 10/10 Exceptional! (52 reviews) I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! Reviewed on 27 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%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 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) [](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) ![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure. Chestertown NY 10/10 Exceptional! (3 reviews) This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for ... Reviewed on 25 Mar 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true®ionId=89045) [](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true®ionId=89045) [See all 1,532 properties in Chestertown](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%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. ![](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