Title: Chestertown Vacation Packages 2026 from $548 | 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 from $548 ## 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. ## The Latest Chestertown vacation packages Price found within the past 48 hours. Click for updated prices. ![Days Inn by Wyndham Queensbury/Lake George](https://images.trvl-media.com/lodging/1000000/10000/4500/4493/ce4c5c26_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Days Inn by Wyndham Queensbury/Lake George $548 per person May 1 - May 5 found 24 hours ago Roundtrip flight included Midland (MAF) to Glens Falls (GFL) 5.6/10 (1,000 reviews) A place to stay for a night, not very clean,bed sheet only on mattress no pad, no blanket. room was warm and shower was ok. Reviewed on Dec 18, 2025 ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Queensbury Hotel $806 per person May 1 - May 5 found 24 hours ago Roundtrip flight included Midland (MAF) to Glens Falls (GFL) 9.4/10 Exceptional! (1,423 reviews) Staff was lovely. Rooms are lacking power outlets and bathrooms has no counter space Reviewed on Feb 2, 2026 ![The Alpine Lodge](https://images.trvl-media.com/lodging/6000000/5180000/5179400/5179323/c5361517_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Alpine Lodge $743 per person May 1 - May 5 found 24 hours ago Roundtrip flight included Midland (MAF) to Glens Falls (GFL) 9/10 Wonderful! (650 reviews) The room was clean and the bed was comfy. Our check-in instructions arrived after check-in time. For some reason the fire alarm went off 3 times, and woke us up on our one day to sleep in. There are limited dining options in the area. It was a great location close to Gore - love the mountain! Reviewed on Jan 14, 2026 ![North Creek Lodge at Gore Mountain](https://images.trvl-media.com/lodging/8000000/7520000/7510500/7510444/29d03cb5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### North Creek Lodge at Gore Mountain $729 per person May 1 - May 5 found 24 hours ago Roundtrip flight included Midland (MAF) to Glens Falls (GFL) 8/10 Very Good! (402 reviews) Great place close to Gore! Reviewed on Jan 20, 2026 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=GFL&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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 $527 nightly $586 total Mar 8 - Mar 9 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=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=1538972&PinnedHotelID=1538972&HadPinnedHotel=true®ionId=89045) ![Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/c6d64672_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George Chestertown NY 9.8/10 Exceptional! (73 reviews) Excellent stocked kitchen, warm fireplace. Spotlessly cleaned. We loved it! Had everything we could have possibly needed. Warm, comfortable, and beautiful scenery. Reviewed on Jan 3, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=76320395&PinnedHotelID=76320395&HadPinnedHotel=true®ionId=89045) [](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=76320395&PinnedHotelID=76320395&HadPinnedHotel=true®ionId=89045) ![Elizabeth. A Guest House Near Lake George. ](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/8b4efd64_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elizabeth. A Guest House Near Lake George. Chestertown NY 8/10 Very Good! (35 reviews) The house was beautiful and charming and plenty of space. We have no complaints but recommend hand towels in the bathrooms. Probably will look up this place again for a skiing trip this winter. Reviewed on Aug 10, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=33955795&PinnedHotelID=33955795&HadPinnedHotel=true®ionId=89045) [](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=33955795&PinnedHotelID=33955795&HadPinnedHotel=true®ionId=89045) [See all 1,535 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%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) 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![](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