Title: Chestertown Vacation Packages & Trips 2025/2026 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide) ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestertown Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Julie Miller - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 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.ca/Friends-Lake-Lake-George.d553248635976195601.Vacation-Attraction), [Loon Lake](https://www.expedia.ca/Loon-Lake-Lake-George.d553248635976196050.Vacation-Attraction) and [Loon Lake Beach](https://www.expedia.ca/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. ### 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 3 kilometres from the downtown area. ## Ready to book your vacation to Chestertown? Choose your dates ## Chestertown Hotel Deals ![Pine Tree Motel & Cabins](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/29c27732_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pine Tree Motel & Cabins 5537 State Route 8, Chestertown, NY CA $241 CA $268 total Sep 22 - Sep 23 includes taxes & fees 9.2/10 Wonderful! (139 reviews) "Came here for the weekend with my husband and my dog! The place is really nice, clean" Reviewed on Sep 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=8355292&PinnedHotelID=8355292&HadPinnedHotel=true®ionId=89045) ![Friends Lake Inn](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Friends Lake Inn 963 Friends Lake Rd, Chestertown, NY CA $309 CA $343 total Sep 17 - Sep 18 includes taxes & fees 8.6/10 Excellent! (100 reviews) "Staff was great. The inn is unique. Perfect!" Reviewed on Sep 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F09%2F2025&endDate=18%2F09%2F2025&selected=9675030&PinnedHotelID=9675030&HadPinnedHotel=true®ionId=89045) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Queensbury Hotel 88 Ridge St, Glens Falls, NY Fully refundableReserve now, pay when you stay CA $161 CA $178 total Oct 14 - Oct 15 includes taxes & fees 9.2/10 Wonderful! (1,354 reviews) "The property was very nice. It was quiet and very clean. The restaurant was very good and the service was amazing. The pool was a little to cold for swimming as it was a cooler day and there was a lot of chlorine in it." Reviewed on Sep 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F10%2F2025&endDate=15%2F10%2F2025&selected=40334&PinnedHotelID=40334&HadPinnedHotel=true®ionId=89045) [See all 1,551 properties in Chestertown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®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 Vacations [](https://expedia.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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.ca/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.ca/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.ca/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.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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.ca/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) ## Other vacations you might like - Nearby Cities - Best vacation destinations by month - [New York Vacations](https://expedia.ca/New-York.d178293.Destination-Travel-Guides) - [Buffalo Vacations](https://expedia.ca/Buffalo.d602674.Destination-Travel-Guides) - [Newark Vacations](https://expedia.ca/Newark.d601760.Destination-Travel-Guides) - [Jersey City Vacations](https://expedia.ca/Jersey-City.d6023404.Destination-Travel-Guides) - [Rochester Vacations](https://expedia.ca/Rochester.d602966.Destination-Travel-Guides) - [January Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-january) - [February Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-february) - [March Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-march) - [April Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-april) - [May Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-may) - [June Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-june) - [July Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-july) - [August Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-august) - [September Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-september) - [October Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-october) - [November Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-november) - [December Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-december) \* 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 on select hotels and earn double points 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 ![QR code to download the app](https://a.travel-assets.com/mad-service/qr-code/footer_qr/4_QR_FOOTER.png)