Title: Book the Best BEACH RESORTS in Chestertown, NY from CA $650 - Chestertown Hotels on the Beach| 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)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d89045.Destination-Travel-Guides) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # Find beach hotels in Chestertown, NY from CA $650 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chestertown Beach Hotel Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Our top choices for Chestertown beach hotels ![Exterior](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/5e61cc3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/c57c39d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/07b9acd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/c3090534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Tree Motel & Cabins [](https://www.expedia.ca/Lake-George-Hotels-Pine-Tree-Motel-Cabins.h8355292.Hotel-Information) Chestertown 9.2/10 Wonderful (146) "Excellent location and staff was very friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Logan [](https://www.expedia.ca/Lake-George-Hotels-Pine-Tree-Motel-Cabins.h8355292.Hotel-Information) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room | Television](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/0d6c5cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/bf13d00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/541a0034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friends Lake Inn [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) Chestertown 8.6/10 Excellent (102) "Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) ![Lake view](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/ccbb7c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/c74c01f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, Hot Tub, Lake View (Birch)](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/9867809e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Fern Lodge [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) Chestertown 9.8/10 Exceptional (50) "Absolutely beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana CA $728 CA $809 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/28ce5322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/0453e0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/96e22feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/f6bed109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom [](https://www.expedia.ca/Chestertown-Hotels-Cozy-3BR-35BA-Lodge-W-Lake-Beach-Access.h119689867.Hotel-Information) Chestertown 10/10 Exceptional (3) "Rooms were very clean. Location was great, next to many hiking spots. However, far from many common stores. Was beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MiaMaria C. CA $268 CA $650 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chestertown-Hotels-Cozy-3BR-35BA-Lodge-W-Lake-Beach-Access.h119689867.Hotel-Information) ![Sun loungers](https://images.trvl-media.com/lodging/88000000/87350000/87344500/87344475/995b02d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/88000000/87350000/87344500/87344475/dd287c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87350000/87344500/87344475/791f2502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/88000000/87350000/87344500/87344475/d2b1f1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing [](https://www.expedia.ca/Chestertown-Hotels-Modern-Cabin-W-Hot-Tub-Minutes-To-Lakes-Skiing.h87344475.Hotel-Information) Chestertown 10/10 Exceptional (36) "Beautifully appointed cabin in the woods. Love the hot tub, the kitchen and the entertainment areas - " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina S. [](https://www.expedia.ca/Chestertown-Hotels-Modern-Cabin-W-Hot-Tub-Minutes-To-Lakes-Skiing.h87344475.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/3602ed4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/53d5aace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/w1200h900x75y0-57ed71c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eagles Nest at Loon Lake near Gore Mountain [](https://www.expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) Chestertown 10/10 Exceptional (113) "Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy B. [](https://www.expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/c6d64672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/ddf94951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/19d96ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/708a5896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George [](https://www.expedia.ca/Chestertown-Hotels-Unique-Adirondack-Estate-On-Hudson-River-Near-Gore-Mountain-Lake-George.h76320395.Hotel-Information) Chestertown 10/10 Exceptional (71) "We had a great, though brief stay, but loved it! The Carriage House was clean and well appointed. John was welcoming and very helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff S. [](https://www.expedia.ca/Chestertown-Hotels-Unique-Adirondack-Estate-On-Hudson-River-Near-Gore-Mountain-Lake-George.h76320395.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/78000000/77980000/77976200/77976155/d0f262aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/78000000/77980000/77976200/77976155/7ae7fe8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/78000000/77980000/77976200/77976155/w2130h1158x0y3-731d3b6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77980000/77976200/77976155/0bf51eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Lakeside Retreat with Private Beach [](https://www.expedia.ca/Chestertown-Hotels-Peaceful-Lakeside-Retreat-With-Private-Beach.h77976155.Hotel-Information) Chestertown 9.4/10 Exceptional (23) "The house and property were just what we needed to relax." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth J. [](https://www.expedia.ca/Chestertown-Hotels-Peaceful-Lakeside-Retreat-With-Private-Beach.h77976155.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/270-fc2b1aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/270-1d7679ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/5b882ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/270-58885847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elizabeth. A Guest House Near Lake George. [](https://www.expedia.ca/Chestertown-Hotels-Elizabeth-A-Guest-House-Near-Lake-George.h33955795.Hotel-Information) Chestertown 8.2/10 Very good (45) "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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis M Wilson J. [](https://www.expedia.ca/Chestertown-Hotels-Elizabeth-A-Guest-House-Near-Lake-George.h33955795.Hotel-Information) ![Beach towels](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399177/e11443d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399177/e8106190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399177/e8a6a5ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64400000/64399200/64399177/4ca4a34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 30 acre-ADK Log Cabin on Kelm Lake [](https://www.expedia.ca/Chestertown-Hotels-ADK-Log-Cabin-Living-In-The-Woods.h64399177.Hotel-Information) Warrensburg 9.6/10 Exceptional (41) "We really enjoyed this cabin and our vacation there. We will definitely be going back next year." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara F. [](https://www.expedia.ca/Chestertown-Hotels-ADK-Log-Cabin-Living-In-The-Woods.h64399177.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28®ionId=89045&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "The staff was accomodating and friendly. The room was clean. I have never had a bad stay at this hotel. Plenty of options for breakfast. This hotel is really a "home away from home" kind of place!!" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "It was it was fun " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Hampton Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456_y.jpg) ### Hampton Inn & Suites Lake George 10/10 Excellent "Very accommodating and friendly staff" [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Friendly staff, wonderful food, beautiful lake views, nice amenities. " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Best Western of Lake George](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/e1f93c73_y.jpg) ### Best Western of Lake George 10/10 Excellent "Very nice gentleman " [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) ![Lodges At Cresthaven](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/4993b753_y.jpg) ### Lodges At Cresthaven 10/10 Excellent "Great !" [](https://expedia.ca/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Everyone was so nice and welcoming Room is clean Convenient location Restaurant food was delicious " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![The Georgian Lakeside Resort](https://images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/f69be4ef_y.jpg) ### The Georgian Lakeside Resort 10/10 Excellent "The room was spotless, bed & pillows were comfortable. We arrived at night and were surprised at that great view in the morning! My teenagers appreciated the list of channels and the good wi-fi connection. We all recommend ++ " [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![The Fern Lodge](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584_y.jpg) ### The Fern Lodge 10/10 Excellent "Absolutely beautiful " [](https://expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travelers who love the beach? ### What's the best accommodation to stay near the beach in Chestertown? ### When's the best time for a beach vacation in Chestertown? ### What is there to see and do around Chestertown? ### What's the best way to get to my beach hotel in Chestertown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Beach Hotel Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Beach-Hotel.0-0-d6349269-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Cheap-Hotels.0-0-d6349269-tCheapHotels.Travel-Guide-Filter-Hotels) - 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