Title: Book the Best BEACH RESORTS in Chestertown, NY from CA $401 - 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) ![](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # Find beach hotels in Chestertown, NY from CA $401 ![](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 [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Top Chestertown Beach Hotel ![Exterior](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/29c27732.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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/55c4d212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8360000/8355300/8355292/8220a41e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Tree Motel & Cabins Chestertown 9.2/10 Wonderful (144) "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/10000000/9680000/9675100/9675030/8bdcc127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/1b13c3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3a2c4196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friends Lake Inn Chestertown 8.6/10 Excellent (102) "Staff was great. The inn is unique. Perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $361 CA $401 total includes taxes & fees Nov 7 - Nov 8 [](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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/4c20fc37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/698049bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Double Room, Hot Tub, Lake View (Oak)](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/52ace6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Fern Lodge Chestertown 9.8/10 Exceptional (49) "Comfortable, friendly, beautiful lodge, spacious facilities" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Frederick CA $602 CA $668 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.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) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/88000000/87350000/87344500/87344475/7ab04e7c.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 Chestertown 10/10 Exceptional (35) "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) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/45ba61c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/48e94cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/ddbc1bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/37e1ae9a.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 Chestertown 10/10 Exceptional (1) "Very comfortable!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim K. CA $239 CA $658 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chestertown-Hotels-Cozy-3BR-35BA-Lodge-W-Lake-Beach-Access.h119689867.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) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/87350c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/1633467d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/d1a5831f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown 10/10 Exceptional (113) "This is the second time that our family has stayed at Eagle's Nest. We enjoyed our time together once again. We had plenty of room and the fire pit, game room and games, sand box and canoes/kayaks were a welcome addition once again. We love the area and this home accommodates our family nicely." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pam R. [](https://www.expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/270-a9c2da06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/84a0f817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/68b8b714.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. Chestertown 8.2/10 Very good (45) "Great place to celebrate with large family" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan C. [](https://www.expedia.ca/Chestertown-Hotels-Elizabeth-A-Guest-House-Near-Lake-George.h33955795.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) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/d5e7281e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/b59836f3.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 Chestertown 10/10 Exceptional (71) "My family and i had a great time here! The place is Amazing and we would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer D. [](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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77976200/77976155/e1a1157f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77980000/77976200/77976155/68dfbaa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Lakeside Retreat with Private Beach 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) ![On the beach](https://images.trvl-media.com/lodging/46000000/45870000/45865700/45865607/1c3590dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45870000/45865700/45865607/ff8c693b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/46000000/45870000/45865700/45865607/31d5bbda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45870000/45865700/45865607/c1cb3d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! Chestertown 9.4/10 Exceptional (18) "The views were absolutely amazing! We will definitely be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather [](https://www.expedia.ca/Chestertown-Hotels-4-Adirondack-FamilyFriendly-Waterfront-On-LoonLake-Boating.h45865607.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=2025-11-11&endDate=2025-11-12®ionId=89045&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![Fort William Henry Hotel and Conference Center](//images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Beautiful area, nice room" [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![The Georgian Lakeside Resort](//images.trvl-media.com/lodging/2000000/1200000/1194100/1194009/f69be4ef_y.jpg) ### The Georgian Lakeside Resort 10/10 Excellent "we enjoyed the happy hour with a glass of wine and a beer with nachos. Food was great. I would have enjoyed the wine more if it was in a glass, vs a plastic cup. Service was great and the staff was friendly." [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![Comfort Inn & Suites Lake George](//images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg) ### Comfort Inn & Suites Lake George 10/10 Excellent "Clean and not crowded, went offseason and almost Empty! Little dated but huge rooms and everything you needed plus breakfast, win-win. I’d go back" [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information) ![Six Flags Great Escape Lodge & Indoor Waterpark](//images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "Clean, staff was super friendly and accommodating for children " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Clarion Inn & Suites at the Outlets of Lake George](//images.trvl-media.com/lodging/1000000/30000/26400/26327/b39bcc22_y.jpg) ### Clarion Inn & Suites at the Outlets of Lake George 10/10 Excellent "Hotel was maintained and kept in good shape for being an older place." [](https://expedia.ca/Lake-George-Hotels-Clarion-Inn-Suites-At-The-Outlets-Of-Lake-George.h26327.Hotel-Information) ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](//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 excellent. The room was immaculate. Overall, a great stay." [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](//images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Bar and restaurant on site, walkable to the village area" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Best Western of Lake George](//images.trvl-media.com/lodging/1000000/30000/25000/24945/e1f93c73_y.jpg) ### Best Western of Lake George 10/10 Excellent "Facility was mostly clean, looked a little aged exterior and interior. Room was good. Place was quiet, no thin walls. There was only one towel per person, no wash clothes or hand towels...." [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information) ![Friends Lake Inn](//images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127_y.jpg) ### Friends Lake Inn 10/10 Excellent "Staff was great. The inn is unique. Perfect!" [](https://expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travelers who love the beach? > Known for its lakeside setting, Chestertown offers a lot for the traveler planning a getaway. ### What's the best accommodation to stay near the beach in Chestertown? > [The Fern Lodge](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach. ### When's the best time for a beach vacation in Chestertown? > Plan your trip to the beach with a look at the seasons in Chestertown: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall. ### What is there to see and do around Chestertown? > After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Rogers Memorial Park Beach or Veterans Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions like Loon Lake Beach and Friends Lake. Other things to see and do in the area are Loon Lake and Hudson River. ### What's the best way to get to my beach hotel in Chestertown? > Here's some information to help you get to and around your beach accommodation in Chestertown more easily: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest major airport which is located 23.6 mi (38 km) from the city center. 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