Title: Book the Best ROMANTIC Hotels in Chestertown, NY from CA $153 - Chestertown Romantic Getaways | 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 ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Romantic Hotels Tonight [Feb 13 - Feb 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-02-13&endDate=2026-02-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Feb 14 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-02-14&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Chestertown romantic hotels ![Lake view](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Hot Tub, Lake View (Forest)](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/0c9e1948.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) ### The Fern Lodge [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) Chestertown 10/10 Exceptional (52 reviews) "I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Morgan [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/72d8a398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/0c7cc18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, Multiple Beds, Lake View | Courtyard view](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/f0bfc238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach volleyball, sailing, kayaking](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/9205018c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Bay YMCA Inn and Conference Center [](https://www.expedia.ca/Silver-Bay-Hotels-Silver-Bay-Inn-And-Conference-Center.h96493210.Hotel-Information) Silver Bay 8.8/10 Excellent (138 reviews) "Yes but wished they had tv’s" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina CA $138 CA $153 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Silver-Bay-Hotels-Silver-Bay-Inn-And-Conference-Center.h96493210.Hotel-Information) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/2f07bb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Hotel Double Queen Bed)](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/d17a446d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/75b79163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/01f531cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Queensbury Hotel [](https://www.expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) Glens Falls 9.4/10 Exceptional (1,509 reviews) "everything was great very quiet room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) patrick [](https://www.expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/8b8d1fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/3dd62919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/59b5e6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/7c36798c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fort William Henry Hotel and Conference Center [](https://www.expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) Lake George 8.4/10 Very good (1,002 reviews) "Friendly staff, immaculate hotel and always a lot of fun!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giuliana CA $161 CA $205 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Cabin, 1 Bedroom, Non Smoking, Lake View](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/f9b80062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/c1a259a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/ca48d4b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cabin, 1 Bedroom, Lake View | Living area](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/a86c9135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trout House Village Resort [](https://www.expedia.ca/Hague-Hotels-Trout-House-Village-Resort.h108598337.Hotel-Information) Hague 9.8/10 Exceptional (22 reviews) "Great updated cabin. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $292 CA $358 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Hague-Hotels-Trout-House-Village-Resort.h108598337.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/16e44dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/5162aed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/fe15abca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/096c96c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT [](https://www.expedia.ca/Lake-George-Hotels-Adorable-NEW-Cabin-With-Amazing-Mountain-Views.h27117326.Hotel-Information) North River 10/10 Exceptional (95 reviews) "Cabin was very well done, clean- bed was super comfortable! The view of the mountains was fantastic- great for star watching too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) millie h. CA $225 CA $328 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lake-George-Hotels-Adorable-NEW-Cabin-With-Amazing-Mountain-Views.h27117326.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/7332418d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/1162c961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/3f8eb4f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19320000/19318000/19317908/75cc202b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS [](https://www.expedia.ca/Lake-George-Hotels-Restored-Historic-Adirondack-Camp-Views-OF-Nearby-Gore-Moutain.h19317908.Hotel-Information) North River 9.2/10 Wonderful (65 reviews) "See you next year amazing stay great food loved the bird camp cabin—- Brian, Darlene, Gracie and Hayden " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian W. CA $238 CA $363 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lake-George-Hotels-Restored-Historic-Adirondack-Camp-Views-OF-Nearby-Gore-Moutain.h19317908.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/ad48000a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/42db7255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/20ec9d4a_edited_1a0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/891b218c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Camp Lillian Gorgeous New Cabin with Mountain Views [](https://www.expedia.ca/Lake-George-Hotels-Camp-Lillian-Gorgeous-Brand-New-Cabin-With-Mountain-Views.h48604936.Hotel-Information) North River 9.8/10 Exceptional (78 reviews) "Just what we were looking for. Beautiful and peaceful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa S. CA $225 CA $328 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lake-George-Hotels-Camp-Lillian-Gorgeous-Brand-New-Cabin-With-Mountain-Views.h48604936.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/ae0170a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/w1942h1650x4y0-5f8d2d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/1c7fdb4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/f9857ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Handcrafted mountain cabin with gorgeous views [](https://www.expedia.ca/Lake-George-Hotels-Handcrafted-Mountain-Cabin-With-Gorgeous-Views.h62969907.Hotel-Information) North River 9.8/10 Exceptional (49 reviews) "This spot was ideal for us. Beauty, privacy, quiet, comfort. We used it as a base camp for exploring the Adirondacks. Felt remote but nearby North Creek had everything we needed. We had glorious weather and were outside most of the time, but the cabin was big enough for reading and playing games if we had needed to be inside more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna T. CA $231 CA $337 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/Lake-George-Hotels-Handcrafted-Mountain-Cabin-With-Gorgeous-Views.h62969907.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/20000000/19470000/19460500/19460422/2495f744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19470000/19460500/19460422/6ba96c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19470000/19460500/19460422/w2592h1656x0y72-18d56d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/20000000/19470000/19460500/19460422/af9cdb51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful cottage on scenic Adirondack hobby farm [](https://www.expedia.ca/Lake-George-Hotels-Beautiful-Cottage-On-Scenic-Adirondack-Hobby-Farm.h19460422.Hotel-Information) North River 9.6/10 Exceptional (61 reviews) "This place was great! We enjoyed walking the property and hot tubbing. The farmhouse was unique, but amazing! Leslie and team were friendly, we enjoyed chats over breakfast and pizza. Would definitely visit again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake W. CA $204 CA $302 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lake-George-Hotels-Beautiful-Cottage-On-Scenic-Adirondack-Hobby-Farm.h19460422.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=2026-02-28&endDate=2026-03-01®ionId=89045&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_89045) ## Top Chestertown Hotel Reviews ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "everything was great very quiet room" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 "Everything stood out! This was honestly a very wonderful hotel experience for us, and we stay at a lot of hotels throughout the year. Highlights: Our room was spotless. The staff was incredibly nice. The breakfast offered a lot of variety. Our family really enjoyed the pool and hot tub as well." [](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 "Clean rooms, very courteous staff, beautiful property and fun environment " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Courtyard by Marriott Lake George](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "Room was great, staff is great, second time at this hotel and it was consistent with the first stay!! Highly recommend" [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![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 room was spotless" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 "Great relaxed vibe. Nice room and nice common places. " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Comfort Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1650000/1640200/1640103/93d3500a_y.jpg) ### Comfort Inn & Suites Lake George 10/10 Excellent "Great stay, we were able to check-in about 45 mins early. There were ice bars at some local hotels and s brewery. Easy walk, wonderful night in Lake George. " [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information) ![The Fern Lodge](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584_y.jpg) ### The Fern Lodge 10/10 Excellent "I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! " [](https://expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chestertown? ### When is the best time of year for a romantic getaway to Chestertown? ### What is there to do in Chestertown? ### What's the best way to get to Chestertown and around town during my romantic getaway? ## 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) - [Family Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Family-Hotel.0-0-d6349269-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Golf-Hotel.0-0-d6349269-tGolfHotel.Travel-Guide-Filter-Hotels) - 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