Title: Book the Best ROMANTIC Hotels in Chestertown, NY from CA $139 - 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) ![](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # Find Romantic Hotels in Chestertown, NY from CA $139 - ![](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 [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-04&endDate=2025-11-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Chestertown Romantic Hotels ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127.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/10000000/9680000/9675100/9675030/65af6a05.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) "Very nice location. Would have enjoyed more activity like hiking or a pool or something on site. But it met our requirements for a beautiful place to stay with good food" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $329 CA $365 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/7d1b588f.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) ### 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 [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/a91c67c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Accessible (Hotel Single Queen)](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/4d6605cd.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 Glens Falls 9.4/10 Exceptional (1404) "Very clean hotel and very welcoming and nice staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zhanna [](https://www.expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![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) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/dddb7afc.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) ![Dining](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/f27894c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Bay YMCA Inn and Conference Center Silver Bay 8.8/10 Excellent (133) "Awesome place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $125 CA $139 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Silver-Bay-Hotels-Silver-Bay-Inn-And-Conference-Center.h96493210.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/ff93fb28.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 Lake George 8.4/10 Very good (1006) "Very good for family vacation, good view, clean room, definitely will be back next time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johan Des CA $142 CA $185 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Luxury Cabin, 1 Bedroom, Lake View | Living area](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/f7b9a081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Cabin, 2 Bedrooms, Non Smoking, Lake View | Private kitchen](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/e2de35ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cabin, 1 Bedroom, Lake View](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/f8528e6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trout House Village Resort Hague 9.8/10 Exceptional (17) "Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $210 CA $268 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Hague-Hotels-Trout-House-Village-Resort.h108598337.Hotel-Information) ![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/28000000/27120000/27117400/27117326/16e44dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/3afcf576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/264cd283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS North River 10/10 Exceptional (92) "I booked Camp Twosome for me and my dog to get away from everything and unplug, and that's just what we did! Beautiful mountain view, and only a short drive from 13th Lake. This trip was all about the solitude, but next time I'll try the pizza and hot tub!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobby R. CA $266 CA $383 total includes taxes & fees Nov 5 - Nov 6 [](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 CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR North River 9.2/10 Wonderful (61) "Bird Camp is nestled on a beautiful and peaceful hobby farm. The camp is well maintained and very cozy. We had a wonderful time and we are looking forward to our next stay here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zacchary B. CA $245 CA $373 total includes taxes & fees Nov 5 - Nov 6 [](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) ![Interior](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/20ec9d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/d87ef07f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/582e0488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Camp Lillian Gorgeous New Cabin with Mountain Views North River 9.8/10 Exceptional (74) "Enjoyed our stay. Had everything we needed. Quiet with beautiful view." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) steve z. CA $224 CA $330 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Lake-George-Hotels-Camp-Lillian-Gorgeous-Brand-New-Cabin-With-Mountain-Views.h48604936.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) ![Fireplace, books](https://images.trvl-media.com/lodging/20000000/19470000/19460500/19460422/4f6e3d1b.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/20000000/19470000/19460500/19460422/3c9ec132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful cottage on scenic Adirondack hobby farm North River 9.6/10 Exceptional (59) "Peaceful, lots of room, friendly dogs, nice to get away from the city. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda V. CA $245 CA $356 total includes taxes & fees Nov 5 - Nov 6 [](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=2025-11-18&endDate=2025-11-19®ionId=89045&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![The Queensbury Hotel](//images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Very clean hotel and very welcoming and nice staff." [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 "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) ![Courtyard by Marriott Lake George](//images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "The room was spotless" [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![Hampton Inn & Suites Lake George](//images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456_y.jpg) ### Hampton Inn & Suites Lake George 10/10 Excellent "Excellent breakfast. " [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![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 "Very friendly and welcoming! The view is beautiful! The room was clean and comfortable! Will definitely come again!" [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.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 "Desk Staff was very pleasant and helpful. Room was clean . " [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Scotty's Lakeside Resort](//images.trvl-media.com/lodging/11000000/10130000/10128900/10128851/0c2b60c3_y.jpg) ### Scotty's Lakeside Resort 10/10 Excellent "Place was clean and quite and easy access to town. Great staff " [](https://expedia.ca/Lake-George-Hotels-Scottys-Lakeside-Resort.h10128851.Hotel-Information) ![Baymont by Wyndham Queensbury / Lake George](//images.trvl-media.com/lodging/1000000/30000/23700/23630/cf943129_y.jpg) ### Baymont by Wyndham Queensbury / Lake George 10/10 Excellent "..." [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.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) ## Frequently asked questions ### Searching for romantic hotels in Chestertown? > If you and your partner need a romantic escape, we've got just the thing. Our guests also enjoy Chestertown for its lakeside setting. You might consider checking out some of the nearby sights and attractions such as Loon Lake Beach, Friends Lake, or Loon Lake. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Chestertown? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures 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 do in Chestertown? > There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all that Chestertown has to offer. Couples looking to get out in nature will enjoy Chestertown for its lakeside setting. If you want to spend a day exploring, you might consider a stop at Loon Lake Beach, Friends Lake, or Loon Lake. ### What's the best way to get to Chestertown and around town during my romantic getaway? > These transportation options in Chestertown might help your romantic getaway go off without a hitch: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), which is the closest major airport located 23.6 mi (38 km) from the city center. 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