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 [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-11&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-12&endDate=2025-10-13&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## 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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/0a784cce.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) ![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) ### Friends Lake Inn Chestertown 8.6/10 Excellent (102) "Staff was great. The inn is unique. Perfect!" CA $296 CA $329 total includes taxes & fees Oct 13 - Oct 14 [](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) ![Interior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/698049bb.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) ![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 (47) "Comfortable, friendly, beautiful lodge, spacious facilities" CA $710 CA $789 total includes taxes & fees Nov 11 - Nov 12 [](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) ![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) ![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) ### The Queensbury Hotel Glens Falls 9.4/10 Exceptional (1379) "Great place to stay. " CA $131 CA $146 total includes taxes & fees Oct 30 - Oct 31 [](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) ![Dining](https://images.trvl-media.com/lodging/97000000/96500000/96493300/96493210/0c7cc18a.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/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 (125) "Awesome place" CA $125 CA $139 total includes taxes & fees Oct 20 - Oct 21 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/ff93fb28.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) "a very nice place to stay" CA $142 CA $185 total includes taxes & fees Nov 5 - Nov 6 [](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) ![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) ### 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." CA $164 CA $217 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hague-Hotels-Trout-House-Village-Resort.h108598337.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/20000000/19400000/19394100/19394051/259d0ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19400000/19394100/19394051/20031a02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19400000/19394100/19394051/8e52bdc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19400000/19394100/19394051/a1708f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### GLAMP RICHARD ON ADIRONDACK FLOWER FARM North River 9.4/10 Exceptional (20) "Leslie is a wonderful person and host. Very caring. I look forward to bringing my 80 year old mom. Leslie pizza is awesome. The entire experience was one of my favorite stays in the Adirondacks. If your looking for a peaceful and beautiful stay dont pass this opportunity up!" CA $167 CA $232 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Lake-George-Hotels-Canvas-Cabin-ON-Pretty-Farm.h19394051.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/20000000/19500000/19499300/19499232/eb5fc9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19500000/19499300/19499232/b68c0847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/20000000/19500000/19499300/19499232/6857b514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19500000/19499300/19499232/5673e62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM North River 9.8/10 Exceptional (40) "We loved our stay! The property is amazing and the hosts were wonderful. We enjoyed the brick oven pizza and the sweet dogs. We will absolutely be back!" CA $181 CA $247 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/North-River-Hotels-GLAMP-BERNICE-ON-BEAUTIFUL-ADIRONDACK-HOBBY-FARM.h19499232.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/096c96c2.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) ### ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS North River 10/10 Exceptional (91) "Great location beautiful view and very nice cabin thank you!" CA $266 CA $381 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Lake-George-Hotels-Adorable-NEW-Cabin-With-Amazing-Mountain-Views.h27117326.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) ![Dining](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/891b218c.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) ### Camp Lillian Gorgeous New Cabin with Mountain Views North River 9.8/10 Exceptional (74) "The Lillian cabin was great!! It was not only beautifully made but it had everything we needed including a peaceful and quiet two nights in the Adirondacks!!" CA $224 CA $330 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lake-George-Hotels-Camp-Lillian-Gorgeous-Brand-New-Cabin-With-Mountain-Views.h48604936.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=2025-10-25&endDate=2025-10-26®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 "Old hotel remodeled Very nice" [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 "It was an grat place to stay" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 " Friendly staff" [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.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 "Nice stay!" [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.Hotel-Information) ![Tiki Resort](//images.trvl-media.com/lodging/1000000/50000/43200/43183/5068bb33_y.jpg) ### Tiki Resort 10/10 Excellent "The parking is great and only a few blocks to town" [](https://expedia.ca/Lake-George-Hotels-Tiki-Resort.h43183.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 "Clean rooms and helpful staff " [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.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 "Hotel is very nice, the staff as well! The hotel is very clean, lots do do, and the facility was beautufil" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.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 "Very clean room the staff also very helpful may you feel like you are part of the family " [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.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 ### 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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