Title: Book the Best ROMANTIC Hotels in Chestertown, NY from CA $327 - 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 $327 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-26&endDate=2025-09-27&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-27&endDate=2025-09-28&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-26&endDate=2025-09-28&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-03&endDate=2025-10-05&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) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3a2c4196.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) ### Friends Lake Inn Chestertown 8.8/10 Excellent (101) "Staff was great. The inn is unique. Perfect!" CA $295 CA $327 total includes taxes & fees Sep 29 - Sep 30 [](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/2000000/1540000/1539000/1538972/7d1b588f.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 (47) "We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer." CA $737 CA $819 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.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=2025-10-11&endDate=2025-10-12®ionId=89045&adults=2&travelerType=romantic&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 "The accommodations were amazing, and the grounds were beautiful." [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.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 bed was very comfortable and the room was clean." [](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 "Facility as a whole appears new. Very clean everywhere. Pool and hot tub were great. Restaurant and bar were busy and service was great. Rooms were very comfortable." [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.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 "Very good price for location." [](https://expedia.ca/Lake-George-Hotels-Baymont-By-Wyndham-Queensbury-Lake-George.h23630.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 "Property was very nice and clean Staff in the lunch area was rude and unfriendly actually left the restaurant without being served " [](https://expedia.ca/Lake-George-Hotels-The-Georgian-Lakeside-Resort.h1194009.Hotel-Information) ![The Queensbury Hotel](//images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "I liked everything about the queensbury " [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 "We’ve stayed here a number of times over the past several years attending various events in the area..Have always found it to be clean and quiet. Everything always works as it should. Staff are always pleasant and helpful. Cost is not unreasonable for the area. We have no reason to look elsewhere.. " [](https://expedia.ca/Lake-George-Hotels-Comfort-Inn-Suites.h1640103.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 scenery and the amenities were amazing, with the breakfast and goodie bag were a great surprise." [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Tiki Resort](//images.trvl-media.com/lodging/1000000/50000/43200/43183/5068bb33_y.jpg) ### Tiki Resort 10/10 Excellent "We were happy with the accessibility to the room since my husband is handicapped. It had a nice walk-in shower. Considering the age of the property, it is in good shape! We also appreciated the breakfast cafe, the food was fast, good and reasonably priced. I would definitely stay there again!" [](https://expedia.ca/Lake-George-Hotels-Tiki-Resort.h43183.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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