Title: Book the Best ROMANTIC Hotels in Chester Shores, Chestertown from CA $139 - Chester Shores Romantic Getaways | Expedia.ca [Chester Shores Travel Guide](https://expedia.ca/Chestertown-Chester-Shores.dx553248635976471458)[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)[Chester Shores Car Rentals](https://expedia.ca/Car-Rentals-In-Chester-Shores.d553248635976471458.Car-Rental-Guide)[Chester Shores Vacations](https://expedia.ca/Chester-Shores.d553248635976471458.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/romantic.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Chester Shores, Chestertown 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 Chester Shores Romantic Hotels Tonight [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976471458&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976471458&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471458&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976471458&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Chester Shores Romantic Hotels ![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) ![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) ![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) ### Silver Bay YMCA Inn and Conference Center Silver Bay 8.8/10 Excellent (130) "Awesome place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $125 CA $139 total includes taxes & fees Oct 28 - Oct 29 [](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) ![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) ![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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) william CA $143 CA $186 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) ![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) ![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) ![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) ### 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 $209 CA $267 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Hague-Hotels-Trout-House-Village-Resort.h108598337.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/10000000/9680000/9675100/9675030/3a2c4196.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) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.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 $333 CA $370 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19500000/19499300/19499232/b68c0847.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 (41) "Been here several times and happily keep going back. Such an amazing niche this place is. We also kayaked on 13th lake while here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise K. CA $181 CA $247 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/North-River-Hotels-GLAMP-BERNICE-ON-BEAUTIFUL-ADIRONDACK-HOBBY-FARM.h19499232.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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19470000/19460500/19460422/3c9ec132.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/20000000/19470000/19460500/19460422/3d73ec71.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) "A really wonderful place to stay! The farm is so beautiful and quiet. Our host was so nice and accommodating. The breakfast was great as was the pizza. We felt really at home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joelle D. CA $245 CA $356 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lake-George-Hotels-Beautiful-Cottage-On-Scenic-Adirondack-Hobby-Farm.h19460422.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) ![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) ![Interior](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/698049bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Fern Lodge Chestertown 9.8/10 Exceptional (49) "Absolutely beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana CA $602 CA $668 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.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) ![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117400/27117326/3afcf576.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) ![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 NEW CABIN WITH AMAZING MOUNTAIN VIEWS North River 10/10 Exceptional (92) "Great location beautiful view and very nice cabin thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aline B. CA $266 CA $382 total includes taxes & fees Oct 28 - Oct 29 [](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) ![Exterior](https://images.trvl-media.com/lodging/49000000/48610000/48605000/48604936/582e0488.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) ![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!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert CA $224 CA $329 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) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/43be1dbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/ae0170a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/2f9571b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/63000000/62970000/62970000/62969907/ed511d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Handcrafted mountain cabin with gorgeous views North River 9.8/10 Exceptional (49) "Lovely little cabin tucked away near many hiking trails and the cute town of North Creek. Thanks so much!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aileen T. CA $245 CA $356 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lake-George-Hotels-Handcrafted-Mountain-Cabin-With-Gorgeous-Views.h62969907.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=2025-11-10&endDate=2025-11-11®ionId=553248635976471458&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Shores 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 "Located on the lake ( exellent view ) clean room and grounds. This place has breakfast lunch and dinner in a glass enclosed dining room facing the lake . All around nice experiance." [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.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 "Clean room" [](https://expedia.ca/Lake-George-Hotels-Scottys-Lakeside-Resort.h10128851.Hotel-Information) ![Tiki Resort](//images.trvl-media.com/lodging/1000000/50000/43200/43183/047b29fd_y.jpg) ### Tiki Resort 10/10 Excellent "Room was clean, location is great, staff was friendly! " [](https://expedia.ca/Lake-George-Hotels-Tiki-Resort.h43183.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 "Great times!" [](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 "Room was very clean and spacious! " [](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 "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 Chester Shores? > Are you and your partner looking for a romantic getaway? If you want to see some of the sights in Chester Shores, you might consider checking out Loon Lake. If you'd like to stay close to a particular destination, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list. ### What is there to do in Chester Shores? > There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Chester Shores has to offer. 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