Title: Book the Best SHOPPING Hotels in Chestertown in 2026 | 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 # Find Shopping Hotels in Chestertown, NY from CA $116 - ![](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 Shopping Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels with shopping nearby ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/45ba61c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/ddbc1bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/48e94cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119690000/119689900/119689867/37e1ae9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly 3BR 3.5BA Lodge w/ Lake & Beach, Screened Patio, Grill, Sunroom [](https://www.expedia.ca/Chestertown-Hotels-Cozy-3BR-35BA-Lodge-W-Lake-Beach-Access.h119689867.Hotel-Information) Chestertown 10/10 Exceptional (3) "Rooms were very clean. Location was great, next to many hiking spots. However, far from many common stores. Was beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MiaMaria C. CA $268 CA $652 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Chestertown-Hotels-Cozy-3BR-35BA-Lodge-W-Lake-Beach-Access.h119689867.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/30000/26400/26327/b39bcc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/30000/26400/26327/cf6fcd4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26400/26327/866894ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26400/26327/2ad8e21c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn & Suites at the Outlets of Lake George [](https://www.expedia.ca/Lake-George-Hotels-Clarion-Inn-Suites-At-The-Outlets-Of-Lake-George.h26327.Hotel-Information) Lake George 8.4/10 Very good (1004) "Clean and staff was nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal CA $104 CA $116 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lake-George-Hotels-Clarion-Inn-Suites-At-The-Outlets-Of-Lake-George.h26327.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/e8c3fc23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/453a58c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water park](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/a8a5ec23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Six Flags Great Escape Lodge & Indoor Waterpark [](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) Queensbury 7.8/10 Good (1418) "Staff are super friendly, and there are many things to do at the hotel to have fun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdiel CA $209 CA $232 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/1e1c1bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/18e42197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/291c40b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/4afbc93c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome! [](https://www.expedia.ca/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.Hotel-Information) Fort Ann 10/10 Exceptional (24) "Satisfied. Quiet and relaxing property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy F. CA $274 CA $524 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/64000000/63360000/63358600/63358578/9629ebb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63360000/63358600/63358578/fdbb7e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/64000000/63360000/63358600/63358578/5237be9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63360000/63358600/63358578/520e60a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adirondack Bungalow Getaway [](https://www.expedia.ca/Lake-George-Hotels-Adirondack-Bungalow-Getaway.h63358578.Hotel-Information) Warrensburg 10/10 Exceptional (69) "Great spot " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter R. CA $135 CA $267 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Lake-George-Hotels-Adirondack-Bungalow-Getaway.h63358578.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74120000/74116800/74116766/e6560c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74120000/74116800/74116766/fb713851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74120000/74116800/74116766/60af9f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74120000/74116800/74116766/e3cb48b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous mountain views and private! [](https://www.expedia.ca/North-River-Hotels-Gorgeous-Mountain-Views-And-Private.h74116766.Hotel-Information) North River 10/10 Exceptional (35) "We enjoyed our stay very much. A little slice of heaven. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $227 CA $330 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/North-River-Hotels-Gorgeous-Mountain-Views-And-Private.h74116766.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/93000000/92710000/92703400/92703336/1c8fbed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92710000/92703400/92703336/10f11d16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/93000000/92710000/92703400/92703336/58512616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92710000/92703400/92703336/23a90e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Superb Nature Lodge 5mns to Gore Mountain w/Large Hot Tub, Firepit & Fireplace! [](https://www.expedia.ca/North-Creek-Hotels-NEWLY-Renovated-LodgeElevated-Designed-Interiors.h92703336.Hotel-Information) Chester 10/10 Exceptional (10) "Great house for a ski weekend at Gore mountain. Very close to the slopes, and the house is beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samir R. CA $303 CA $844 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/North-Creek-Hotels-NEWLY-Renovated-LodgeElevated-Designed-Interiors.h92703336.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161475/92b15335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161475/da0758c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161475/4bc4fb07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110170000/110161500/110161475/a1483d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls [](https://www.expedia.ca/Glens-Falls-Hotels-Charming-Ground-Floor-2-Bedroom-Apartment-With-WiFi.h110161475.Hotel-Information) Glens Falls 6.4/10 (5) "Very large with everything we needed.Fast communication.We enjoyed our stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mathieu T. CA $124 CA $508 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Glens-Falls-Hotels-Charming-Ground-Floor-2-Bedroom-Apartment-With-WiFi.h110161475.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/9055a494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/97d18ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/c7efaf76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30330000/30326600/30326566/656397e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious ADK 5BR Lodge, Sleeps 14, Near Gore, Firepit, Fireplace, Pets [](https://www.expedia.ca/Wevertown-Hotels-Dog-Friendly-Family-Retreat-Cabin-WGore-Mt-Views.h30326566.Hotel-Information) North Creek 10/10 Exceptional (29) "Lots of room and beautiful cabin" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa M. CA $558 CA $1,327 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Wevertown-Hotels-Dog-Friendly-Family-Retreat-Cabin-WGore-Mt-Views.h30326566.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122070000/122062400/122062350/4d9f60d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122070000/122062400/122062350/9fd60c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122070000/122062400/122062350/26459554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122070000/122062400/122062350/97de0bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Chic Loft I - Civic Center/Cafe/Brewery/Farmers Market - Center of Town [](https://www.expedia.ca/Glens-Falls-Hotels-Luxury-Chic-Loft-I-Civic-CenterCafeBreweryFarmers-Market-Center-Of-Town.h122062350.Hotel-Information) Glens Falls CA $233 CA $560 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Glens-Falls-Hotels-Luxury-Chic-Loft-I-Civic-CenterCafeBreweryFarmers-Market-Center-Of-Town.h122062350.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=2026-01-01&endDate=2026-01-02®ionId=89045&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![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 "Clean everything " [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "The boys had a great time in the room and in the water park " [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Staff was great, the room was very clean and the price was competitive with other area hotels." [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.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 staff was accomodating and friendly. The room was clean. I have never had a bad stay at this hotel. Plenty of options for breakfast. This hotel is really a "home away from home" kind of place!!" [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.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 "Everything was great" [](https://expedia.ca/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![Super 8 by Wyndham Lake George/Warrensburg Area](https://images.trvl-media.com/lodging/1000000/460000/459800/459792/a069ae03_y.jpg) ### Super 8 by Wyndham Lake George/Warrensburg Area 10/10 Excellent "Stayed here several times. Tried other properties around the Warrensburg area but keep coming back. It is an excellent value - clean, safe, affordable." [](https://expedia.ca/Lake-George-Hotels-Super-8-By-Wyndham-Lake-GeorgeWarrensburg-Area.h459792.Hotel-Information) ![Best Western of Lake George](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/e1f93c73_y.jpg) ### Best Western of Lake George 10/10 Excellent "Very nice gentleman " [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.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 "Everyone was so nice and welcoming Room is clean Convenient location Restaurant food was delicious " [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![The Georgian Lakeside Resort](https://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) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [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) - [Historic Hotels in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Historic-Hotel.0-0-d6349269-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Adirondack ](https://www.expedia.ca/Adirondack-Hotels-Hotel-With-Pool.0-0-d6349269-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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