Title: Chestertown Vacation Home Rentals from CA $262: Search Top Private Vacation Homes for Rent | 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 ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown vacation homes ![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/w1200h900x75y0-57ed71c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/53d5aace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/d25fd886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) 10/10 Exceptional (115 reviews) "Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy B. CA $342 CA $955 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/bb79f891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/05207c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/ac64b77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18955400/18955323/45b2aa6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chestertown [](https://www.expedia.ca/Chestertown-Hotels-The-Lily-Pad-At-Loon-Lake-Near-Gore-Mountain.h18955323.Hotel-Information) 9.6/10 Exceptional (40 reviews) "Comfortable stay with extended family. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pam V. CA $246 CA $656 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Chestertown-Hotels-The-Lily-Pad-At-Loon-Lake-Near-Gore-Mountain.h18955323.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/102000000/101930000/101920800/101920709/f7b53c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/102000000/101930000/101920800/101920709/bf8ad892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101930000/101920800/101920709/4d110468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101930000/101920800/101920709/bddb30cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lake Luzerene [](https://www.expedia.ca/Lake-Luzerne-Hotels-Vacation-Cabin-Just-Minutes-From-Lake-George.h101920709.Hotel-Information) 10/10 Exceptional (13 reviews) "This was our second time staying at Potash Road. Just like the first time, it was a wonderful experience. We will definitely be booking here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurie S. CA $239 CA $645 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Lake-Luzerne-Hotels-Vacation-Cabin-Just-Minutes-From-Lake-George.h101920709.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/113000000/112210000/112205500/112205437/bbb23942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112210000/112205500/112205437/9eca2902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112210000/112205500/112205437/7f606db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112210000/112205500/112205437/830e7415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Diamond Point [](https://www.expedia.ca/Diamond-Point-Hotels-True-Adirondack-Living-3-Bedroom-House-In-Tranquil-Diamond-Point.h112205437.Hotel-Information) 10/10 Exceptional (9 reviews) "Fantastic stay. Clean and welcoming. Plenty of staples supplied which is always helpful. Will visit again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brad S. CA $477 CA $952 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Diamond-Point-Hotels-True-Adirondack-Living-3-Bedroom-House-In-Tranquil-Diamond-Point.h112205437.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117330000/117325000/117324923/ee842935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117330000/117325000/117324923/8eea5b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117330000/117325000/117324923/c20ef3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/118000000/117330000/117325000/117324923/e55b4daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Olmstedville [](https://www.expedia.ca/Olmstedville-Hotels-NEW-10-Mi-To-Gore-Mountain-Home-In-Adirondack-Park.h117324923.Hotel-Information) 10/10 Exceptional (8 reviews) "Exactly what we needed & was stocked with great games, cooking supplies & blankets! Can’t wait to come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katlyn H. CA $331 CA $1,103 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Olmstedville-Hotels-NEW-10-Mi-To-Gore-Mountain-Home-In-Adirondack-Park.h117324923.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63360000/63358600/63358578/fdbb7e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63360000/63358600/63358578/9629ebb2.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) ### Vacation Home in Warrensburg [](https://www.expedia.ca/Lake-George-Hotels-Adirondack-Bungalow-Getaway.h63358578.Hotel-Information) 10/10 Exceptional (71 reviews) "Great spot " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Winter R. CA $134 CA $262 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Lake-George-Hotels-Adirondack-Bungalow-Getaway.h63358578.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94280000/94272300/94272230/w1080h1920x0y210-4dc17d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/95000000/94280000/94272300/94272230/w1080h2235x0y32-8c432e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/95000000/94280000/94272300/94272230/w1080h2302x0y16-23083199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94280000/94272300/94272230/bdd4bb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Minerva [](https://www.expedia.ca/Minerva-Hotels-Yurt-Red-Arrow.h94272230.Hotel-Information) 10/10 Exceptional (1 review) "Absolutely fantastic! Hosts were very kind and responsive. Property was clean and cozy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine T. CA $171 CA $351 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Minerva-Hotels-Yurt-Red-Arrow.h94272230.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/127000000/126170000/126161800/126161782/f473c04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/127000000/126170000/126161800/126161782/03d0f5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126170000/126161800/126161782/0bc8f1c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/127000000/126170000/126161800/126161782/2cd553c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in North Creek [](https://www.expedia.ca/North-Creek-Hotels-Lovely-3-Bedroom-House-Close-To-Gore-Mountain-For-Skiing.h126161782.Hotel-Information) 10/10 Exceptional (1 review) "Brittany was super responsive and welcoming. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) dana c. CA $285 CA $619 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/North-Creek-Hotels-Lovely-3-Bedroom-House-Close-To-Gore-Mountain-For-Skiing.h126161782.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/20000000/19320000/19317900/19317842/2142784c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19320000/19317900/19317842/c8919bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19320000/19317900/19317842/055d4e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19320000/19317900/19317842/64f38433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in North River [](https://www.expedia.ca/Lake-George-Hotels-Sweet-New-Cabin-With-Amazing-Views-Of-The-Hudson-River.h19317842.Hotel-Information) 9.8/10 Exceptional (42 reviews) "The place was as charming as the pictures, and the views were incredible. We would also recommend the bath/hot tub as well, it was a relaxing and lovely stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer A. CA $198 CA $289 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Lake-George-Hotels-Sweet-New-Cabin-With-Amazing-Views-Of-The-Hudson-River.h19317842.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92600000/92595000/92594929/14f10175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/93000000/92600000/92595000/92594929/cee21dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92600000/92595000/92594929/707a6bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92600000/92595000/92594929/66bcc962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Glens Falls [](https://www.expedia.ca/Glens-Falls-Hotels-Spectacular-Roof-Top-Patio-3bd-Apartment-In-Downtown-Glens-Falls.h92594929.Hotel-Information) 10/10 Exceptional (7 reviews) "Everything was exactly as advertised, wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim W. CA $750 CA $1,254 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Glens-Falls-Hotels-Spectacular-Roof-Top-Patio-3bd-Apartment-In-Downtown-Glens-Falls.h92594929.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104210000/104203100/104203071/10e120eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104210000/104203100/104203071/41d679a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/105000000/104210000/104203100/104203071/e3010560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/105000000/104210000/104203100/104203071/06bb513a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lake George [](https://www.expedia.ca/Lake-George-Hotels-Three-Bedroom-House-Lake-George.h104203071.Hotel-Information) 8.0/10 Very good (1 review) "This is a neat, small house, that while a bit dated in decor, was very comfortable and clean for an overnight reunion of "senior" friends from high school. It provided us with the space to sit and reminisce and catch up on each other's lives. There was a nice deck overlooking a small picturesque stream, a large, comfortable living room and an adequate kitchen that met our needs. There is also a pool, which, being late in September was not open, but is a nice bonus in season, as well as an... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan T. CA $203 CA $307 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Lake-George-Hotels-Three-Bedroom-House-Lake-George.h104203071.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/103000000/102190000/102189000/102188933/0ea49ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102190000/102189000/102188933/908cdbff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/103000000/102190000/102189000/102188933/f7fd5c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102190000/102189000/102188933/98234993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lake George [](https://www.expedia.ca/Lake-George-Hotels-Luxurious-Lake-George-Getaway.h102188933.Hotel-Information) 9.8/10 Exceptional (12 reviews) "Beautiful place, host was awesome in all communications. Great place will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne E. CA $513 CA $1,153 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Lake-George-Hotels-Luxurious-Lake-George-Getaway.h102188933.Hotel-Information) ![House, 5 Bedrooms | Exterior](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/ba3ba704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Interior](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/b23b4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Interior](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/c187e462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 5 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/448c2500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Olmstedville [](https://www.expedia.ca/Olmstedville-Hotels-10-Mi-To-Gore-Mountain-Home-In-Adirondack-Park-5-Bedroom-Home.h117320619.Hotel-Information) CA $329 CA $1,128 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Olmstedville-Hotels-10-Mi-To-Gore-Mountain-Home-In-Adirondack-Park-5-Bedroom-Home.h117320619.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=2026-03-17&endDate=2026-03-18®ionId=89045&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_89045) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APART_HOTEL) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CHALET) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America®ionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VILLA) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Private-Vacation-Homes.d89045-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Private-Vacation-Homes.d89045-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![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 "Room was nice, clean!!" [](https://expedia.ca/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.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 "Room was clean, brought our extra pillows up quickly!" [](https://expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.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 "Free breakfast nice ! " [](https://expedia.ca/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![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 "Nice comfy bed. Warm hot tub. Clean. Friendly staff. Will be staying again" [](https://expedia.ca/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.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 "We've stayed here before, we ski and it is less then 30 min from the mountain. It is always quiet and clean. The staff is friendly." [](https://expedia.ca/Lake-George-Hotels-Super-8-By-Wyndham-Lake-GeorgeWarrensburg-Area.h459792.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lake George](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/4b0bd02a_y.jpg) ### La Quinta Inn & Suites by Wyndham Lake George 2/10 Terrible "The room was ok ish staff was ok lots of noise and no towels in the pool area and wet floors everywhere place kinda run down " [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/8795775f_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Excellent hotel with great breakfast" [](https://expedia.ca/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/8b8d1fb3_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Large rooms, very clean and great location " [](https://expedia.ca/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 6/10 Okay "Staff good Room really small Bathroom toliet extremely low to the floor Only 2 plugs in whole room Mattress not comfortable " [](https://expedia.ca/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ## Find out more about Chestertown ## Chestertown Vacation Homes information | Number of reviews | 311 | | ----------------- | ------------------ | | Accommodation | 576 Vacation Homes | | Lowest Price | CA $262 | | Highest Price | CA $1,254 | ## Explore a world of travel with Expedia - 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