Title: Chestertown B&B: Find the Best Bed and Breakfast | 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 a Bed and Breakfast in Chestertown ![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 prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&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&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown B&B ![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/2000000/1540000/1539000/1538972/4c20fc37.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) ### The Fern Lodge Chestertown 9.8/10 Exceptional (47) "Comfortable, friendly, beautiful lodge, spacious facilities" [](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=2025-10-23&endDate=2025-10-24®ionId=89045&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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-Bed-And-Breakfast.d89045-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Bed-And-Breakfast.d89045-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Lakefront Terrace Resort](//images.trvl-media.com/lodging/1000000/900000/899000/898952/7471e44f_y.jpg) ### Lakefront Terrace Resort 10/10 Excellent "Clean room with amazing views! Such a unique style building with outdoor hallways" [](https://expedia.ca/Lake-George-Hotels-Lakefront-Terrace-Resort.h898952.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) ![La Quinta Inn & Suites by Wyndham Lake George](//images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/4b0bd02a_y.jpg) ### La Quinta Inn & Suites by Wyndham Lake George 10/10 Excellent "The only thing you should do is have better lighting for your entrance from the road. It’s easy to drive past the entrance and not see it. " [](https://expedia.ca/Lake-George-Hotels-The-George-NY.h82499882.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) ![Clarion Inn & Suites at the Outlets of Lake George](//images.trvl-media.com/lodging/1000000/30000/26400/26327/b39bcc22_y.jpg) ### Clarion Inn & Suites at the Outlets of Lake George 10/10 Excellent "Room was clean " [](https://expedia.ca/Lake-George-Hotels-Clarion-Inn-Suites-At-The-Outlets-Of-Lake-George.h26327.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) ![Admiral Motel](//images.trvl-media.com/lodging/19000000/18530000/18528500/18528423/a3b9e25a_y.jpg) ### Admiral Motel 10/10 Excellent "The service from the front desk was outstanding. For a budget place this motel exceeded expectations" [](https://expedia.ca/Lake-George-Hotels-Admiral-Motel.h18528423.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) ## Find out more about Chestertown ## Chestertown B&B information | Number of reviews | 42 | | --- | --- | | Accommodation | 4 B&B | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### Searching for B&Bs in Chestertown? > If you're looking for something a little different than your standard hotel experience, a bed and breakfast could be a great option for your trip. If you're hoping to spend some time walking along the water in Chestertown, Loon Lake Beach is worth a visit. ### How do you know if a B&B is the best choice for your stay? > With attentive service, opportunities to meet other guests, and tasty breakfasts, B&Bs all have a one-of-a-kind setting. ### What are the top B&Bs in Chestertown? > Here are some B&Bs in the surrounding area: [The Fern Lodge](https://www.expedia.ca/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information): 5 rooms. 3.1 mi (4.9 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and hot tubs. [The Loft at The Remington](https://www.expedia.ca/Lake-George-Hotels-The-Loft-At-The-Remington.h24946427.Hotel-Information): 0.1 mi (0.1 km) from the downtown core. [4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel](https://www.expedia.ca/North-Creek-Hotels-4-Bedroom-Bed-Breakfast-In-Distinct-North-Creek.h110225066.Hotel-Information): Located 9.8 mi (15.8 km) from the core of Chestertown. ### When is the best time to stay at a B&B in Chestertown? > When you're dreaming of a stay in Chestertown, year-round temperatures and rainfall may be important factors to consider. 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? > When you want to spend some time in the great outdoors, Loon Lake Beach and Friends Lake are some notable spots. You might put Loon Lake and Hudson River on your list if you want to see more of the area. ### How can I get to and around Chestertown? > Mapping out your trip in and around Chestertown is easy with these transportation options. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the heart of the city. 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