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The Fern Lodge is a favourite property for Expedia customers. This B&B offers free breakfast and free parking. Other top choices based on reviews include Pine Tree Motel & Cabins and Friends Lake Inn. See all available top hotels, or vacation rentals in Chestertown.

Eagles Nest at Loon Lake near Gore Mountain: This highly rated holiday home rental in Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a pool table. See all vacation rentals in Chestertown.

Yes, you'll find most room reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

Pine Tree Motel & Cabins is one of the top choices for those in the LGBT community. See all available hotels listed as LGBTQ-friendly in Chestertown.

Pine Tree Motel & Cabins is a top dog-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another option if you're bringing your pet along. See more pet-friendly hotel accommodations in Chestertown.

The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach . See more stays near the beach in Chestertown.

The Queensbury Hotel: Provides 2 restaurants, an indoor pool and 2 bars. Lakefront Terrace Resort and The Georgian Lakeside Resort are two additional hotels that offer an on-site pool. View all hotels with pools in Chestertown.

1970s acreage surrounded by trees with deck, grill, & internet is a favourite water park hotel in Chestertown

Visitors to Chestertown will definitely enjoy the lakeside setting. Tourists can also enjoy the city's coffee shops, forests and seafood restaurants. In Chestertown, there are 120 hotels and other accommodation options to choose from. Find out more about Chestertown.

Natural beauty is on display at Loon Lake Beach, Friends Lake and Loon Lake. A couple of additional sights to add to your itinerary are Hudson River and Tripp Pond. Take a look at what more there is to see and do in Expedia's Chestertown guide.

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.