Find hotels in Chestertown, NY from ₩102,646

The Fern Lodge is a favorite 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.

Yes! You'll find that most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

For more details about changing or cancelling your trip to Chestertown, head over to our customer service page.

Based on reviews, Pine Tree Motel & Cabins is a popular 2-star property for our travelers looking for an economical choice, and features free WiFi and free parking. View all budget hotels in Chestertown.

Pine Tree Motel & Cabins is a property with free parking and free WiFi, and it's a top choice on Expedia for families. The Fern Lodge is another choice for your family trip. Attractions in the area like Garnet Hill Lodge and Ski Resort and House of Frankenstein Wax Museum are also fun for kids of all ages. Find more child-friendly accommodations in Chestertown.

Friends Lake Inn is a favorite 4-star hotel for couples, and features a full-service spa and wedding services. Another choice for a romantic stay is The Fern Lodge. See all romantic hotels 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 pet-friendly option for your stay. See more pet-friendly hotel accommodations in Chestertown.

Pine Tree Motel & Cabins is one of the top choices for your stay based on our traveler data, and this property offers free WiFi and free parking. It's located just a short 0.5 mi (0.8 km) from Loon Lake Beach. Another good choice is Friends Lake Inn, located 1.6 mi (2.6 km) away.

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.

Friends Lake Inn is a 4-star hotel with a full-service spa and a terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Chestertown.

Based on our travel data, The Fern Lodge is a top 3.5-star B&B for a winter vacation, and features ski passes and private spa tubs. Friends Lake Inn is another good choice for your ski trip. Those looking to ski or snowboard can spend their days at Gore Mountain Ski Resort.

The Queensbury Hotel: Provides 2 restaurants, an indoor pool, and 2 bars. Best Western of Lake George and Lakefront Terrace Resort are two additional hotels that feature an onsite pool. View all hotels with pools in Chestertown.

Friends Lake Inn is a top spa hotel featuring a bar and a restaurant. See all spa hotels in Chestertown.

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

Visitors to Chestertown are sure to enjoy the lakeside setting. Tourists can also enjoy the city's coffeehouses, forests, and seafood restaurants. In Chestertown, there are 121 hotels and other accommodations 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 agenda are Hudson River and Tripp Pond. Check out what more to see and do in Expedia's Chestertown guide.

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.