Chestertown Hotels

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.

RUSTIC COUNTRY COTTAGE With SWIMMING POOL: This holiday home rental outside of Chestertown is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and an arcade/games room so that you can immerse yourself in your holiday. 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.

Based on reviews, Pine Tree Motel & Cabins is a popular 2-star property for our travellers 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 good option for your child-friendly holiday. Also, attractions in the area such as Garnet Hill Lodge and Ski Resort and House of Frankenstein Wax Museum are fun for children of all ages. Find more child-friendly accommodations in Chestertown.

Friends Lake Inn is a favourite 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 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.

Friends Lake Inn is a 4-star hotel with a full-service spa and a terrace, and it's a popular choice for Expedia travellers 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 holiday, and features ski passes and private hot tubs. Friends Lake Inn is another good choice for your skiing 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. The Georgian Lakeside Resort and Lakefront Terrace Resort are two additional hotels that offer an on-site 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.

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 122 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.