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Find hotels in Chestertown, NY from $51

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Compare 1,473 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

More cheap stays in Chestertown

Stay near popular Chestertown attractions

Chestertown Travel Info

Number of reviews
6,020
Accommodation
1,473 hotels
Highest price
$566
Lowest price
$51
Reasons to visit
Loon Lake Beach, Natural Stone Bridge and Caves and Friends Lake
Hotels with horseback riding
25
Hotels with family-friendly amenities
3

Frequently asked questions

Where is the best place to stay in Chestertown?

Friends Lake Inn is one of the top choices for your stay based on our traveler data. This hotel offers a restaurant and free parking. Two other choices for your visit to the area are Six Flags Lodge & Indoor Waterpark and La Quinta Inn & Suites by Wyndham Lake George. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best vacation rentals that Chestertown has to offer?

Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK: This vacation home rental outside of Chestertown is located on a lake and has a fireplace, a balcony, and air-conditioning 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Chestertown.

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

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.

Where can I learn more about changing or cancelling my trip to Chestertown?

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

What's the best accommodation for a budget-friendly stay in Chestertown?

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.

What's the best accommodation for a family vacation 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.

What's the best hotel for couples 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.

What's the best pet-friendly accommodation in Chestertown?

Pine Tree Motel & Cabins is a top property for people traveling with their pets, and offers free WiFi for its human guests. See more pet-friendly hotel accommodations in Chestertown.

What's the best place to stay close to Loon Lake Beach?

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.

What's the best hotel for a beach vacation in Chestertown?

Pine Tree Motel & Cabins is a top beach property offering free WiFi and free parking, located within a short 11-minute walk of Loon Lake Beach. See more stays near the beach in Chestertown.

What's the best luxury place to stay 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.

What's the best place to stay for a winter vacation 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.

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