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.

What are some accommodations with pools in Chestertown?

La Quinta Inn & Suites by Wyndham Lake George : Hotel located near Six Flags Great Escape. Offers daily, an indoor pool, and free self parking. The Queensbury Hotel and Country Inn & Suites by Radisson, Lake George (Queensbury), NY are two additional hotels that feature an onsite pool. View all hotels with pools in Chestertown .

What is the best spa hotel in Chestertown?

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

What's the most popular hotel in Chestertown with an on-site water park or a water park nearby?

1970s acreage surrounded by trees with deck, grill, & internet is a favorite water park hotel in ChestertownCheck out all hotels with or near waterparks in Chestertown .

What's the best hotel for staying near Albany International Airport (ALB)?

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 .

What is staying in Chestertown like?

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 110 hotels and other accommodations to choose from. Find out more about Chestertown .

What should I see while I'm in 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 .

What's the weather like in Chestertown?

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.

Photo by Julie Miller

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Stay near popular Chestertown attractions

Loon Lake Beach

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.

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Chestertown Travel Info

Number of reviews	2,563
Accommodation	1,502 hotels
Highest price	$599
Lowest price	$42
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?

Located 21.4 mi (34.5 km) from the heart of Chestertown, Six Flags Lodge & Indoor Waterpark is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham Lake George and The Queensbury Hotel. See all available top hotels, or vacation rentals in Chestertown.

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

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace: This vacation home rental outside Chestertown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books. 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 LGBTQ-friendly place to stay 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.

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

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is a top lodge for people traveling with their pets, and offers an arcade/game room and in-room kitchens for its human guests. Pine Tree Motel & Cabins is another good choice if you're bringing your pet along. 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?

The Fern Lodge is a top beach B&B with free breakfast and 8 spa tubs, and it's located close to 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.