Hotels in Chestertown
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Top Rated Chestertown Hotels

Six Flags Great Escape Lodge & Indoor Waterpark

La Quinta Inn & Suites by Wyndham Lake George

The Queensbury Hotel

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Courtyard by Marriott Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Express Queensbury - Lake George Area by IHG

Best Western of Lake George

Fort William Henry Hotel and Conference Center

Super 8 by Wyndham Lake George/Warrensburg Area

Walk to Million Dollar Beach from this awesome Cottage!

Baymont by Wyndham Queensbury / Lake George
How much is a Chestertown hotel?
Check Chestertown hotel room prices by star rating

4 Star Hotels
Top reasons to visit Chestertown
- Outdoor Adventure: Chestertown is a haven for outdoor enthusiasts, with its lakes, forests, and secluded areas perfect for canoeing, horseback riding, and boating.
- Charming Cafes: Coffee lovers will find themselves in heaven with the quaint cafes in Chestertown serving up delicious brews to satisfy any caffeine craving.
- Serene Views: Nestled near picturesque lakes, Chestertown offers breathtaking views that are perfect for relaxation and taking in the tranquility of nature.
- Marina Excursions: Embark on boating adventures from the marina in Chestertown, allowing you to explore the surrounding waters and soak up the sun.
- Tasty Seafood: Indulge in the mouthwatering fresh seafood options available in Chestertown, satisfying your cravings for delectable flavors of the sea.
Popular hotels in Chestertown
Chestertown, a charming town in upstate New York, offers a variety of hotel accommodations for every type of traveler. From cozy bed and breakfasts tucked away in the picturesque countryside to modern hotels in the heart of town, there is something for everyone. Whether you're looking for a luxurious stay with all the amenities or a budget-friendly option that still delivers comfort, Chestertown has it all. So, pack your bags and get ready to explore the best of what Chestertown has to offer!
- Six Flags Lodge & Indoor Waterpark - This 3.5-star resort is located 21.4 miles away from Chestertown. It offers close proximity to a waterpark, lazy river, and theme park, making it a great option for outdoor water activities. With amenities like waterslides, an arcade, and an indoor pool, there are plenty of entertainment options for the whole family.
- The Queensbury Hotel - Situated 24.8 miles away from Chestertown, this 3.0-star hotel is known for its friendly staff and close proximity to waterfalls. It also offers access to snow tubing, making it a good choice for outdoor winter activities. The hotel features an indoor pool, perfect for relaxation after a day of exploring.
- Courtyard by Marriott Lake George - This 3.0-star hotel is located 16.2 miles away from Chestertown and offers a picturesque view of the nearby lake. With its friendly atmosphere and proximity to cafes and small town charm, it provides a great option for outdoor enthusiasts looking for a relaxing getaway. The hotel also features an indoor pool and a bar for added convenience.
Top things to see and do in Chestertown
When visiting Chestertown, New York, you'll find yourself surrounded by a variety of enjoyable activities. The charming town is nestled near picturesque lakes, offering opportunities for relaxing and taking in the serene views. If you're a coffee lover, there are quaint cafes that serve up delicious brews. Nature enthusiasts will appreciate the nearby forests, perfect for hiking and exploring. The secluded atmosphere also makes it an ideal spot for canoeing and horseback riding. For those who prefer the water, there's a marina where you can embark on boating adventures. And don't forget to indulge in the fresh seafood options available in Chestertown. With its family-friendly activities and proximity to Lake George and Schroon Lake, Chestertown is a must-visit destination.
- Loon Lake Beach: Enjoy a serene beach experience at Loon Lake Beach. With its close proximity to the beach, you can bask in the sun, build sandcastles, and take refreshing swims. The crystal-clear water and sandy shores create a picturesque setting for relaxation and fun.
- Friends Lake: Immerse yourself in the romantic and scenic beauty of Friends Lake. Surrounded by coffee shops, forests, and secluded spots, this lake offers the perfect backdrop for a peaceful getaway. Take a leisurely canoe ride, go horseback riding, or simply unwind by the marina. The tranquil atmosphere and stunning views make it an ideal destination for outdoor enthusiasts and nature lovers.
- Loon Lake: Experience the breathtaking beauty of Loon Lake. This lake offers a serene and relaxing atmosphere, with its proximity to coffee shops, forests, and secluded areas. Whether you choose to go canoeing, enjoy a boat ride, or indulge in some fresh seafood, Loon Lake promises a memorable outdoor and scenic experience. Immerse yourself in the tranquility and natural charm of this hidden gem.
Best places to visit in Chestertown
Chestertown, New York offers a perfect outdoor vacation with its close proximity to lakes, forests, and secluded areas. Experience the thrill of canoeing, horseback riding, and boating in the beautiful Adirondacks. Don't miss the delicious seafood and the relaxing vibes of this charming town beach.
- Chester Shores: Chester Shores is not your average neighborhood. Nestled near Chestertown, it offers a unique outdoor experience that will leave you in awe. Picture yourself surrounded by picturesque shores, where you can indulge in various water activities like kayaking, paddleboarding, and fishing. The calm and serene atmosphere makes it a perfect spot for a peaceful getaway. If you're a nature enthusiast, you'll be delighted by the abundance of wildlife and beautiful hiking trails. Whether you're looking to relax or seek adventure, Chester Shores has it all. Don't miss out on this hidden gem that promises an unforgettable outdoor holiday.
Seasonal travel trends of Chestertown
The popularity of Chestertown shows no change throughout the year. The most popular time to visit is between June and August, with a seasonal peak in July. The off-peak tourist season is from October and December, with November typically being the quietest month.
Check out the month-by-month weather chart for Chestertown to help you plan your next trip. With a monthly average of 69.1 degrees Fahrenheit, you can expect the hottest temperatures in July. The coldest month, on average, is January. The most rainfall typically happens in June. Regardless of when you visit Chestertown, every season has a reason to stay.
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January | 20.3°F (-6.5°C) | Light Rain | Mostly Cloudy |
February | 22.3°F (-5.4°C) | Light Rain | Mostly Cloudy |
March | 30.4°F (-0.9°C) | Light Rain | Mostly Cloudy |
April | 42.6°F (5.9°C) | Light Rain | Mostly Cloudy |
May | 55.9°F (13.3°C) | Light Rain | Mostly Sunny |
June | 63.1°F (17.3°C) | Light Rain | Mostly Sunny |
July | 69.1°F (20.6°C) | Light Rain | Mostly Sunny |
August | 67.1°F (19.5°C) | Light Rain | Mostly Sunny |
September | 60.3°F (15.7°C) | Light Rain | Mostly Sunny |
October | 48.6°F (9.2°C) | Light Rain | Mostly Cloudy |
November | 36.1°F (2.3°C) | Light Rain | Mostly Sunny |
December | 27.5°F (-2.5°C) | Light Rain | Mostly Cloudy |
Local eateries in Chestertown
In Chestertown, New York, you'll discover a delightful food and dining culture that caters to diverse tastes. Friends Lake Inn, a highly rated and popular restaurant, offers a North American menu that tantalizes your taste buds. Indulge in their delectable dishes that range from succulent steaks to freshly caught seafood. For craft beer enthusiasts, Chestertown is home to several breweries that serve up unique and flavorful brews. If you're in the mood for a quick bite, head to Crossroads Deli for their mouthwatering sandwiches. And for a morning pick-me-up, Dunkin Donuts is a go-to spot for their famous coffee and delicious pastries.
Where is a good place to stay in Chestertown?
What are some favorite hotels to stay with pets in Chestertown?
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is a pet-friendly lodge with free WiFi, private decks, and a game room.
What are the best hotels in Chestertown?
Consider these top hotels around Chestertown:
- Holiday Inn Resort Lake George - Adirondack Area by IHG is located 17 mi away, and this hotel has free WiFi, free parking, and a fitness center.
- Six Flags Great Escape Lodge & Indoor Waterpark is located 21.4 mi away, and this resort has a free water park, 3 restaurants, and 2 bars.
- The Queensbury Hotel is located 24.9 mi away, and this hotel has 2 restaurants, 2 bars, and free WiFi.
Enjoy the natural setting of Chestertown and experience the lakefront.
What are the best hotels to stay near Friends Lake?
If you want to stay within a short distance of Friends Lake, we can help you out. About 1 mile from the center of Chestertown, this body of water is near some convenient hotels. You'll be able to roll out of bed and go straight there from Beautiful Lakeview Cottage on Friends Lake (0.1 miles away). You could also investigate what's on offer at A Beautiful Lake View Cabin on Friends Lake (0.1 miles away) and The Fern Lodge (0.2 miles away).
Chestertown hotels essential information
Accommodation | 1,461 hotels |
---|---|
Lowest Price | $72 |
Highest Price | $223 |
Popular hotels | Six Flags Great Escape Lodge & Indoor Waterpark, La Quinta Inn & Suites by Wyndham Lake George, The Queensbury Hotel, Country Inn & Suites by Radisson, Lake George (Queensbury), NY, Courtyard by Marriott Lake George, Holiday Inn Resort Lake George - Adirondack Area by IHG, Holiday Inn Express Queensbury - Lake George Area by IHG, Best Western of Lake George, Fort William Henry Hotel and Conference Center, Super 8 by Wyndham Lake George/Warrensburg Area, Walk to Million Dollar Beach from this awesome Cottage!, Baymont by Wyndham Queensbury / Lake George |
Booking tips for Chestertown
Booking tips for Chestertown
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Saving tips for your trip
If you're looking to save money on your trip to Chestertown, consider visiting during the less popular season from October to December. During this time, you can take advantage of discounted prices on flights, hotels, and car rentals by bundling them together. When you're in Chestertown, take advantage of the affordable local attractions such as exploring the nearby forests, going horseback riding, or enjoying some delicious seafood. These activities will allow you to experience the beauty of the area without breaking the bank.
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