Hotels in Chestertown

Whispers of the Lake: Unveiling Chestertown's Enchanted Forests and Marina Wonders

Nestled in the heart of the Adirondacks, Chestertown, New York, is a charming off-the-beaten-path retreat perfect for a romantic getaway or a serene escape into nature. Surrounded by lush forests and pristine lakes, this idyllic destination offers opportunities for kayaking, hiking, and unwinding by the tranquil shores. Explore the quaint local shops, savour delectable cuisine at cozy eateries, and discover the vibrant arts scene. With its stunning landscapes and welcoming atmosphere, Chestertown is a hidden gem that invites you to reconnect with nature and each other. Experience the beauty and charm of upstate New York—your adventure awaits. For great hotel rates in Chestertown, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Chestertown

Chestertown offers a range of friendly accommodations, from charming inns and cozy bed and breakfasts to affordable hotels. Whether you're seeking a budget-friendly stay or a more comfortable retreat, you'll find various options that cater to different tastes and needs in this scenic area of New York. Here are some of the most popular hotels with our travelers in Chestertown:

1. HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!Opens in a new window: HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles! is a charming 3.0-star castle-style hotel that offers an exceptional adventure vacation experience. With direct access to the beach and proximity to ski shuttles, it caters perfectly to leisure travelers seeking both relaxation and excitement. Guests can indulge in a variety of adventure sports, including mountain climbing, horse riding, tubing, snorkeling, and motorboating, all available onsite or nearby. The unique architectural design and recreational activities create a memorable stay, making it a favourite among those looking for distinctive experiences and comfort.
2. Contessa ResortOpens in a new window: Contessa Resort is a welcoming 2.5-star motel that provides a straightforward beach vacation experience. With direct beach access, it is a fantastic option for leisure travelers who appreciate the simplicity of a relaxed coastal getaway. The property’s inviting atmosphere and convenient location allow guests to unwind and enjoy the sun and surf with ease. Reviewers highlight the warm ambiance and accessibility to beach activities, making it a delightful choice for those seeking a stress-free escape by the water.
3. Gore Mountain LodgeOpens in a new window: Gore Mountain Lodge is a cozy 2.0-star motel that perfectly blends beach and ski vacation experiences. With direct access to the beach and nearby ski shuttles, it caters to leisure travelers who enjoy both water and winter sports. The inviting environment and accessibility to both beach activities and ski facilities create a unique retreat for adventurous spirits. The property is appreciated for its convenient location, offering a seamless blend of relaxation and outdoor excitement, appealing to those looking to explore diverse recreational options.

Top locations to stay in Chestertown

Some of the great areas to stay in when visiting Chestertown, New York, are Bolton Landing, Warrensburg, and North Creek. Bolton Landing offers a charming lakefront experience, ideal for relaxation. Warrensburg is nestled by the river, perfect for outdoor adventures, while North Creek is a winter wonderland, renowned for skiing and hiking. For first-time visitors, Bolton Landing is particularly appealing for its serene atmosphere and beach access.

1. Bolton LandingOpens in a new window: Nestled on the shores of Lake George, Bolton Landing is the perfect getaway for those who love the water. With its stunning lakeside views, you can indulge in activities like boating, swimming, and fishing. The charming downtown area features unique shops and boutiques where you can find local crafts and souvenirs. Plus, the scenic hiking trails nearby offer breathtaking views of the lake and surrounding mountains, making it an ideal spot for outdoor enthusiasts.
2. North CreekOpens in a new window: If you're seeking a blend of adventure and relaxation, North Creek is a fantastic choice. Known for its proximity to ski resorts, it's a winter wonderland for skiing and snowboarding. In the warmer months, the area transforms into a hiker's paradise with trails that cater to all skill levels. The town also boasts a vibrant arts scene, with cultural attractions that showcase local talent, making it a well-rounded destination for all types of travelers.
3. WarrensburgOpens in a new window: Situated along the Hudson River, Warrensburg offers a quaint, small-town experience with a strong connection to nature. It’s a great place for river-related activities like kayaking and fishing, and the surrounding forests provide ample opportunities for hiking and exploring. The local shops and markets reflect the town's history and charm, giving you a taste of the region's culture. Don’t miss the seasonal events that often take place here, adding to the vibrant community spirit.

Things to do in Chestertown

Nestled among tranquil lakes and lush forests, Chestertown invites travellers to explore its stunning natural beauty. Enjoy a day of canoeing across serene waters, or set sail for a leisurely boating experience. With picturesque parks and scenic trails, it’s an ideal spot for outdoor enthusiasts seeking relaxation or adventure.

• Natural Stone Bridge and CavesOpens in a new window – Explore the stunning Natural Stone Bridge and Caves, where you can wander through fascinating caverns and witness the beauty of nature up close. The unique geological formations and the surrounding forest make this a perfect spot for hiking and photography.
• Revolution Rail Co.Opens in a new window – Hop aboard the historic Revolution Rail Co. for an exhilarating ride along scenic trails. Enjoy the fresh air as you pedal through picturesque landscapes, taking in the sights of the charming countryside and nearby lakes.
• Blue Line Outdoor CenterOpens in a new window – Dive into outdoor fun at the Blue Line Outdoor Center. Whether you’re looking to kayak, hike, or simply relax in nature, this facility offers everything you need to enjoy a day surrounded by the beautiful Adirondack Mountains.
• The Sagamore Golf ClubOpens in a new window – Tee off at The Sagamore Golf Club, an exquisite resort that boasts a stunning golf course with breathtaking views of the lake. Perfect for both seasoned golfers and newcomers, this venue promises a memorable day on the green.
• Rogers Memorial Park BeachOpens in a new window – Unwind at Rogers Memorial Park Beach, where you can soak up the sun on sandy shores. Take a swim in the refreshing lake or enjoy a picnic with family and friends as you relish the tranquil atmosphere of this lovely beach.

4 tips for savvy savings when booking a hotel in Chestertown

1. Book for the cheapest times: The most budget-friendly time to visit Chestertown is during January, March, and November, when hotel prices may drop. For a great value for money experience, it's recommended to stay for at least 2 to 3 days to fully appreciate the historical landmarks and cultural attractions. During your visit, you can enjoy the serene lakes, explore the forests, or indulge in relaxing activities such as canoeing and horseback riding. Don't miss out on the local marina, where you can partake in boating adventures and savour delicious seafood, all while enjoying the quaint coffee shops that add to the charming atmosphere of Chestertown.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Chestertown, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted hotel rates as your travel date approaches. Additionally, enabling email alerts or push notifications can keep you informed about flash sales and special promotions, giving you a chance to save. With Smart ShoppingOpens in a new window, the app's comparison tool, you could find opportunities to compare hotel prices and amenities, ensuring you get the best value. This way, you'll be informed of any price drops or room availability, making your last-minute getaway easier to book.
3. Be flexible with dates: Prices may fluctuate based on factors such as the hotel's location, star rating, and the time of year, so being flexible with your travel dates could help you save on your stay in a Chestertown hotel. For those seeking unique accommodations, boutique hotels can provide a more personalised experience and potentially better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher side, we’ll suggest more affordable dates, which may help you find a better deal.
4. Consider your location: Staying near key attractions or city centres may offer convenience, but it often comes with higher costs. For more affordable options, consider hotels in less central areas or neighbourhoods, balancing price with accessibility to the places you plan to visit. You might also look into independent hotels located further out, which are usually more likely to be affordable and can provide a more authentic experience.

Best time to go to Chestertown

Chestertown experiences its lowest average temperature in January, at 20.3°F (-6.5°C), while July is the hottest month, with an average temperature of 69.1°F (20.6°C). June is usually the wettest month. June to August are the peak travel months in Chestertown, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, October to December tend to be quieter times to visit, marked by light rainfall and mostly sunny to mostly cloudy conditions.