Find hotels in Chestertown, NY from NT$2,254

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, featuring skiing resorts and beautiful lakes for various recreational activities.
• Scenic Landscapes: The area boasts picturesque views and charming island resorts, perfect for nature lovers and romantic getaways.
• Indoor Waterpark: Families can enjoy thrilling experiences at the local indoor waterpark, offering fun for all ages.
• Charming City Center: Explore the quaint city center filled with clean, welcoming spaces and trendy attractions.
• Diverse Accommodations: Chestertown offers a variety of lodging options, from cozy lodges to unique agritourism experiences.

Find great hotels near Chestertown

Discover a range of inviting accommodations in Chestertown, New York, perfect for family getaways, pet-friendly stays, and adventure-filled vacations. Whether you're seeking a cozy lodge or a unique agritourism experience, Chestertown offers top hotels and lodgings that cater to diverse traveler needs. Explore hotel reviews to find the best options for a memorable stay in this charming destination.

• Super 8 by Wyndham Lake George/Warrensburg Area: A practical choice for both business and leisure travelers, Super 8 by Wyndham offers a convenient stay just 19.3km from Chestertown. This pet-friendly motel is perfect for those who wish to bring their furry companions along on their adventure. With essential amenities including free Wi-Fi, complimentary breakfast, and a welcoming atmosphere, it caters to guests looking for comfort and accessibility. The property also accommodates service animals without any fees, making it an inclusive option for all travelers.
• The Alpine Lodge: Located a mere 16.1km from Chestertown, The Alpine Lodge is an adventure lover’s paradise. This 3-star lodge immerses guests in a nature-themed experience with easy access to skiing, mountain biking, and kayaking activities. The lodge’s rustic charm complements its thrilling offerings, including nearby hunting and horseback riding. After a day of adventure, unwind in cozy accommodations that reflect the beauty of the surrounding landscape. Whether you’re hitting the slopes or exploring the great outdoors, The Alpine Lodge provides the perfect base for your explorations.
• North Creek Lodge at Gore Mountain: Just 16.1km from Chestertown, North Creek Lodge at Gore Mountain is a 3.5-star sanctuary for thrill-seekers and nature enthusiasts. The lodge offers a host of adventure sports, including snowboarding, hiking, and cave exploring, ensuring guests have plenty of options to satisfy their adventurous spirit. With a focus on outdoor recreation, this lodge is ideal for those looking to immerse themselves in the beauty of Gore Mountain. Enjoy a cozy retreat after a day of excitement, making it the perfect getaway for adventure enthusiasts.

Where to stay in and around Chestertown

Chestertown, New York, offers a perfect blend of outdoor adventures and serene scenery, making it an ideal spot for a romantic getaway or a family-friendly vacation. Explore the charming city center, where you can find clean and welcoming spaces, all within walking distance. Nearby attractions provide a trendy atmosphere, perfect for recreation and luxury experiences. Whether you're seeking relaxation or adventure, Chestertown and its surroundings promise a memorable escape.

• Brant Lake: Nestled a mere 4.8km from Chestertown, Brant Lake is a charming destination that offers a delightful mix of outdoor adventures and stunning scenery. This city is particularly popular during the summer months, from June to August, when visitors flock to enjoy the beautiful lake, majestic mountains, and sandy beaches. Whether you're into skiing at local resorts during the winter or relaxing by the water in warmer months, Brant Lake promises a romantic getaway filled with breathtaking moments. Don’t miss the chance to explore its picturesque landscapes and partake in various outdoor activities.
• The Glen: Located within the Chestertown area, The Glen is a quaint village that invites travelers to immerse themselves in its natural beauty. Similar to its neighbors, The Glen sees a spike in visitors from June to August, eager to experience its serene lakes, winding rivers, and lush mountains. Outdoor enthusiasts will love the skiing options available in the winter months, while the village's tranquil atmosphere makes it perfect for a romantic retreat. Be sure to take advantage of the scenic views and enjoy the vibrant community spirit during your stay.
• Chester Shores: Chester Shores is a picturesque neighborhood surrounding Chestertown, characterized by its stunning landscapes and outdoor activities. Like the other areas, it experiences seasonal visitor peaks in the summer, drawing those looking for a romantic escape in nature. The neighborhood is perfect for skiing adventures in winter and offers access to serene lakes, majestic mountains, and beautiful beaches. Whether you’re looking to explore or simply unwind, Chester Shores provides a peaceful environment for making unforgettable memories.

Things to do near Chestertown

Chestertown, New York, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy a variety of activities such as skiing at local resorts, exploring scenic landscapes, and indulging in outdoor recreation. For those looking for indoor fun, an indoor waterpark offers exciting options for all ages. Whether you're hitting the slopes or relaxing by the water, Chestertown has something for everyone to enjoy.

Shopping

In Chestertown, you can enjoy shopping at local boutiques and stores. If you're up for a drive, visit the Outlets at Lake George and Adirondack Outlet Mall, both 33.8km away, offering a variety of shops and entertainment options.

Recreation

At North Creek Ski Bowl Town Park, unwind amidst serene nature trails and enjoy outdoor yoga sessions, just 16.1km from Chestertown. Shepard's Beach Park offers tranquil lakeside walks and picnics, located 25.7km away. For family fun, Around the World Miniature Golf, 27.4km away, combines adventure with relaxation.

Adventure

At Gore Mountain Ski Resort, 16.1km from Chestertown, enjoy thrilling skiing experiences on well-groomed slopes. For an adrenaline rush, visit the Adirondack Extreme Adventure Course, also 16.1km away, where you can zipline and navigate exciting rope challenges amidst the beautiful outdoors. Sagamore Glades, another skiField, offers exhilarating skiing, 16.1km from town.

Nightlife

Experience the vibrant nightlife in Chestertown by visiting Seagle Music Colony for captivating performances, or catch a family-friendly film at the Strand Theater. For some adventure, head to Fun Spot, where you can enjoy arcade games and activities suitable for all ages.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the cheaper months of March to April or November, and aim for a Tuesday stay, which is the least expensive day. Use Expedia to compare room rates, explore exclusive discounts, and find budget options by sorting prices from lowest to highest. Look for package deals that combine your hotel, flights, and activities for additional savings. For free activities, enjoy the natural beauty of the area through hiking and outdoor exploration, which can be both rewarding and cost-effective.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are March to April and November, where the prices are slightly lower. This is in comparison to July to September, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, preferred location, and desired hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Chestertown with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chestertown

Chestertown offers a perfect getaway for outdoor enthusiasts and couples seeking a romantic retreat. Visitors can explore scenic lakes, beautiful beaches, and charming island resorts. This quaint town is an ideal destination for those looking to enjoy nature and relax by the water, making it a great spot for a memorable vacation filled with picturesque experiences.

• The Sagamore Golf Club: Located 12.9km from Chestertown, this stunning island resort offers a premier golfing experience amidst breathtaking views. Enjoy beautifully manicured greens and a serene atmosphere, perfect for both seasoned golfers and beginners looking to improve their swing.
• Friends Lake: Situated within Chestertown, Friends Lake is a picturesque destination known for its romantic scenery and inviting beach. Enjoy a variety of outdoor activities like swimming, kayaking, or simply relaxing by the water, surrounded by nature's beauty.
• Loon Lake Beach: Right in Chestertown, Loon Lake Beach is a charming spot that exudes classic beach vibes. With its sandy shores and tranquil waters, it's an ideal place for sunbathing, swimming, or enjoying a leisurely picnic with family and friends.

Best time to go to Chestertown

The best time to visit Chestertown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	20.3°F (-6.5°C)	Light Rain	Mostly Cloudy	Average	Average
February	22.3°F (-5.4°C)	Light Rain	Mostly Cloudy	Average	Average
March	30.4°F (-0.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	42.6°F (5.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	55.9°F (13.3°C)	Light Rain	Mostly Sunny	Average	Average
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	69.1°F (20.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	48.6°F (9.2°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
November	36.1°F (2.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	27.5°F (-2.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

The nearest major airports for your trip to Chestertown

For a vacation in Chestertown, New York, you can fly into several major airports. Rutland Southern Vermont Regional Airport (RUT), located 70.8km away, offers nearby accommodations like the 3.5-star Killington Mountain Lodge and Snowed Inn, both about 17.7km from the airport. Adirondack Regional Airport (SLK) is 86.9km away, with options like the 4-star Hotel Saranac just 8.0km from the airport. Floyd Bennett Memorial Airport (GFL) is the closest at 38.6km, featuring hotels such as the 4-star Lodges At Cresthaven, 14.5km from GFL. Each airport provides various transportation services to make your journey convenient.