Find hotels in Chestertown, NY from $46

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, offering activities like skiing, hiking, and exploring beautiful lakes and beaches.
• Charming Atmosphere: The town features a picturesque city center with inviting parks, perfect for leisurely strolls and relaxation.
• Family-Friendly Fun: Enjoy a variety of activities, including indoor waterparks and recreation options suitable for all ages.
• Romantic Getaways: Couples will find serene escapes and romantic spots, ideal for an intimate vacation.
• Diverse Accommodations: Chestertown offers a range of lodging options, from cozy lodges to unique agritourism properties.

Find great hotels near Chestertown

Explore the charming town of Chestertown, New York, where a variety of accommodations await to enhance your vacation experience. From cozy lodges to unique agritourism properties, you'll find options for every traveler. Whether you're seeking adventure, a family-friendly getaway, or a pet-friendly retreat, Chestertown has the perfect hotel for you. Discover top-rated hotels and read reviews to ensure a memorable stay in this picturesque destination.

• Super 8 by Wyndham Lake George/Warrensburg Area: Ideal for the practical traveler, Super 8 by Wyndham Lake George/Warrensburg Area offers a convenient and comfortable motel experience just 12 miles from Chestertown. This pet-friendly establishment caters to both leisure and business travelers, providing essential amenities such as free Wi-Fi and business services. With a welcoming atmosphere for pets—allowing dogs only—and a waived fee for service animals, it ensures that your furry friends can join you on your trip. Enjoy a straightforward stay with easy access to local attractions and the comfort of home.
• The Alpine Lodge: For a romantic getaway immersed in nature, The Alpine Lodge is your perfect sanctuary, located 10 miles from Chestertown. This charming 3-star lodge offers a delicate blend of city charm and natural beauty. With its romance packages and special amenities like Champagne service, it's designed for couples looking to create lasting memories. Nestled in the city center, The Alpine Lodge provides easy access to local dining and attractions, making it an ideal choice for those seeking both adventure and intimacy.
• North Creek Lodge at Gore Mountain: Adventure enthusiasts will find their haven at North Creek Lodge at Gore Mountain, situated 10 miles from Chestertown. With a 3.5-star rating, this lodge caters to thrill-seekers with a variety of outdoor activities, including skiing, hiking, and mountain climbing, all available nearby. The lodge's focus on adventure sports ensures an exhilarating stay, while its cozy accommodations provide a perfect retreat after a day full of excitement. Experience the great outdoors while enjoying the comforts of a well-appointed lodge.

Where to stay in and around Chestertown

Chestertown offers a perfect blend of outdoor adventures and serene escapes, making it an ideal weekend getaway. Explore the charming city center and enjoy walking distance access to clean parks and scenic spots. Nearby areas provide trendy dining options and family-friendly activities, ensuring a delightful experience for all travelers. Whether you seek romance or recreation, Chestertown and its surroundings promise unforgettable moments immersed in nature and relaxation.

• Brant Lake: Nestled a mere 3 miles from Chestertown, Brant Lake is a charming destination that captivates visitors with its stunning outdoor scenery. Known for its peak travel season between June and August, this city offers a romantic atmosphere perfect for couples and nature lovers alike. Outdoor enthusiasts can indulge in skiing at nearby resorts, while the picturesque lake and surrounding mountains provide a serene backdrop for relaxation. Whether you're looking for an adventurous day on the slopes or a tranquil evening by the beach, Brant Lake promises an unforgettable experience.
• The Glen: As a quaint village in the Chestertown area, The Glen attracts visitors seeking a blend of outdoor adventure and romantic escapades, especially during the summer months. The landscape is adorned with beautiful lakes, parks, and beaches, making it an ideal spot for leisurely strolls and picnics. Skiing is a popular activity here, with ski fields and resorts nearby drawing winter sports enthusiasts. The Glen’s charming ambiance and scenic beauty create a welcoming environment for travelers looking to unwind and enjoy nature.
• Chester Shores: Located in close proximity to Chestertown, Chester Shores is a delightful neighborhood that appeals to outdoor lovers and those in search of a picturesque getaway. With peak visitor arrivals in the summer, the area is known for its breathtaking landscapes that include lakes, beaches, and mountains. Adventure seekers can partake in skiing at local resorts, while couples can savor the romantic settings perfect for a retreat. Chester Shores offers a perfect balance of thrill and tranquility, ensuring a memorable vacation experience.

Things to do near Chestertown

Chestertown, New York, is a perfect destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy thrilling activities like skiing at local resorts and exploring the stunning scenery. For family-friendly fun, don't miss the indoor waterpark and various outdoor recreation options that cater to all ages. With its charming atmosphere, Chestertown promises an unforgettable vacation experience.

Shopping

In Chestertown, you'll find charming shops for unique gifts and souvenirs. If you're up for a drive, the Outlets at Lake George and Adirondack Outlet Mall, both 21 miles away, offer a variety of stores and entertainment options. The Shirt Factory, 25 miles away, features local art and crafts.

Recreation

North Creek Ski Bowl Town Park offers a serene environment with trails for hiking and cross-country skiing, perfect for relaxation and wellness. Shepard's Beach Park features beautiful waterfront views and picnic areas for a tranquil day outdoors. Around the World Miniature Golf combines fun and adventure for family bonding.

Adventure

At Gore Mountain Ski Resort, enjoy thrilling skiing experiences on diverse trails, set in a beautiful winter landscape, located 10 miles from Chestertown. For adrenaline seekers, the Adirondack Extreme Adventure Course offers an exhilarating zipline and ropes course adventure, also 10 miles away, surrounded by stunning outdoor scenery.

Nightlife

Experience the charm of Seagle Music Colony, a theater offering captivating performances just 12 miles from Chestertown. For a movie night, visit the Strand Theater, 13 miles away, showcasing the latest films. For some fun-filled adventure, check out the Adventure Racing Family Fun Center, located 22 miles out.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, plan your visit during the cheaper months of January, March, or November, and consider staying on a Tuesday for the best rates. Avoid peak season from July to September. Use Expedia to compare room rates and filter by budget, and consider booking a package with flights and activities for additional savings. Joining Expedia's One Key membership can provide exclusive discounts and earn OneKeyCash for future stays. Explore free activities in the area to stretch your budget further.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are January, March 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 refine your preferences, such as your budget, desired location, and the type of hotel you’re looking for. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel booking in Chestertown with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Chestertown

Chestertown, New York, is perfect for outdoor enthusiasts and those seeking a romantic getaway. With its beautiful lakes, scenic beaches, and inviting island resorts, there's plenty to explore. Visitors can enjoy a range of outdoor activities that showcase the area's natural beauty, making it an ideal destination for relaxation and adventure. Whether you're looking to unwind or embark on new experiences, Chestertown has something for everyone.

• The Sagamore Golf Club: Located 8 miles from Chestertown, this exclusive island resort offers a stunning golf experience with picturesque views and meticulously maintained fairways. It’s perfect for both seasoned golfers and those looking to enjoy the serene environment.
• Friends Lake: Situated right in Chestertown, Friends Lake is a beautiful spot for relaxation and romance. With its sandy beach and scenic backdrop, it's ideal for outdoor activities like swimming, picnicking, and enjoying the tranquil surroundings.
• Natural Stone Bridge and Caves: Just 7 miles away, this adventure destination features unique geological formations and trails for exploration. Experience the thrill of discovering caves and stunning stone bridges in a breathtaking outdoor setting.

Best time to go to Chestertown

The best time to visit Chestertown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chestertown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chestertown falls in January, 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	Slightly Low
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	Average
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

Traveling to Chestertown, New York, can be convenient with several nearby airports. Rutland Southern Vermont Regional Airport (RUT) is 44 miles away, with good hotel options like Killington Mountain Lodge and Killington Grand Hotel, both around 10-11 miles from the airport. Adirondack Regional Airport (SLK) is located 54 miles from Chestertown, offering accommodations such as the 4-star Hotel Saranac. Closer, Floyd Bennett Memorial Airport (GFL) is just 24 miles away, featuring hotels like Six Flags Great Escape Lodge and Top of the World Resort within 5-9 miles. Each airport provides accessible transportation options to ensure a smooth journey to your destination.