Find hotels in Chestertown, NY from $61

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown is a paradise for outdoor enthusiasts, offering skiing, hiking, and water activities amidst stunning natural scenery.
• Charming Downtown: Stroll through the quaint downtown area, featuring unique shops, local eateries, and picturesque views.
• Scenic Lakes and Beaches: Enjoy beautiful lakes and relaxing beaches perfect for sunbathing and picnicking.
• Family-Friendly Activities: The Emmorton Recreation area provides fun and engaging experiences for the whole family.
• Diverse Accommodations: Choose from cozy lodges to unique agritourism properties for a comfortable stay.

Find great hotels near Chestertown

Chestertown offers a variety of hotel accommodations to cater to every traveler's needs, from cozy lodges to unique agritourism properties. Whether you're seeking adventure, a family-friendly getaway, or a pet-friendly experience, you'll find plenty of options. Explore the best hotels in Chestertown, where comfort and convenience meet the charm of this beautiful area.

• Super 8 by Wyndham Lake George/Warrensburg Area: A budget-friendly motel with a solid guest rating of 8.8, Super 8 by Wyndham Lake George/Warrensburg Area is located 12 miles from Chestertown. Ideal for travelers seeking a pet-friendly environment, this hotel welcomes furry companions with specific pet policies. The property caters to both leisure and business travelers, offering practical amenities that ensure a comfortable stay. Guests appreciate the clean and cozy rooms, along with the convenience of being close to local attractions.
• The Alpine Lodge: A charming 3-star lodge boasting a guest rating of 9.0, The Alpine Lodge is situated 10 miles from Chestertown and is perfect for those seeking adventure and romance. With easy access to ski shuttles and lifts, this lodge is a winter wonderland for skiers and snowboarders. It features an array of exciting outdoor activities, such as mountain climbing, kayaking, and horseback riding. For couples, the lodge offers special romance packages, including champagne service, making it an ideal setting for a memorable getaway.
• North Creek Lodge at Gore Mountain: Rated 3.5 stars and located 10 miles from Chestertown, North Creek Lodge at Gore Mountain is tailored for adventure enthusiasts. This lodge provides various recreational activities nearby, including hiking, snowboarding, and cave exploring. Guests can immerse themselves in nature while enjoying the comfort of well-appointed accommodations. With its focus on outdoor experiences, this lodge is a great choice for travelers looking to explore the stunning landscapes and partake in thrilling adventures.

Where to stay in and around Chestertown

Chestertown, New York, offers a delightful blend of outdoor adventures and scenic beauty, perfect for those seeking a relaxing getaway. Explore the charming downtown area, take in picturesque views of the Chesapeake Bay, or enjoy the Emmorton Recreation area for family-friendly activities. Nearby, you'll find trendy neighborhoods that cater to luxury and adventure, ensuring a memorable vacation filled with various vibes—from secluded retreats to vibrant recreational experiences.

• Bolton Landing: Located 10 miles from Chestertown, Bolton Landing is a charming destination celebrated for its stunning outdoor scenery and romantic ambiance. With a peak tourist season from June to August, visitors flock here for golfing at its private country clubs and the picturesque views of the nearby lake and island resort. The area is perfect for those looking to unwind and enjoy the natural beauty, making it a favorite summer getaway for families and couples alike.
• Brant Lake: Just 3 miles away from Chestertown, Brant Lake is a hidden gem that thrives during the summer months, attracting outdoor enthusiasts and nature lovers. Known for its ski resorts and breathtaking mountain views, this destination is particularly popular from June to August. Visitors can indulge in skiing during the winter or relax by the lake and beach in warmer months. Brant Lake offers a serene escape, perfect for those seeking adventure and relaxation in a beautiful setting.
• Chester Shores: Nestled around Chestertown, Chester Shores is a delightful neighborhood that draws travelers seeking scenic views and outdoor activities. With peak visitation from July to September, this area is renowned for its skiing opportunities and access to urban parks. The nearby lake and mountains create a picturesque backdrop, making it an ideal spot for romantic getaways or family outings. Chester Shores is where you can truly immerse yourself in nature while enjoying a variety of recreational activities.

Things to do in Chestertown

Chestertown, New York, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Visitors can enjoy skiing at local resorts, explore the scenic beauty of the area, and partake in various outdoor recreational activities. With a range of entertainment options, local attractions, and wellness retreats, Chestertown offers a delightful blend of adventure and relaxation for everyone looking to unwind in nature.

Shopping

In Chestertown, enjoy local shops like the Chestertown Farmer's Market for unique gifts and handmade souvenirs. If you're up for a drive, visit the Lake George Plaza, about 12 miles away, featuring various stores and dining options for a more extensive shopping experience.

Recreation

In Chestertown, the Adirondack Wellness Center provides holistic therapies, yoga classes, and serene nature walks, promoting relaxation and rejuvenation. Enjoy the nearby Loon Lake, perfect for kayaking and fishing, offering a peaceful escape into nature while enhancing your well-being.

Adventure

Chestertown offers thrilling adventures at the nearby Adirondack Mountains, where you can hike scenic trails, kayak on serene lakes, and enjoy breathtaking views. Explore the Hudson River for fishing and whitewater rafting, or visit the local parks for biking and nature walks amidst beautiful landscapes.

Nightlife

Chestertown offers a cozy nightlife with local charm. Enjoy a drink at the friendly Loon Lake Lodge or experience live music at the charming Chestertown Community Theatre. For a relaxed evening, grab a bite at a local diner and soak in the small-town atmosphere.

Booking tips and Expedia advantages for Chestertown

• 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: Expedia's search tool makes it easy for you to choose your budget, preferred location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you find the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
• 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, New York, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering stunning scenery and a variety of attractions. Visitors can explore beautiful lakes, relaxing beaches, and charming island resorts. Whether you're looking for adventure or a peaceful retreat, Chestertown's local points of interest provide an ideal setting for memorable experiences amidst nature.

• Friends Lake: Nestled in Chestertown, Friends Lake offers a serene escape with its beautiful outdoor scenery. Enjoy romantic strolls along the shore, picnics on the beach, and various water activities, making it perfect for relaxation and adventure alike.
• Loon Lake Beach: This picturesque beach is a local favorite, providing a tranquil environment for sunbathing, swimming, and enjoying the scenic views. It's an ideal spot for families and friends to unwind and soak in the sun.
• The Sagamore Golf Club: Located 8 miles from Chestertown, this exclusive island resort boasts a stunning golf course with panoramic views. Experience world-class golfing amidst lush landscapes and unwind at the luxurious amenities available on-site.

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	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

When visiting Chestertown, New York, you have several airport options within a reasonable distance. ALBany International Airport (ALB) is 63 miles away, with nearby hotels like The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. Burlington International Airport (BTV) is 65 miles from Chestertown, offering accommodations such as DoubleTree by Hilton Burlington Vermont, just 2 miles away. Lastly, Plattsburgh International Airport (PBG) is 72 miles distant, with options like Days Inn by Wyndham Plattsburgh, located 2 miles from the airport. Each airport provides accessible transportation services to their respective hotels.