Find hotels in Chestertown, NY from $83

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, offering skiing, hiking trails, and breathtaking views of Potter Brook.
• Scenic Lakes and Beaches: Enjoy stunning lakes and beautiful beaches perfect for relaxation and recreation.
• Charming Island Resorts: Explore delightful island resorts that provide a unique getaway experience.
• Local Vineyards and Dining: Tour nearby vineyards and savor delicious meals at charming restaurants.
• Cozy Accommodations: Choose from a variety of lodges and hotels, catering to families, couples, and pet owners.

Find great hotels near Chestertown

Discover the charm of Chestertown, New York, where a variety of hotel accommodations await you, ranging from cozy lodges to luxurious stays. Whether you're seeking adventure, a family-friendly getaway, or a pet-friendly retreat, you'll find options that cater to every preference. Explore the top hotels in the Adirondacks and experience the perfect blend of comfort and convenience during your visit to this picturesque destination.

• Super 8 by Wyndham Lake George/Warrensburg Area: This motel is a practical choice for business travelers and pet owners alike, located 12 miles from Chestertown. With a business-themed atmosphere, it offers essential services and facilities tailored to ensure a productive stay. Guests appreciate the pet-friendly policies, allowing dogs and service animals with waived fees. Whether you’re traveling for work or leisure, Super 8 provides a comfortable and convenient base for exploring the Lake George area.
• The Alpine Lodge: Situated 10 miles from Chestertown, The Alpine Lodge invites adventure seekers and couples looking for a romantic getaway. This 3-star lodge is perfect for those eager to hit the slopes, with easy access to ski shuttles and lifts. Onsite, guests can indulge in various adventure sports ranging from horse riding to rafting. The lodge also offers romance packages, complete with champagne service, catering to those looking to create unforgettable memories in a cozy mountain setting.
• North Creek Lodge at Gore Mountain: Located 10 miles from Chestertown, this 3.5-star lodge is ideal for thrill-seekers and outdoor enthusiasts. North Creek Lodge is surrounded by stunning natural landscapes, offering a range of adventure sports like snowboarding, mountain climbing, and hiking. Guests can enjoy the convenience of onsite amenities while exploring the great outdoors. This lodge promises an exhilarating experience for anyone looking to immerse themselves in the beauty of Gore Mountain's recreational opportunities.

Where to stay in and around Chestertown

Chestertown, New York, is a hidden gem perfect for outdoor enthusiasts and couples seeking a romantic getaway. Nestled in the heart of Upstate New York, it offers stunning scenery and a relaxing atmosphere. Nearby destinations provide a blend of trendy and secluded vibes, making it ideal for family vacations or weekend retreats. Explore charming towns and indulge in recreational activities, ensuring a memorable experience in this beautiful region.

• The Glen: Nestled close to Chestertown, The Glen is a charming village that offers a delightful escape for outdoor enthusiasts and romantics alike. This picturesque area sees a surge of visitors from July to September, drawn by its breathtaking scenery and recreational activities. The Glen is particularly popular for skiing, with easy access to local ski resorts and fields. Nature lovers will appreciate the nearby lakes, beaches, and parks, making it an ideal spot for a relaxing getaway or an adventurous outdoor experience.
• Chester Shores: Located in proximity to Chestertown, Chester Shores is a scenic neighborhood that captivates tourists with its stunning landscapes and outdoor activities. Like The Glen, Chester Shores experiences peak visitation from July to September. The area is perfect for those seeking romance or simply wishing to immerse themselves in nature. Visitors can enjoy skiing at nearby resorts and fields, while the surrounding lakes, beaches, and mountains provide ample opportunity for exploration and relaxation. Chester Shores is a hidden gem for those looking to escape the hustle and bustle of everyday life.
• Brant Lake: Just 3 miles from Chestertown, Brant Lake is a vibrant city that draws travelers year-round, with peak visits occurring from June to August. Known for its stunning outdoor scenery, Brant Lake offers a plethora of activities for nature enthusiasts and couples seeking a romantic getaway. Whether you’re skiing at one of the local resorts or enjoying the beauty of the nearby mountains and lakes, Brant Lake is perfect for those who appreciate both adventure and tranquility. With its inviting beaches, this city is a must-visit destination on your vacation itinerary.

Things to do near Chestertown

Chestertown, New York, is a perfect destination for outdoor enthusiasts and romantic getaways. Visitors can enjoy skiing at local resorts, explore scenic hiking trails, and take in breathtaking views of Potter Brook. Don't miss the chance to tour nearby vineyards and savor delightful meals at charming restaurants, making it a well-rounded vacation spot for nature lovers and adventure seekers alike.

Shopping

In Chestertown, you can enjoy charming local shops for unique gifts. If you're up for a drive, the Outlets at Lake George (21 miles away) and the Adirondack Outlet Mall (20 miles away) offer a wider selection. The Shirt Factory is another option, located 25 miles from town.

Recreation

North Creek Ski Bowl Town Park offers a serene atmosphere with trails and natural beauty, perfect for relaxation and wellness. Shepard's Beach Park features scenic views and tranquil settings, ideal for unwinding. For a fun family outing, Around the World Miniature Golf combines adventure and sports in a lively environment.

Adventure

Experience the thrill of skiing at Gore Mountain Ski Resort, located 10 miles from Chestertown, where you can enjoy pristine slopes and vibrant sports energy. For a different adventure, tackle the Adirondack Extreme Adventure Course, also 10 miles away, featuring exciting zip lines and challenging ropes courses amidst beautiful outdoor scenery.

Nightlife

Experience the magic of Seagle Music Colony, just 12 miles away, for a captivating theater performance. Alternatively, catch a romantic film at Strand Theater, 13 miles from Chestertown. For an exciting night, visit Fun Spot, an arcadeAdventureZone located 22 miles away, perfect for family fun and adventure.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the cheaper months of January, March, or November, with Tuesdays being the least expensive days to stay. Utilize Expedia’s search tool to find affordable hotels by sorting prices from lowest to highest, and consider booking a package deal that combines flights and activities. Look for eco-friendly hotel options to save further. Joining Expedia's One Key membership can also provide exclusive discounts and the opportunity to earn OneKeyCash for future stays. Take advantage of free local activities and public transport options to keep costs down.

• 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: Expedia's search tool makes it easy for you to set your budget, choose your desired location, and more. You can arrange your search results to display prices from lowest to highest, helping you find the most affordable hotels right away. Additionally, you can refine your choices by hotel type; for instance, selecting the "Eco-certified" filter will show you sustainable and environmentally friendly hotels that are available for booking.
• Consider bundling your trip: Consider saving money by combining your hotel stay in Chestertown with your flights and activities through an Expedia package deal.
• 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 romantics alike, offering stunning lakes, beautiful beaches, and charming island resorts. Visitors can immerse themselves in the natural scenery while exploring various attractions that cater to outdoor and beach experiences. Don’t miss the nearby points of interest that enhance your adventure, making your vacation in Chestertown truly memorable.

• The Sagamore Golf Club: Located 8 miles from Chestertown, The Sagamore Golf Club offers a unique island resort experience. With its stunning views, pristine greens, and luxurious amenities, it's a perfect spot for golf enthusiasts and relaxation seekers alike.
• Friends Lake: Nestled within Chestertown, Friends Lake is ideal for those seeking romance and scenic beauty. Enjoy outdoor activities, picnicking by the water, or simply soaking in the picturesque beach vibes that make this lake a charming retreat.
• Loon Lake Beach: Also situated in Chestertown, Loon Lake Beach is a lovely spot to unwind. With its inviting beach atmosphere, it's perfect for sunbathing, swimming, or enjoying a leisurely stroll along the shore.

Best time to go to Chestertown

Visitor numbers in Chestertown is generally unchanged in popularity throughout the year. The best time to visit Chestertown is dependant 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	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

When planning your trip to Chestertown, New York, you have several airport options. Rutland Southern Vermont Regional Airport (RUT) is 44 miles away, with nearby hotels like Killington Mountain Lodge and Snowed Inn, both about 11 miles from the airport. Adirondack Regional Airport (SLK) is 54 miles from Chestertown, offering accommodations such as Hotel Saranac and Ampersand Bay Resort, located just 5 miles away. Floyd Bennett Memorial Airport (GFL) is the closest, at 24 miles, with great lodging options including Lodges At Cresthaven and Six Flags Great Escape Lodge, both within 9 miles. Each airport provides convenient access to Chestertown, making your travel planning easier.