Find hotels in Chestertown, NY from CA $59

Top reasons to visit Chestertown

• Outdoor Recreation: Chestertown offers a plethora of outdoor activities, including skiing, snowmobiling, and exploring the scenic Centennial Trail.
• Beautiful Lakes and Beaches: The area boasts stunning lakes and relaxing beaches, perfect for water-based activities and enjoying nature.
• Historic Downtown: Stroll through the charming downtown filled with quaint shops and picturesque views.
• Diverse Accommodations: Choose from cozy lodges, unique castle stays, and budget-friendly options to suit every traveller.
• Live Music and Tours: Experience local culture with live music events and various vacation tours for a vibrant atmosphere.

Find great hotels in Chestertown

Discover a variety of hotel accommodations in Chestertown, New York, catering to every traveler's needs. Whether you're seeking a cozy lodge, a unique castle stay, or budget-friendly options, Chestertown has it all. Enjoy family-friendly amenities, pet-friendly services, and adventure-themed experiences that make for an unforgettable getaway. With a range of ratings from 2 to 4.5 stars, you'll find the best hotels to suit your preferences and ensure a memorable vacation.

• Super 8 by Wyndham Lake George/Warrensburg Area: Located 19.3km from Chestertown, Super 8 by Wyndham Lake George/Warrensburg Area is a cozy motel catering to both business and pet-friendly travellers. With a focus on convenience, this property offers essential services for business guests, ensuring a productive stay. Additionally, it welcomes pets, making it an ideal choice for those who wish to travel with their furry companions. With amenities such as a waived fee for service animals and a pet policy that allows dogs, guests can enjoy their vacation without leaving their pets behind.
• The Alpine Lodge: Situated 16.1km from Chestertown, The Alpine Lodge is a charming 3-star lodge perfect for those seeking a romantic getaway, adventure, or a skiing holiday. With ski shuttles and lifts nearby, it's an excellent base for winter sports enthusiasts. The lodge also offers a variety of adventure sports, including cave exploring and horse riding. For couples, romance packages with champagne service provide a delightful touch, ensuring an unforgettable experience amidst the stunning alpine scenery.
• North Creek Lodge at Gore Mountain: Just 16.1km from Chestertown, North Creek Lodge at Gore Mountain is a 3.5-star lodge designed for adventure seekers. With a broad range of outdoor activities available, such as mountain climbing, snowboarding, and hiking, this lodge is ideal for those looking to embrace the great outdoors. Its proximity to various adventure sports ensures that thrill-seekers will find plenty to keep them occupied during their stay, making it a fantastic choice for an action-packed holiday.

Where to stay in Chestertown

Chestertown, New York, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Explore the historic downtown, with its quaint shops and scenic views, while experiencing the relaxing vibes of the surrounding areas. Just a short drive away, enjoy the luxury and recreation offered by the beautiful Chesapeake Bay. Whether you're seeking tranquility or trendy spots, Chestertown and its nearby regions promise a delightful vacation experience.

• Chester Shores: Nestled around the picturesque Chestertown, Chester Shores is a charming neighborhood that attracts visitors year-round, with peak seasons from July to September. This area is ideal for those seeking outdoor adventures, romantic getaways, and stunning scenery. Whether you're eager to hit the slopes at nearby ski resorts or enjoy relaxing days by the lake, Chester Shores offers a variety of activities. Local landmarks include beautiful beaches and majestic mountains, perfect for exploring nature's beauty.
• The Glen: The Glen is a quaint village situated within the Chestertown area, known for its seasonal charm and outdoor experiences. Like Chester Shores, it sees a surge of tourists from July to September. Visitors flock here for romantic escapes and to bask in the scenic landscapes. The Glen provides access to excellent skiing opportunities, with ski fields and resorts nearby. Enjoy the local parks, which serve as perfect picnic spots, and take in the vibrant atmosphere as you explore this delightful village.
• Brant Lake: Located approximately 4.8km from Chestertown, Brant Lake is a lively city that draws visitors for its stunning outdoor experiences and natural beauty. Peak visitation occurs from June to August, making it a popular summer destination. Brant Lake offers thrilling skiing adventures, with ski resorts and fields that cater to enthusiasts of all skill levels. The area is home to breathtaking lakes, scenic mountains, and sandy beaches, making it a perfect spot for both relaxation and recreation amidst nature.

Things to do in Chestertown

Chestertown, New York, is a charming destination ideal for outdoor enthusiasts and romantic getaways. Visitors can enjoy skiing at local resorts, exploring the scenic Centennial Trail, and participating in snowmobile tours. The area also features live music and various vacation tours, making it a perfect spot for outdoor recreation and relaxation amidst beautiful landscapes.

Shopping

Chestertown offers charming local shops for unique gifts and souvenirs. If you're up for a drive, the Outlets at Lake George and Adirondack Outlet Mall, both 20-33.8km away, provide a variety of shopping options for everyone. The Shirt Factory, located 40.2km away, is also worth a visit.

Recreation

At North Creek Ski Bowl Town Park, enjoy serene nature walks and relaxation amidst stunning landscapes, just 16.1km from Chestertown. Shepard's Beach Park, located 25.7km away, offers tranquil lakeside spots for meditation. For family fun, Around the World Miniature Golf, 27.4km distant, combines adventure and sports in a vibrant setting.

Adventure

Gore Mountain Ski Resort, located 16.1km from Chestertown, offers exhilarating skiing experiences amidst breathtaking landscapes. For those seeking thrills, the Adirondack Extreme Adventure Course, also 16.1km away, features an exciting zipline and ropes course set in the great outdoors. Sagamore Glades, 16.1km from town, provides fantastic skiing opportunities.

Nightlife

In Chestertown, Seagle Music Colony offers a romantic theatre experience just 19.3km away, while the Strand Theater provides family-friendly cinematic adventures 20.9km away. For a bit of excitement, head to Fun Spot, an arcade and adventure zone located 35.4km from Chestertown, perfect for family fun.

Booking tips and Expedia advantages for Chestertown

Chestertown, New York, offers several budget-friendly options for tourists. Enjoy free activities like swimming at Loon Lake Beach or relaxing at Friends Lake. Consider visiting during the cheaper months of March to April or November, with Tuesday being the least expensive day to stay. Use Expedia to find eco-friendly hotels and compare rates, sorting by price to find the best deals. Bundling your hotel, flights, and activities can also save you money. With thoughtful planning, you can enjoy Chestertown without breaking the bank.

• 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, desired location, and preferred type of accommodation. For instance, selecting the "Eco-certified" filter will highlight sustainable and environmentally-friendly hotels currently available. To find the best prices and offers, 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.

Find the best attractions in 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 to bask in nature or enjoy water-based activities, Chestertown provides a delightful experience for travellers eager to connect with the great outdoors and soak in the area's picturesque landscapes.

• Friends Lake: Nestled in Chestertown, Friends Lake offers a picturesque setting perfect for romance and outdoor activities. Enjoy serene beach vibes while taking in the stunning scenery, making it an ideal spot for relaxation or a romantic getaway.
• The Sagamore Golf Club: Located 12.9km from Chestertown, this exquisite island resort boasts a stunning golf course and luxurious amenities. Experience world-class golfing amidst beautiful landscapes, making it a perfect retreat for golf enthusiasts.
• Loon Lake Beach: Situated in Chestertown, Loon Lake Beach invites you to unwind on its sandy shores. Enjoy the refreshing lake waters and laid-back beach vibes, perfect for sunbathing, swimming, and family fun.

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	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 your visit to Chestertown, New York, you can fly into several major airports. Rutland Southern Vermont Regional Airport (RUT) is located 70.8km away, with nearby hotels such as Killington Mountain Lodge and Snowed Inn, both 17.7km from the airport. Adirondack Regional Airport (SLK) is 86.9km away, offering options like Hotel Saranac and The Point, situated 5 and 12.9km away, respectively. Lastly, Lake Placid Airport (LKP) is 69.2km from Chestertown, with excellent accommodations like The Whiteface Lodge and High Peaks Resort, both just 3.2km from the airport. Each airport provides convenient access to Chestertown and comfortable lodging nearby.