Find hotels in Chestertown, NY from CA $86

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, offering skiing, scenic trails, and stunning lakes for exploration.
• Charming Beaches: Enjoy beautiful beaches and tranquil waters perfect for relaxation and recreation.
• Vibrant Live Music Scene: Experience the lively atmosphere with local music performances that reflect the community's spirit.
• Romantic Getaways: Ideal for couples, Chestertown provides a picturesque setting for a romantic retreat.
• Unique Accommodations: Stay in charming lodges or agritourism properties that offer comfort and local character.

Find great hotels near Chestertown

Chestertown, New York, offers a diverse selection of accommodations, from charming lodges to unique agritourism properties. Whether you're seeking an adventurous getaway, a family-friendly retreat, or a pet-friendly escape, you'll find a variety of options to suit your preferences. Explore the best and most affordable hotels in Chestertown, including the inviting Chester Inn, where comfort and local charm await you.

• Super 8 by Wyndham Lake George/Warrensburg Area: Super 8 by Wyndham Lake George/Warrensburg Area is a budget-friendly motel with a guest rating of 8.8, ideal for those seeking affordability without compromising comfort. Located 19.3km from Chestertown, this property is perfect for pet owners and business travellers. Amenities include pet-friendly policies, allowing dogs on-site, and a welcoming environment for service animals. Guests appreciate the convenient location for exploring the beautiful Lake George region while enjoying essential amenities such as free breakfast and complimentary Wi-Fi.
• The Alpine Lodge: The Alpine Lodge boasts a 3-star rating and a guest rating of 9.0, making it an excellent choice for couples and adventure seekers alike. Situated 16.1km from Chestertown, this lodge offers easy access to ski lifts and shuttle services, ideal for a winter getaway. With a focus on romance and adventure, guests can enjoy exciting activities like skiing, snowshoeing, and mountain climbing nearby. The lodge features special romance packages, including champagne service, ensuring a memorable experience for couples looking for a charming escape.
• North Creek Lodge at Gore Mountain: North Creek Lodge at Gore Mountain is a 3.5-star lodge with a guest rating of 8.7, catering to adventure lovers and pet-friendly travellers. Located 16.1km from Chestertown, this lodge offers a plethora of outdoor activities such as hiking, snowboarding, and cave exploring. With a welcoming pet policy in place, it's an excellent choice for those wishing to travel with their furry companions. The lodge provides essential amenities to ensure a comfortable stay, making it a great base for exploring the stunning Gore Mountain area.

Where to stay in and around Chestertown

Chestertown, New York, offers a perfect blend of outdoor adventure and romantic escapes. Nestled in a tranquil setting, visitors can explore nearby regions that provide lively atmospheres, family-friendly activities, and stunning beach areas. Whether you're seeking a secluded getaway or a central location buzzing with trendy spots, Chestertown and its surroundings promise a memorable travel experience for everyone.

• Bolton Landing: Situated 16.1km from Chestertown, Bolton Landing is a charming town that comes alive during the summer months, attracting visitors for its stunning natural beauty and outdoor activities. The area is known for its romantic ambiance, making it a perfect getaway for couples. Visitors can enjoy activities such as golfing at local private clubs, exploring scenic lake views, and unwinding at nearby beaches. The iconic island resorts enhance the picturesque landscape, offering a serene escape amidst nature.
• Brant Lake: A mere 4.8km from Chestertown, Brant Lake is a hidden gem that draws in outdoor enthusiasts year-round. The town's peak season runs from June to August, appealing to those seeking a scenic and romantic retreat. Visitors can indulge in skiing at nearby resorts and ski fields during the winter, while the summer months present opportunities for lakeside relaxation and exploration of the surrounding mountains. Brant Lake's tranquil atmosphere and breathtaking vistas make it an ideal spot for nature lovers.
• Chester Shores: Nestled around Chestertown, Chester Shores is a delightful neighborhood that offers a seasonal influx of visitors, particularly from July to September. This picturesque area is celebrated for its outdoor activities and scenic landscapes. Visitors can experience skiing at local resorts during the winter or explore the nearby lakes and mountains in warmer months. The parks in Chester Shores provide perfect spots for leisurely strolls and picnics, making it an inviting destination for families and couples alike.

Things to do in Chestertown

Chestertown, New York, offers a delightful escape for those seeking outdoor adventures and romantic getaways. You can enjoy skiing at nearby resorts, explore scenic trails, and immerse yourself in the vibrant live music scene. With a wealth of recreational opportunities, Chestertown is perfect for nature lovers eager to experience the stunning landscapes and the charm of small-town life.

Shopping

Chestertown offers charming local shops for unique gifts and souvenirs, including the Chestertown General Store. If you're up for a drive, head to the nearby town of Lake George, where you can explore the Lake George Outlets for a wider variety of shopping options.

Recreation

In Chestertown, the Adirondack Wellness Center provides rejuvenating yoga classes and holistic therapies amid serene surroundings. Nearby, the Lake George area offers hiking trails and kayaking for an invigorating outdoor experience, perfect for connecting with nature and enhancing your well-being.

Adventure

Explore the stunning natural beauty of the Adirondack Mountains by hiking the nearby trails, offering breathtaking views and diverse wildlife. For a thrilling experience, try white-water rafting on the Hudson River, where you can navigate exciting rapids while enjoying the scenic landscape.

Nightlife

Visit the charming Park Theatre for a cozy film night or enjoy a drink at the Chestertown Village Tavern, where you can mingle with locals and savour craft beers. For a lively atmosphere, check out a seasonal event at the nearby festival grounds.

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: Utilize Expedia’s search tool to customize your options based on your budget, preferred location, and desired hotel type. To find the most affordable prices and deals, arrange the price filter from low to high.
• Consider bundling your trip: You can save money by combining your hotel stay in Chestertown with flights and activities through an Expedia package.

Find the best attractions in and around Chestertown

Chestertown is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering stunning lakes, beautiful beaches, and charming island resorts. Visitors can enjoy a variety of activities that highlight the area's picturesque scenery, making it an ideal destination for anyone looking to immerse themselves in nature and relax by the water. Whether you're exploring the local landscape or unwinding at a resort, Chestertown has something for everyone.

• Friends Lake: Experience the serene beauty of Friends Lake, nestled in Chestertown. Enjoy outdoor activities, relax on the beach, or indulge in romantic picnics while taking in the stunning scenery that surrounds this tranquil spot.
• Loon Lake Beach: Loon Lake Beach offers a quintessential beach experience with its sandy shores and inviting waters. It’s the perfect place to unwind, sunbathe, or partake in water sports, making it a favourite among locals and visitors alike.
• The Sagamore Golf Club: Located 12.9km from Chestertown, The Sagamore Golf Club is a premier island resort featuring an exquisite golf course. Enjoy breathtaking views and a challenging game while being immersed in a truly luxurious 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	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. ALBany International Airport (ALB) is 101.4km away, with nearby hotels like The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 12.9km from the airport. Burlington International Airport (BTV) is 104.6km from Chestertown, offering hotel choices such as DoubleTree by Hilton Burlington Vermont, just 3.2km away. Plattsburgh International Airport (PBG) is 115.9km from Chestertown, with accommodations like Days Inn by Wyndham Plattsburgh, located 3.2km from the airport. Each hotel provides convenient access to their respective airports, ensuring smooth travel arrangements.