Find hotels in Chestertown, NY from £55

Top reasons to visit Chestertown

• Outdoor Activities: Chestertown is ideal for outdoor enthusiasts, featuring skiing, ice skating, and scenic trails for hiking and exploration.
• Charming Festivals: Experience local culture at the annual Chestertown Tea Party Festival and delightful fall festivals.
• Historic Attractions: Discover the charm and history of Historic Chestertown with its unique local attractions.
• Picturesque Lakes and Beaches: Enjoy the serene beauty of the town's lakes and beaches, perfect for relaxation.
• Diverse Accommodation Options: Choose from charming lodges and unique agritourism properties to suit every traveller's needs.

Find great hotels near Chestertown

Chestertown offers a delightful selection of lodgings, perfect for adventurous travellers, families, and pet owners alike. From charming lodges to unique agritourism properties, there’s something to suit every preference. Whether you’re seeking the best hotels or comfortable accommodation, you will find a variety of options that promise a memorable stay in this picturesque location.

• The Alpine Lodge: Nestled 6.2km from Chestertown, The Alpine Lodge offers a charming city-themed escape, perfect for adventure seekers and couples alike. This 3-star lodge is renowned for its comprehensive range of adventure sports, including skiing, kayaking, and hiking, ensuring an exhilarating stay. Guests can indulge in romantic packages featuring champagne services, ideal for creating memorable moments. With its prime location in the city centre, The Alpine Lodge provides easy access to both adventure and relaxation, making it a delightful choice for a romantic getaway.
• North Creek Lodge at Gore Mountain: Situated 6.2km from Chestertown, the North Creek Lodge at Gore Mountain is a 3.5-star lodge that caters to those with a thirst for adventure. With an array of outdoor activities available, such as mountain climbing, snowboarding, and hiking, this lodge is a haven for thrill-seekers. Its cosy atmosphere and proximity to adventure sports make it an excellent choice for those looking to immerse themselves in the great outdoors. The lodge's focus on adventure ensures that your stay will be filled with excitement and exploration.
• Gore Mountain Lodge: Located 6.2km from Chestertown, Gore Mountain Lodge is a convenient motel option catering to business travellers and nature enthusiasts. With easy access to ski shuttles and lifts, it is a fantastic base for those looking to hit the slopes. The motel also provides essential business amenities, including meeting rooms, making it suitable for corporate retreats. Surrounded by the beauty of nature, Gore Mountain Lodge combines practicality with a serene environment, ensuring a productive yet relaxing stay.

Where to stay in and around Chestertown

Chestertown, New York, offers a delightful blend of outdoor escapades and tranquil retreats. Wander through the scenic trails of the nearby Warrensburg area, or indulge in the charm of this quaint town, perfect for a romantic getaway. Just a stone's throw away, discover the family-friendly atmosphere and luxurious amenities that enhance your stay. Whether you seek adventure or relaxation, Chestertown provides an idyllic setting for your holiday.

• Brant Lake: Nestled a mere 1.9km from Chestertown, Brant Lake is a charming city known for its stunning outdoor experiences and picturesque scenery. This destination attracts visitors primarily during the summer months, from June to August, offering a romantic backdrop perfect for couples and families alike. Popular activities include skiing at the local ski resorts and enjoying the serene beauty of the lake, mountains, and beach nearby. The area’s natural landmarks provide ample opportunities for hiking and water sports, making Brant Lake a must-visit for outdoor enthusiasts.
• The Glen: Located within the Chestertown area, The Glen is a quaint village that beckons travellers looking for scenic views and outdoor adventures. With a moderate seasonal influx of visitors peaking in February and during the summer months, The Glen is perfect for those seeking a romantic getaway. The village features easy access to ski fields and resorts, as well as beautiful lakes, parks, and beaches that enhance its allure. Whether winter sports or summer relaxation is on your agenda, The Glen offers a delightful experience year-round.
• Pottersville: Situated 3.1km from Chestertown, Pottersville is a delightful city that combines outdoor beauty with romantic charm. Visitors flock here in the warmer months, particularly from June to August, to explore its stunning lakes, mountains, and parks. The city is renowned for its skiing opportunities, making it a popular destination for winter sports lovers. With its inviting atmosphere and a plethora of outdoor activities, Pottersville is an ideal location for those looking to enjoy nature and create lasting memories.

Things to do near Chestertown

Chestertown offers an idyllic setting for outdoor enthusiasts and couples alike, featuring activities such as skiing at local resorts and ice skating. Visitors can enjoy the annual Chestertown Tea Party Festival, delightful fall festivals, and serene picnic areas. This charming town is perfect for a romantic city break, allowing you to immerse yourself in its scenic beauty and vibrant community events.

Shopping

For shopping in Chestertown, visit local stores for unique gifts. If you're up for a drive, the Outlets at Lake George and Adirondack Outlet Mall, both 13.0km away, offer a lively shopping experience. The Shirt Factory, located 15.5km away, features various artisanal shops and galleries.

Recreation

At North Creek Ski Bowl Town Park, indulge in serene walks amidst nature and enjoy the tranquil atmosphere perfect for relaxation. Shepard's Beach Park offers a peaceful lakeside retreat, ideal for leisurely picnics. For a fun family outing, Around the World Miniature Golf provides a lively, adventurous vibe in a charming setting.

Adventure

Gore Mountain Ski Resort offers thrilling skiing experiences with stunning slopes, located 6.2km from Chestertown. For a dose of adrenaline, visit the Adirondack Extreme Adventure Course, a 10-mile journey filled with ziplines and rope challenges. Boreas Glades, 6.8km away, provides excellent skiing opportunities amidst beautiful scenery.

Nightlife

Experience the enchanting Seagle Music Colony for captivating performances, or catch a film at the Strand Theater for a romantic evening. For a family-friendly adventure, visit Fun Spot, an exciting arcade located a short drive away, ensuring a lively night filled with fun and entertainment.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the off-peak months of March to April or November, when accommodation prices are lower. Tuesdays tend to offer the best hotel rates, while Saturdays are typically the priciest. Use Expedia's search tool to compare room rates and find the best deals, including eco-friendly options. Additionally, consider bundling your hotel stay with flights and activities for extra savings. Walking is an excellent way to explore the charming town without incurring transport costs.

• 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 enables you to specify your budget and preferred location, among other criteria. You can organise your results to display prices from lowest to highest, allowing you to identify the most affordable hotels right away. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
• 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 and around Chestertown

Chestertown offers a delightful blend of outdoor adventures and scenic beauty, perfect for a romantic getaway. Visitors can explore its picturesque lakes, beaches, and island resorts. Don't miss the chance to visit Historic Chestertown, where you can discover local attractions that showcase the town's charm and history. Whether you seek tranquil landscapes or engaging activities, Chestertown promises a memorable experience for all types of travellers.

• Rogers Memorial Park Beach: Located 6.2km from Chestertown, this beach offers a perfect setting for relaxation and family fun. Enjoy the sandy shores and gentle waves, making it an ideal spot for sunbathing and picnicking amidst a picturesque backdrop.
• The Sagamore Golf Club: Situated 5.0km away, this exclusive island resort boasts a stunning golf course set against breathtaking scenery. It's a haven for golf enthusiasts, offering a luxurious experience with top-notch amenities and stunning views of the surrounding landscape.
• Friends Lake: Nestled within Chestertown, Friends Lake is renowned for its romantic ambience and breathtaking scenery. Ideal for outdoor activities like kayaking and hiking, it provides a tranquil escape surrounded by nature's beauty.

Best time to go to Chestertown

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	Slightly High
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	Average
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

Chestertown, New York, can be conveniently accessed via several nearby airports. Schenectady County Airport (SCH) is located 34.8km away, with hotel options including The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown. Rutland Southern Vermont Regional Airport (RUT) is 27.3km away, offering accommodation such as Killington Mountain Lodge and Snowed Inn. Finally, Adirondack Regional Airport (SLK) is situated 33.6km from Chestertown, with hotels like Hotel Saranac Curio Collection By Hilton and voco Saranac Lake NY Waterfront. Each airport provides various transport services to facilitate your journey from the hotels to the terminals.