Find hotels in Chestertown, NY from CA $63

Top reasons to visit Chestertown

• Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, offering skiing, hiking, and scenic exploration.
• Charming Lakes and Beaches: Enjoy stunning lakes and inviting beaches, perfect for relaxation and recreation.
• Romantic Getaways: The picturesque setting makes it an ideal destination for couples looking for a romantic retreat.
• Unique Accommodations: Choose from cozy lodges and agritourism properties to enhance your stay.
• Festivals and Events: Participate in local holiday events and festivals for a taste of community spirit.

Find great hotels near Chestertown

Explore a variety of lodging options in Chestertown, New York, where you can find cozy lodges and unique agritourism properties. Ideal for adventurous families and pet-friendly getaways, Chestertown offers a range of hotels and vacation rentals. Whether you're seeking luxurious rooms or spacious suites, you'll discover the perfect accommodation to enhance your stay in this charming destination.

• Super 8 by Wyndham Lake George/Warrensburg Area: This motel is an ideal choice for business travellers seeking a pet-friendly environment. Located 19.3km from Chestertown, it offers practical amenities tailored for professionals, including business services and facilities. The motel is accommodating to pets, allowing dogs on the premises, which is perfect for those travelling with furry companions. The service animal fee is waived, ensuring a stress-free experience. With its convenient location, guests can enjoy easy access to local attractions while enjoying a comfortable and budget-friendly stay.
• The Alpine Lodge: Nestled 16.1km from Chestertown, The Alpine Lodge is a charming 3-star accommodation perfect for those seeking adventure and romance. This lodge offers a plethora of outdoor activities such as skiing, hiking, and kayaking, making it a favourite for adventure enthusiasts. For couples, romance packages enhance the experience, featuring amenities like champagne service to celebrate special moments. Its city-centre location allows guests to explore local attractions easily. The Alpine Lodge combines thrilling activities with romantic touches, ensuring a memorable getaway.
• North Creek Lodge at Gore Mountain: Positioned 16.1km from Chestertown, North Creek Lodge at Gore Mountain is a 3.5-star lodge that caters to adventure seekers. With a range of outdoor activities available, including hiking, snowboarding, and mountain climbing, it's a perfect base for those looking to explore the great outdoors. The lodge's proximity to Gore Mountain makes it an ideal choice for winter sports enthusiasts. Guests will appreciate the comfortable accommodations that provide a restful retreat after a day of adventure, ensuring an exhilarating stay in a scenic location.

Where to stay in and around Chestertown

Chestertown, New York, offers a picturesque escape perfect for outdoor enthusiasts and couples alike. Surrounded by stunning scenery, this charming town is ideal for a weekend getaway or a romantic retreat. Nearby, explore family-friendly adventures and trendy recreation options that cater to all tastes. Embrace the relaxing atmosphere of Kent County, where you can unwind and create lasting memories in a serene setting.

• Brant Lake: Nestled only 4.8km from Chestertown, Brant Lake is a picturesque destination that draws visitors with its stunning outdoor scenery and romantic ambiance. This city is particularly popular during the summer months, from June to August, when the natural beauty of the lake and mountains comes alive. Outdoor enthusiasts can enjoy a range of activities such as skiing in the winter and basking on the beach in the warmer months. Brant Lake’s ski resorts and fields are perfect for adventurous travellers looking to hit the slopes. Don’t miss the chance to explore the serene lakeside, where breathtaking views await.
• The Glen: A charming village located within the Chestertown area, The Glen is a delightful spot for those seeking a blend of outdoor adventure and romantic settings. Just like its neighbouring areas, The Glen experiences a seasonal influx of visitors, peaking from June to August. Here, you can enjoy skiing at local resorts during winter or relaxing at the nearby beaches and parks during summer. The village's natural surroundings provide an inviting atmosphere, making it ideal for leisurely strolls and picnics amidst nature’s beauty.
• Chester Shores: Situated around Chestertown, Chester Shores is a tranquil neighbourhood that offers a serene escape for those who appreciate the great outdoors. The area welcomes a seasonal crowd, especially during the summer months. Chester Shores is known for its scenic landscapes, including lakes, beaches, and mountains, making it a perfect spot for romantic getaways. Visitors can partake in various activities like skiing and enjoying the picturesque surroundings. With its inviting atmosphere and proximity to nature, Chester Shores promises a memorable experience for all who visit.

Things to do near Chestertown

Chestertown, New York, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy skiing at local resorts, exploring scenic landscapes, and participating in holiday events and festivals. Don't miss the chance to embark on house tours and engage in various outdoor activities that showcase the area's natural beauty and charm.

Shopping

In Chestertown, you can enjoy local shops for unique gifts. If you're up for a drive, the Outlets at Lake George and Adirondack Outlet Mall, both 33.8km away, offer a variety of stores in a fun, family-friendly atmosphere. The Shirt Factory, located 40.2km away, features local artisans and crafts.

Recreation

North Creek Ski Bowl Town Park offers a tranquil setting with wellness vibes, perfect for relaxation and outdoor activities, located 16.1km from Chestertown. Shepard's Beach Park, 25.7km away, features serene beach relaxation. For family fun, Around the World Miniature Golf, 27.4km away, combines adventure and sports.

Adventure

Experience thrilling skiing at Gore Mountain Ski Resort, located 16.1km from Chestertown, where you can enjoy pristine slopes and vibrant sports energy. For an adrenaline rush, head to Adirondack Extreme Adventure Course, also 16.1km away, featuring exhilarating ziplines and challenging rope courses amidst stunning outdoor scenery.

Nightlife

Experience the vibrant nightlife in Chestertown by visiting the Seagle Music Colony for a delightful theatre performance, or catch a film at the Strand Theater for a romantic evening. For a fun-filled adventure, head to the Adventure Racing Family Fun Center, perfect for the whole family.

Booking tips and Expedia advantages for Chestertown

When planning your trip to Chestertown, New York, consider visiting during January, March, or November for lower accommodation rates. Tuesdays are typically the least expensive days to stay, while Saturdays are the most costly. Use Expedia to compare prices and book packages that combine flights and activities for better savings. Explore free outdoor activities in the area, and take advantage of local public transport options to cut travel costs. By planning your visit during the off-peak season and refining your search for budget-friendly accommodations, you can enjoy a more affordable vacation.

• 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: Utilize Expedia's search tool to refine your options based on your budget, desired location, and preferred type of accommodation. To find the most affordable prices and offers, simply arrange the price filter from lowest to highest.
• 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, New York, offers a picturesque setting for outdoor enthusiasts and couples seeking a romantic getaway. With its stunning lakes, charming beaches, and inviting island resorts, the area is perfect for those looking to immerse themselves in nature. Visitors can enjoy a variety of scenic experiences, making it an ideal spot for relaxation and adventure alike. Whether you’re exploring Chestertown or nearby attractions, there’s no shortage of memorable activities to partake in.

• The Sagamore Golf Club: Nestled on an island resort 12.9km from Chestertown, The Sagamore Golf Club offers a unique golfing experience surrounded by stunning views of the Adirondacks and serene waters. Play a round of golf while enjoying the luxury amenities of the resort, making it a perfect spot for relaxation and recreation.
• Friends Lake: Located within Chestertown, Friends Lake is a picturesque spot ideal for outdoor activities. With its beautiful beach and scenic views, it provides a romantic atmosphere for couples and a tranquil retreat for families looking to enjoy nature.
• Natural Stone Bridge and Caves: Just 11.3km from Chestertown, this adventure-filled site features impressive caves and unique rock formations. Explore the natural beauty and engage in outdoor activities, making it a perfect destination for thrill-seekers and nature lovers alike.

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	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

If you're planning a visit to Chestertown, New York, the nearest major airports are Rutland Southern Vermont Regional (RUT) and Adirondack Regional (SLK). Rutland is located 70.8km from Chestertown, with nearby hotels like Killington Mountain Lodge and Killington Grand Hotel, both offering convenient accommodations. Saranac Lake Airport is 86.9km away, with excellent options such as Hotel Saranac and Ampersand Bay Resort. Lake Placid Airport (LKP) is 69.2km distant, featuring fine lodgings like The Whiteface Lodge and High Peaks Resort. These airports provide various transportation services to ensure a smooth journey to Chestertown.