Chestertown, NY

Travel Guide

A waterfront town with a pier, dock, and several buildings.
A red bridge over a river with houses and greenery on both sides.
A snowy lodge with cabins and tall pine trees.

Where to stay in Chestertown

Find the best Chestertown areas and neighborhoods for the activities you enjoy most. Learn more about Chestertown
Learn more about Chestertown

Chester Shores

When in Chester Shores, you can plan a visit to Loon Lake Beach and Loon Lake, some noteworthy sights in the nearby area.

Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
$115 nightly
The price is $127 total per night from Nov 2 to Nov 3
$127 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ...
8.6/10 Excellent! (133 reviews)
"We stayed one night in October and there was no one there when we got there or when we checked. Also the pub was supposed to be open but no one was there either. I assume it is not like this in high season but it was not a good experience."

Reviewed on Oct 13, 2026

Friends Lake Inn
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ...
Get rates
Pine Tree Motel & Cabins
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Chestertown NY
Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a garden. Popular attractions Loon Lake Beach and Friends Lake are located ...
Get rates
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.
See all 1,628 properties in Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Chestertown NY
Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a garden. Popular attractions Loon Lake Beach and Friends Lake are located ...
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ...
Eagles Nest at Loon Lake near Gore Mountain
Lincoln Log Colony

Lincoln Log Colony

2 out of 5
2180 U.S. 9 Lake George NY
Stay at this cabin in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Fort William Henry Museum and Great Escape are located ...
8.8/10 Excellent! (28 reviews)
"We had a great time. Everyone was helpful and our lodge was clean."

Reviewed on Oct 13, 2026

Lincoln Log Colony
See all properties in Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Chestertown attractions

Loon Lake

8.8/10 (8 reviews)
Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.
See properties

Frequently asked questions

Is Chestertown worth visiting?
Chestertown is worth visiting for its appealing local dining scene, which features a range of North American and Italian cuisine. Travelers will also find practical transit options, with convenient bus access available for exploring the area.
When is the best time to visit Chestertown?
The best time to visit Chestertown is from May through September, when the climate is most pleasant for travelers to enjoy. For fewer crowds and better value, the quieter months of November through February are a good option, offering cooler weather and a more relaxed atmosphere.
What is Chestertown known for?
Chestertown is known for its scenic natural attractions, particularly Friends Lake and Loon Lake, which features Loon Lake Beach. Travelers can enjoy the outdoors here, alongside a local food scene that highlights North American food culture.
What is a good itinerary length for Chestertown?
A good itinerary length for Chestertown is one to two days to experience the natural beauty of Friends Lake, Loon Lake, and Loon Lake Beach. An extended stay of three to four days allows travelers to spend more time relaxing by the water and exploring the surrounding nature.
How do you get around Chestertown?
In Chestertown, travelers can get around using the local bus service. The primary point for bus travel is the Chestertown Bus Station, making it convenient to explore the area. For additional flexibility, taxis or rideshare services are also typically available.
What are the top things to do in and around Chestertown?
In and around Chestertown, travelers can enjoy the natural beauty of several local water bodies, including Friends Lake, Loon Lake, Loon Lake Beach, and Tripp Pond.
How do I plan a trip to Chestertown?
Plan your Chestertown trip by booking hotels and flights early on Expedia. Explore nature spots like Friends Lake, Loon Lake, and Loon Lake Beach. When planning outdoor activities, remember to have indoor backup options for weather flexibility. Consider a rental car for exploring the area and its dining, including North American, Italian, and seafood options.
What cuisines can you find in Chestertown?
In Chestertown you can find Italian cuisine, offering dishes like pasta, pizza, risotto, and tiramisu. Travelers can also enjoy North American comfort food, fresh seafood options, and Latin American choices such as Mexican tacos and burritos.
Can I book a refundable hotel in Chestertown?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chestertown by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chestertown with Expedia?
Expedia makes it easier to plan your Chestertown trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chestertown?
The best choice depends on your travel style. Hotels in Chestertown can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chestertown trip on Expedia?
Once you've booked your Chestertown trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chestertown trip?
Expedia offers customer support before, during, and after your Chestertown trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chestertown?
If it's your first trip to Chestertown, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chestertown hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chestertown hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Chestertown

An aerial view of a small island with dense forests, a large white mansion, and a dock with boats.

Bolton Landing

A river with clear water, surrounded by rocks and trees with autumn foliage.

North Creek

A sunset over a golden wheat field with distant mountains.

Warrensburg

A calm lake surrounded by dense forests with autumn foliage, under a cloudy sky.

Diamond Point

Explore a world of travel with Expedia