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Top Chestertown hotels
Pine Tree Motel & Cabins
We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi.
Reviewed on Oct 5, 2025
The Queensbury Hotel
The room was very clean. Staff were friendly. The hotel looked fancy. The hotel had history, but was also modern. One of the best hotels we've stayed at.
Reviewed on Oct 20, 2025
Holiday Inn Resort Lake George - Adirondack Area by IHG
Bar and restaurant on site, walkable to the village area
Reviewed on Oct 20, 2025
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Very clean. Friendly. Good breakfast and coffee and tea/hot water available 24/7. Safe.
Reviewed on Oct 18, 2025
La Quinta Inn & Suites by Wyndham Lake George
Great pool
Reviewed on Oct 19, 2025
Friends Lake Inn
Staff was great. The inn is unique. Perfect!
Reviewed on Sep 7, 2025
The Georgian Lakeside Resort
My daughters and I we truly enjoyed staying here
Reviewed on Oct 16, 2025
Six Flags Great Escape Lodge & Indoor Waterpark
I come here yearly with my children. We usually go in the summer for 3 nights. We did not go this summer so we decided to spend one night in October. They had trick or treating for the kids, meet and greets with some characters, waterpark was great as usual!
Reviewed on Oct 19, 2025
Waterfront Home on Lake George w/ Boat Dock!
Chestertown Hotel & Travel Guide
Are you planning to spend some nights in Lake George? Need to reserve accommodation in the Chestertown area? You will discover 3 apartments and hotels on Travelocity within a 6-mile (10-kilometer) distance of the center of Chestertown.
Are you trying to track down somewhere to base yourself in 2 miles (3 kilometers) of the urban core of Chestertown? The Fern Lodge and Friends Lake Inn should be right up your alley.
It's worth having a look at the Holiday Inn Lake George Turf along with the The Alpine Lodge. The Holiday Inn Lake George Turf is located 16 miles (26 kilometers) away from the town center of Chestertown. The The Alpine Lodge, can be found just 9 miles (15 kilometers) away. If you'd prefer, you could make a booking at the Lake George Diamond Cove or the Hampton Inn & Suites Lake George.
Keen on checking out more of the forests this part of the country offers? Why don't you plan a few extra days in some of the other locations in Adirondack Region? If you throw yourself at common hobbies, like, for example, snowboarding, skiing and cross-country skiing, or instead rather travel around to explore the landmarks, you will easily find appropriate lodgings around here.
Glens Falls is 25 miles (39 kilometers) south of Chestertown and features Charles R. Wood Theater and Hyde Collection. A few Glens Falls rooms include the The Glens Falls Inn and Sleep Inn & Suites. 20 miles (35 kilometers) to the south of Chestertown, you'll also find Queensbury, home to the Six Flags Great Escape Lodge & Indoor Waterpark and Country Inn & Suites By Carlson. The Fun Spot and SUNY Adirondack are some of the more popular points of interest to discover for those visiting Queensbury.
Before you leave Lake George, make sure you join locals to watch an exciting game. Stop by Saratoga Race Course, found south of Chestertown. Modern visitors that would like the convenience of booking a room in the area, reserve a room in the Saratoga Arms or Residence Inn by Marriott Saratoga Springs.
After you've got to know what hotel options are available in Chestertown, be sure to read through our Chestertown area guide for information on ways to spend your time around here.
Top reasons for your vacation to Chestertown
- Loon Lake Beach: Enjoy a day of swimming, sunbathing, and picnicking at the stunning Loon Lake Beach.
- Saratoga Springs: Experience the vibrant atmosphere and charming downtown area of Saratoga Springs.
- Hiking and Canoeing: Explore scenic forests and lakes by hiking and canoeing in the Saratoga area.
- Downtown Chestertown: Indulge in delicious seafood, relax at the marina, or go horseback riding in the center of downtown Chestertown.
- Wilmer Park and Boat Docks: Unwind in nature and enjoy stunning views at Wilmer Park and the boat docks in Chestertown.
Find your favorite hotels in Chestertown
If you're planning an outdoor vacation in Chestertown, New York, you'll find a variety of hotel accommodations to choose from. Whether you prefer a cozy bed and breakfast or a luxurious resort, there are options available to suit every traveler's needs. With its scenic surroundings and proximity to outdoor activities, Chestertown is a great destination for nature lovers and outdoor enthusiasts. Make the most of your stay by choosing one of the best hotels in Chestertown.
| Hotel name | Type | Stars | Description |
| Friends Lake Inn | Hotel | 4.0 | This 4.0-star hotel is an excellent option for your outdoor vacation. With close proximity to activities like snowtubing, rowing, canoeing, snowshoeing, snowmobileriding, fishing, sledding, rafting, and crosscountryskiing, you'll have plenty to keep you entertained. The hotel offers comfortable accommodations and a range of facilities to make your stay enjoyable. |
| The Fern Lodge | Bed & breakfast | 3.5 | If you're looking for a cozy bed & breakfast, The Fern Lodge is a great choice. This 3.5-star rated lodge is located near a lake and offers easy access to activities like snowtubing, rowing, canoeing, snowshoeing, snowmobileriding, sledding, rafting, and crosscountryskiing. Enjoy a comfortable stay and a charming atmosphere. |
| Pine Tree Motel & Cabins | Motel | 2.0 | For a more budget-friendly option, the 2.0-star rated Pine Tree Motel & Cabins is a good choice. With close proximity to basketball, smoking, sports, beach, recreation, petfriendly, tours, familyfriendly, freeparking, and coffee, this motel offers convenient facilities for your outdoor vacation. |
Explore the best activities and sights in Chestertown
Chestertown, located in beautiful upstate New York, is an ideal destination for a family outdoor vacation. With its close proximity to lakes, forests, and secluded areas, there are plenty of activities to engage in. Families can enjoy canoeing and horseback riding, or spend a relaxing day by the marina, boating and indulging in delicious seafood. Chestertown also offers hiking trails and easy access to Lake George, providing endless opportunities for outdoor exploration. Don't miss the boat docks and Wilmer Park, which offer stunning views and a chance to unwind in nature.
- Loon Lake Beach: This picturesque beach offers a unique experience with its sandy shores, crystal-clear waters, and breathtaking views of the surrounding mountains. Relax under the warm sun, take a refreshing swim, or build sandcastles with your family. The beach is perfect for beachgoers looking to unwind and soak up the natural beauty. Enjoy picnics on the shore or explore the nearby trails for a peaceful hike. Loon Lake Beach is the ideal destination for a fun-filled beach experience surrounded by stunning scenery.
- Loon Lake: Nestled amidst coffee-colored forests, Loon Lake is a hidden gem that promises a secluded and enchanting experience. The tranquil lake offers opportunities for canoeing, horseback riding, and boating, allowing visitors to immerse themselves in nature's beauty. Enjoy the peacefulness of the lake as you indulge in a relaxing day of fishing or take a leisurely stroll along the shoreline. The marina offers boating enthusiasts the chance to explore the serene waters, while seafood lovers can savor fresh and delicious dishes. Loon Lake provides a captivating and romantic setting, perfect for those seeking a peaceful and scenic outdoor getaway.
- Friends Lake: Surrounded by coffee-colored forests, Friends Lake is a serene retreat that offers a unique and secluded experience. The tranquil lake is perfect for canoeing, horseback riding, and boating, allowing visitors to immerse themselves in the beauty of nature. Relax on the shores and take in the breathtaking scenery or explore the nearby trails for a peaceful hike. The marina provides opportunities for boating enthusiasts to explore the calm waters, while seafood lovers can indulge in delicious dishes. Friends Lake offers a romantic and picturesque setting, ideal for those seeking a scenic and outdoor escape.
Where to stay in Chestertown
Get ready for an outdoor adventure in Chestertown, New York! Located near the stunning Loon Lake Beach, you and your family can enjoy a day of swimming, sunbathing, and picnicking by the water. For a taste of city life, head to Saratoga Springs, known for its vibrant atmosphere and charming downtown area. Explore the Saratoga area by hiking through scenic forests or canoeing in a nearby lake. And don't forget to visit the center of downtown Chestertown, where you can indulge in delicious seafood, relax at a marina, or go horseback riding. Get ready for a memorable outdoor vacation!
- Chester Shores: Chester Shores is a picturesque neighborhood that offers a unique outdoor experience for families. Situated in the heart of Chestertown, this region boasts stunning lakeside views and serene natural surroundings. Families can enjoy a wide range of activities such as boating, fishing, and swimming in the crystal-clear waters of the lake. The area also has well-maintained hiking and biking trails, allowing families to explore the beautiful landscape at their own pace. With its charming atmosphere and local affinities, Chester Shores provides the perfect setting for a relaxing and adventurous outdoor vacation.
The travel seasons of Chestertown
Trips to Chestertown show no change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from October to December, and November sees the least travelers.
Chestertown has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 69.1 degrees Fahrenheit. The wettest month in Chestertown is June, so pack accordingly.
 Calendar Month |  Temperature |  Precipitation |  Cloudiness |
| January | 20.3°F (-6.5°C) | Light Rain | Mostly Cloudy |
| February | 22.3°F (-5.4°C) | Light Rain | Mostly Cloudy |
| March | 30.4°F (-0.9°C) | Light Rain | Mostly Cloudy |
| April | 42.6°F (5.9°C) | Light Rain | Mostly Cloudy |
| May | 55.9°F (13.3°C) | Light Rain | Mostly Sunny |
| June | 63.1°F (17.3°C) | Light Rain | Mostly Sunny |
| July | 69.1°F (20.6°C) | Light Rain | Mostly Sunny |
| August | 67.1°F (19.5°C) | Light Rain | Mostly Sunny |
| September | 60.3°F (15.7°C) | Light Rain | Mostly Sunny |
| October | 48.6°F (9.2°C) | Light Rain | Mostly Cloudy |
| November | 36.1°F (2.3°C) | Light Rain | Mostly Sunny |
| December | 27.5°F (-2.5°C) | Light Rain | Mostly Cloudy |
Food and dining in Chestertown
While visiting Chestertown, New York, you will have the opportunity to indulge in some delicious local cuisine. One highly rated and popular restaurant is The Bullhouse, which specializes in Latin American dishes. Another great option is Friends Lake Inn, known for its delectable North American cuisine. If you're in the mood for a traditional American pub experience, check out Public House. For a taste of the sea, be sure to try the crab soup at Crossroads Deli. Downtown House Chestertown offers a variety of flavorful dishes, and you can't miss the chance to try some locally produced maple syrup.
How do I find a great hotel with Travelocity?
Ensure your entire crew enjoys an unforgettable vacation with our reliable and all-round online travel platform. Discover the perfect accommodations for your family by using our family-friendly badge, which identifies hotels that offer extra amenities for children. Our custom filters allow you to narrow down your options to hotels that are closest to top attractions, offer enhanced cleaning services, and fit within your price range.
Why should I book with Travelocity?
Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules call for trips that are headache-free. Our aim is to provide stress-free travel every time you and your family book with us so that you can spend less time worrying and more time creating cherished memories. With our assistance, you can discover and plan your ideal trip while benefiting from transparent pricing, reliable reviews, and round-the-clock customer support before, during, and after your vacation.
How can I save money on my trip to Chestertown?
When planning your trip to Chestertown, consider visiting during the less popular season from October to December to save money. Another way to save is by combining your flights, hotel, and car bookings as a bundle at a discounted price. While in Chestertown, take advantage of the inexpensive local attractions such as exploring the nearby forests, enjoying a relaxing day by the lake, and trying delicious seafood. These activities offer affordable options for family fun in Chestertown, New York.
Frequently asked questions
Recent Chestertown hotel reviews by fellow wanderers
The Queensbury Hotel
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