A waterfront town with a pier, dock, and several buildings.

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30 Sep - 1 Oct
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1 Oct - 2 Oct
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2 Oct - 4 Oct
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9 Oct - 11 Oct

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Our top choices for Chestertown hotels

1. Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
Chestertown
United States
John
SAR 657
SAR 729 total
includes taxes & fees
7 Oct - 8 Oct
Pine Tree Motel & Cabins

2. Friends Lake Inn

Friends Lake Inn
Chestertown
United States
Michael
SAR 488
SAR 542 total
includes taxes & fees
6 Oct - 7 Oct
Friends Lake Inn

3. The Fern Lodge

The Fern Lodge
Chestertown
United States
robert
SAR 1,505
SAR 1,671 total
includes taxes & fees
15 Oct - 16 Oct
The Fern Lodge

4. Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
Lake George
United States
Natalie
SAR 522
SAR 579 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Lake George

5. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
United States
Michaelangelo
SAR 527
SAR 718 total
includes taxes & fees
26 Oct - 27 Oct
Lodge at Schroon Lake

6. The Alpine Lodge

The Alpine Lodge
North Creek
United States
Richard
SAR 470
SAR 562 total
includes taxes & fees
27 Oct - 28 Oct
The Alpine Lodge

7. Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG
Lake George
United States
Tina
SAR 469
SAR 521 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Resort Lake George - Adirondack Area by IHG

8. Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George
Lake George
United States
Deborah
SAR 368
SAR 409 total
includes taxes & fees
7 Oct - 8 Oct
Comfort Inn & Suites Lake George

9. Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George
Lake George
United States
Mark
SAR 367
SAR 407 total
includes taxes & fees
29 Oct - 30 Oct
Hampton Inn & Suites Lake George

10. Lodges At Cresthaven

Lodges At Cresthaven
Lake George
United States
Robert
SAR 729
SAR 809 total
includes taxes & fees
19 Oct - 20 Oct
Lodges At Cresthaven

11. Depe Dene Lakeside Resort

Depe Dene Lakeside Resort
Lake George
United States
Jessica
SAR 368
SAR 409 total
includes taxes & fees
5 Oct - 6 Oct
Depe Dene Lakeside Resort

12. Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
Lake George
United States
Andrew
SAR 274
SAR 305 total
includes taxes & fees
5 Oct - 6 Oct
Super 8 by Wyndham Lake George/Warrensburg Area

13. Quality Inn Lake George

Quality Inn Lake George
Lake George
United States
Stephanie
SAR 415
SAR 460 total
includes taxes & fees
29 Oct - 30 Oct
Quality Inn Lake George

14. Gore Mountain Lodge

Gore Mountain Lodge
North Creek
United States
Henry
SAR 504
SAR 559 total
includes taxes & fees
20 Oct - 21 Oct
Gore Mountain Lodge

15. La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
Lake George
United States
Ilan
SAR 316
SAR 351 total
includes taxes & fees
18 Oct - 19 Oct
La Quinta Inn & Suites by Wyndham Lake George

16. Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets
Lake George
Canada
Philip
SAR 446
SAR 495 total
includes taxes & fees
4 Oct - 5 Oct
Spark by Hilton Lake George Outlets

17. Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Queensbury
United States
Brian
SAR 316
SAR 351 total
includes taxes & fees
27 Oct - 28 Oct
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

18. Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites
Lake George
United States
Rowell
SAR 348
SAR 400 total
includes taxes & fees
1 Oct - 2 Oct
Adirondack Retreat Inn & Suites

19. The Georgian Lakeside Resort

The Georgian Lakeside Resort
Lake George
United States
cait
SAR 377
SAR 418 total
includes taxes & fees
1 Oct - 2 Oct
The Georgian Lakeside Resort

20. The Juliana Resort

The Juliana Resort
Diamond Point
United States
Julia
SAR 345
SAR 383 total
includes taxes & fees
1 Oct - 2 Oct
The Juliana Resort
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Where to stay in Chestertown

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

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.

Stay near popular Chestertown attractions

Loon Lake

8.8/10 (8 reviews)
Loon Lake's crystal-clear waters provide a peaceful Adirondack Mountain retreat for outdoor enthusiasts. Rent a kayak to glide across the serene surface or cast a line for native fish from the sandy public beach.
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Friends Lake

9.4/10 (14 reviews)
This private Adirondack gem offers pristine waters and tranquil surroundings away from tourist crowds. Stay at Friends Lake Inn to access swimming, fishing, and kayaking in this exclusive 450-acre natural retreat.
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Loon Lake Beach

8.4/10 (7 reviews)
Loon Lake Beach offers crystal-clear waters against the backdrop of the Adirondack Mountains. Enjoy a day of swimming and picnicking in this serene natural setting, where sandy shores meet lush greenery.
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Tripp Pond

8.6/10 (4 reviews)
Tripp Pond offers a tranquil escape with calm waters surrounded by lush forests in Chestertown, New York. Enjoy peaceful fishing or kayaking while taking in the natural beauty of the Adirondack landscape.
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Learn more about Chestertown

Nestled in the Adirondacks, this charming town offers hiking trails and kayaking on Friends Lake during summer months. Winter visitors can hit the slopes at nearby Gore Mountain in North Creek or explore the Natural Stone Bridge and Caves in Pottersville.

See all hotels in Chestertown
A waterfront town with a pier, dock, and several buildings.

Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

8/10 Good
"The hotel is very well located, and the price-to-value ratio is excellent. The room was clean and comfortable, and the front desk staff was very friendly and helpful. The only minor inconvenience was the parking. The parking area was quite full, so we had to park in a spot that was a little far from our room. However, the parking was still within the hotel property, so it was not a major issue. Overall, we had a very pleasant stay and would definitely consider staying here again."
Maria 1-night trip
Posted 8 hours ago
Adirondack Retreat Inn & Suites
Super 8 by Wyndham Lake George/Downtown

Super 8 by Wyndham Lake George/Downtown

8/10 Good
"Clean"
Kenneth 1-night trip
Posted 16 hours ago
Super 8 by Wyndham Lake George/Downtown
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"It was clean and the bed was very comfy"
Carmen 2-night trip
Posted 2 days ago
Baymont by Wyndham Queensbury / Lake George
Surfside On The Lake

Surfside On The Lake

8/10 Good
"Hotel was great. Access to Lake and surrounding areas great. We were happy and although this may be a 3-star hotel, it provided a clean and satisfying experience."
Dominic 4-night trip
Posted 2 days ago
Surfside On The Lake
Nordick's Inn

Nordick's Inn

10/10 Excellent
"Great clean cheap motel :)"
Stephen 1-night trip
Posted 3 days ago
Nordick's Inn
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

8/10 Good
"Charming old fashion Adirondack rustic style / decor individual small cabins (also has motel-styled rooms) - parking either in front of rooms or between cabins, a couple of minutes outside Chestertown, NY, 30 minutes from Schroon Lake, and 45 minutes from Ticonderoga (StarTrek Museum & Fort). Very nice, friendly, and accomidating owners / operators. Breakfast / coffee place "Two Sparrows" 5 minutes down the road. Driveway very well lite / marked at night, although wish those lights had either dimmed or turned off post midnight for a better / darker sleep . . . As it was a very wet / rainy, and cold night - heat worked very qickly / well and found extra pillows and blanket. Plenty of hot water in sink / shower, soap, shampoo, small college refrigerator and microwave provided, however no hairdryer for partner . . . Did not test WiFi as we only stayed for 8 hours total time. Would have wished to have had more time to explore grounds and Chestertown itself."
Ralf 1-night trip
Posted 4 days ago
Pine Tree Motel & Cabins

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY
SAR 220
SAR 244 total
5 Oct - 6 Oct
includes taxes & fees
5.4/10 (1,008 reviews)
Days Inn by Wyndham Queensbury/Lake George
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY
SAR 277
SAR 308 total
1 Oct - 2 Oct
includes taxes & fees
7.6/10 Good! (1,122 reviews)
Baymont by Wyndham Queensbury / Lake George
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY
SAR 348
SAR 400 total
1 Oct - 2 Oct
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Adirondack Retreat Inn & Suites
The Georgian Lakeside Resort

The Georgian Lakeside Resort

384 Canada Street Lake George NY
SAR 377
SAR 418 total
1 Oct - 2 Oct
includes taxes & fees
The Georgian Lakeside Resort
Surfside On The Lake

Surfside On The Lake

400 Canada Street Lake George NY
SAR 329
SAR 459 total
21 Oct - 22 Oct
includes taxes & fees
8/10 Very Good! (844 reviews)
Surfside On The Lake
Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY
SAR 446
SAR 495 total
4 Oct - 5 Oct
includes taxes & fees
Spark by Hilton Lake George Outlets

Find out more about Chestertown

Top reasons to visit Chestertown

  • Outdoor Adventures: Chestertown is a haven for outdoor enthusiasts, offering activities like skiing, hiking, and exploring beautiful lakes and serene beaches.
  • Charming Atmosphere: The area boasts a relaxing ambiance, perfect for romantic getaways amidst picturesque landscapes.
  • Family-Friendly Fun: Enjoy diverse attractions, including an indoor waterpark, catering to families and adventure seekers alike.
  • Unique Accommodations: Choose from cozy lodges and agritourism experiences, ensuring a memorable stay in a beautiful setting.
  • Nearby Exploration: Discover nearby cities that offer trendy vibes and inviting spaces for recreation and relaxation.

Find great hotels near Chestertown

Discover the ideal hotel accommodations in Chestertown, New York, where adventure meets tranquility. Whether you're seeking a cozy lodge or a unique agritourism experience, Chestertown offers a range of pet-friendly and family-oriented options. Explore top-rated hotels that cater to your needs, ensuring a memorable vacation amidst stunning natural beauty. Read reviews and find the best lodgings to enhance your stay in this charming destination.

  • Super 8 by Wyndham Lake George/Warrensburg Area: A convenient and affordable motel option located 19.3km from Chestertown, Super 8 is perfect for travelers seeking a pet-friendly stay. This property caters to both leisure and business travelers, offering amenities designed for comfort and convenience. Guests appreciate the inclusive pet policy, allowing dogs and service animals, making it a welcoming choice for those traveling with furry companions. With its straightforward accommodations and essential amenities, Super 8 provides a practical base for exploring the beautiful Lake George area.
  • The Alpine Lodge: Nestled 16.1km from Chestertown, The Alpine Lodge is a charming 3-star retreat ideal for ski enthusiasts and couples seeking a romantic getaway. With access to ski shuttles and lifts nearby, adventure awaits just outside your door. The lodge offers a range of exciting activities such as snowshoeing, mountain biking, and rafting, ensuring an unforgettable experience. For those looking to celebrate a special occasion, the lodge provides romance packages, including champagne service to enhance your stay. Cozy and inviting, The Alpine Lodge is perfect for creating lasting memories.
  • North Creek Lodge at Gore Mountain: Situated 16.1km from Chestertown, North Creek Lodge at Gore Mountain is a 3.5-star lodge that caters to adventure-seekers. With a focus on outdoor activities, guests can enjoy skiing, snowboarding, hiking, and mountain climbing in the stunning natural surroundings. The lodge's proximity to various adventure sports ensures that thrill-seekers will find plenty to do. Whether you're exploring the great outdoors or relaxing in the comfortable lodge, North Creek Lodge provides an adventurous and welcoming atmosphere for all guests.

Where to stay near Chestertown

Chestertown, New York, is a hidden gem perfect for outdoor enthusiasts and romantic getaways. Explore the serene landscapes and enjoy a relaxing atmosphere while discovering nearby cities that offer trendy and family-friendly vibes. With attractions within walking distance of the city center, you'll find clean and inviting spaces for recreation and adventure. Make Chestertown your weekend getaway and immerse yourself in the beauty and charm of this picturesque region.

  • Brant Lake: Nestled a mere 4.8km from Chestertown, Brant Lake is a charming destination renowned for its stunning outdoor scenery and romantic ambiance. This city attracts visitors primarily during the summer months, from June to August, when outdoor enthusiasts flock to explore its ski resorts and fields. The local landscape is dotted with picturesque lakes, majestic mountains, and serene beaches, making it a perfect spot for relaxation and adventure alike. Whether you're skiing down the slopes or enjoying a peaceful day by the lake, Brant Lake offers a refreshing escape into nature.
  • Pottersville: Located 8.0km from Chestertown, Pottersville is a delightful city that captivates travelers with its scenic beauty and outdoor recreational opportunities. Peak visitor seasons align with the warmer months, particularly from June to August. Known for its charming parks and stunning waterfalls, Pottersville invites visitors to engage in various activities, including skiing at nearby resorts. The area's natural attractions, such as tranquil lakes, provide an idyllic backdrop for romantic getaways and family adventures alike, ensuring a memorable experience for all who visit.
  • Riparius: Just 9.7km from Chestertown, Riparius is an exciting city favored by adventure seekers and sports enthusiasts. The peak travel season occurs during the summer months, with visitors drawn to its thrilling ski fields and resorts. This city boasts a rich selection of outdoor activities, perfect for those looking to embrace the great outdoors. Nearby lakes, mountains, and parks offer a diverse range of experiences, from heart-pounding skiing adventures to tranquil nature strolls. Riparius is a must-visit for anyone seeking an exhilarating vacation filled with excitement and natural beauty.

Things to do near Chestertown

Chestertown is perfect for outdoor enthusiasts and romantic getaways, offering activities like skiing at nearby resorts and enjoying scenic views. You can explore fun activities, including an indoor waterpark for family fun and various outdoor recreation options, making it an ideal destination for adventure and relaxation alike.

Shopping

For a delightful shopping experience in Chestertown, visit local boutiques and unique shops. 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 and family-friendly vibes. The Shirt Factory, located 40.2km away, is another great option.

Recreation

At North Creek Ski Bowl Town Park, enjoy serene surroundings and outdoor activities that promote relaxation and wellness. Shepard's Beach Park offers a tranquil escape by the water, perfect for rejuvenation. For family fun, Around the World Miniature Golf provides an adventurous atmosphere for all ages.

Adventure

At Gore Mountain Ski Resort, located 16.1km from Chestertown, experience thrilling skiing on diverse slopes surrounded by breathtaking views. For a different thrill, visit the Adirondack Extreme Adventure Course, also 16.1km away, where you can zipline through the treetops and tackle exciting rope challenges.

Nightlife

Enjoy a romantic evening at Seagle Music Colony, just 19.3km away, for captivating performances. For family-friendly fun, visit Strand Theater, 20.9km out, showcasing delightful films. For adventure seekers, head to Fun Spot, 35.4km away, where excitement awaits in the arcade atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chestertown

To save money on your trip to Chestertown, consider visiting during the cheaper months of March to April or November, avoiding the peak summer season. Tuesdays are the best day for lower hotel rates, while Saturdays tend to be pricier. Utilize Expedia's search tools to compare room rates and find budget options, including eco-friendly accommodations. Booking a package with flights and activities can lead to significant savings. Don't forget to look for last-minute deals and exclusive discounts to make your visit even more affordable.

  • 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 makes it easy to choose your budget, desired location, and other preferences. You can sort the results to display prices from lowest to highest, allowing you to find the most affordable hotels right away. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and eco-friendly accommodations that you can book.
  • Consider bundling your trip: By booking an Expedia package, you can save money by combining your hotel accommodations in Chestertown with your flights and activities.

Find the best attractions in and around Chestertown

Chestertown is an ideal destination for those seeking outdoor adventures and romantic getaways. Visitors can explore beautiful lakes, serene beaches, and charming island resorts. The area offers a variety of attractions that cater to nature lovers and those looking for scenic experiences. Whether you want to relax by the water or hike through picturesque landscapes, Chestertown provides a perfect backdrop for a memorable vacation.

  • The Sagamore Golf Club: Nestled on an island, this exclusive golf club offers stunning views and a challenging course. Just 12.9km from Chestertown, its serene setting and luxurious amenities make it a perfect retreat for golf enthusiasts and relaxation seekers alike.
  • Loon Lake Beach: Located within Chestertown, Loon Lake Beach embodies the quintessential beach vibes. Enjoy sunbathing, swimming, or picnicking while taking in the picturesque surroundings. It's an ideal spot for families and friends to unwind by the water.
  • Natural Stone Bridge and Caves: About 11.3km from Chestertown, this attraction features breathtaking caves and stunning rock formations. Perfect for adventure lovers, it offers hiking trails and guided tours that showcase the natural beauty and geological wonders of the area.

Best time to go to Chestertown

The best time to visit Chestertown is dependent 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.3°F (-6.5°C)Light RainMostly CloudyAverageAverage
February22.3°F (-5.4°C)Light RainMostly CloudyAverageAverage
March30.4°F (-0.9°C)Light RainMostly CloudyAverageSlightly Low
April42.6°F (5.9°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.1°F (17.3°C)Light RainMostly SunnySlightly HighAverage
July69.1°F (20.6°C)Light RainMostly SunnySlightly HighSlightly High
August67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyAverageSlightly High
October48.6°F (9.2°C)Light RainMostly CloudySlightly LowAverage
November36.1°F (2.3°C)Light RainMostly SunnySlightly LowSlightly Low
December27.5°F (-2.5°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Chestertown

For your visit to Chestertown, New York, you can fly into several nearby airports. RUTland Southern Vermont Regional Airport (RUT) is 70.8km away, with hotel options like the 3.5-star Killington Mountain Lodge and Snowed Inn, both about 17.7km from the airport. Adirondack Regional Airport (SLK) is 86.9km away, offering stays at the 4-star Hotel Saranac, just 8.0km from the airport. Glens Falls Airport (GFL) is 38.6km away, with nearby hotels including the 4-star Lodges At Cresthaven and Six Flags Great Escape Lodge, located 9 and 8.0km away, respectively. Each of these airports provides convenient access to Chestertown.

Frequently asked questions

Where is the best place to stay in Chestertown?
Based on Expedia's traveler preferences, Pine Tree Motel & Cabins is a top place to stay in Chestertown. Two other choices for your visit to the area are Great Escape Lodge & Indoor Waterpark and La Quinta Inn & Suites by Wyndham Lake George. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best vacation rentals that Chestertown has to offer?
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: Visitors like this Chestertown vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Our travelers also rate Eagles Nest at Loon Lake near Gore Mountain as a favorite home for rent in Chestertown. See all vacation rentals in Chestertown.
If I need to cancel my hotel reservation in Chestertown, will I receive a refund?
Yes! You'll find that most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.
Where can I learn more about changing or cancelling my trip to Chestertown?
For more details about changing or cancelling your trip to Chestertown, head over to our customer service page.
What's the best LGBTQ-friendly place to stay in Chestertown?
Pine Tree Motel & Cabins is one of the top choices for those in the LGBT community.
What's the best pet-friendly accommodation in Chestertown?
What's the best hotel for a beach vacation in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach. See more stays near the beach in Chestertown.
What are some accommodations with pools in Chestertown?
La Quinta Inn & Suites by Wyndham Lake George: Hotel located near Great Escape. Features buffet, an indoor pool, and free self parking. Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool. and The Georgian Lakeside Resort are two additional hotels that feature an onsite pool. View all hotels with pools in Chestertown.
What's the most popular hotel in Chestertown with an on-site water park or a water park nearby?
What's the best hotel for staying near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Chestertown like?
Visitors to Chestertown are sure to enjoy the lakeside setting. Tourists can also enjoy the city's coffeehouses, forests, and seafood restaurants. In Chestertown, there are 115 hotels and other accommodations to choose from. Find out more about Chestertown.
What should I see while I'm in Chestertown?
Natural beauty is on display at Loon Lake Beach, Friends Lake, and Loon Lake. A couple of additional sights to add to your agenda are Hudson River and Tripp Pond. Check out what more to see and do in Expedia's Chestertown guide.
What's the weather like in Chestertown?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.