Photo by Julie Miller

Find hotels in Chestertown, NY from ₩84,885

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Compare 1,491 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
Lodge at Schroon Lake
2.0 star property
8.8 out of 10, Excellent, (138)
"Walking distance to dining options that have more budget friendly price"
The price is ₩161,630
₩216,651 total
includes taxes & fees
May 15 - May 16
Lodge at Schroon Lake
Exterior
Pine Tree Motel & Cabins
2.0 star property
9.0 out of 10, Wonderful, (113)
"Cutest cabins, friendly owners, dog friendly ❤️ supporting small businesses definitely going back next year. "
The price is ₩239,402
₩265,736 total
includes taxes & fees
May 16 - May 17
Pine Tree Motel & Cabins
Exterior
Best Western Plus Ticonderoga Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (590)
"Everything was good except the person in the front desk was no really nice when I arrived, I don’t know she say is not room clean and was 8pm!"
The price is ₩255,804
₩289,060 total
includes taxes & fees
May 20 - May 21
Best Western Plus Ticonderoga Inn & Suites
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Standard Room, 1 Bedroom, Non Smoking (two full) | Free WiFi, bed sheets
Circle Court Motel
2.5 star property
8.6 out of 10, Excellent, (176)
"Way to go for a short fishing trip in Ticonderoga. Great place with many advantages for having a bassboat"
The price is ₩131,329
₩148,402 total
includes taxes & fees
May 15 - May 16
Circle Court Motel
Exterior
Super 8 by Wyndham Ticonderoga
2.5 star property
8.0 out of 10, Very Good, (890)
"Perfect stop for our trip to VT for the eclipse. Gym was great way to start moving again after hours in the car!"
The price is ₩115,118
₩130,084 total
includes taxes & fees
Jun 2 - Jun 3
Super 8 by Wyndham Ticonderoga
Deluxe Cabin | Individually decorated, individually furnished, laptop workspace
Maple Leaf Motel
2.5 star property
8.6 out of 10, Excellent, (314)
"This is my second stay here. It's a charming place and a good value. The rooms are large and the beds are comfortable. It's definitely dated but I really like this place. "
The price is ₩176,473
₩199,415 total
includes taxes & fees
May 16 - May 17
Maple Leaf Motel
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
9.6 out of 10, Exceptional, (14)
"John and Yvonne were the perfect hosts hosts...Tvicolorfulsunse"
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Luxury Studio Suite, 1 King Bed, Lake View (#1) | Lake view
Chateau Rooms
4.5 star property
9.2 out of 10, Wonderful, (38)
"The owner upgraded our room so we were facing Lake George. Our room was beautiful with a balcony. We sat in the room and watched three deer by the lake. The manager was very prompt and helpful with a small issue we had. "
Chateau Rooms
Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn
4.0 star property
9.0 out of 10, Wonderful, (77)
"The food was made to order and very good prices were fair. The cost to stay there is overpriced."
The price is ₩385,806
₩428,242 total
includes taxes & fees
May 16 - May 17
Friends Lake Inn
Restaurant
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (42)
"Paradise just simply heavenly. And so well appointed. Feel so at home"
The price is ₩819,370
₩909,499 total
includes taxes & fees
May 26 - May 27
The Fern Lodge
Front of property - evening/night
Boathouse Waterfront Lodging
3.5 star property
9.4 out of 10, Exceptional, (17)
"Fantastic views and premium lake access. Close enough to walk to great coffee, food, shops. We loved it and will com back!"
Boathouse Waterfront Lodging
Exterior
Silver Bay Inn and Conference Center
3.0 star property
9.6 out of 10, Exceptional, (37)
"Excellent "
The price is ₩115,058
₩127,714 total
includes taxes & fees
May 16 - May 17
Silver Bay Inn and Conference Center
Interior
Lakefront Bolton Alderbrook Chalet w/ Fire Pit!
3.5 star property
Lakefront Bolton Alderbrook Chalet w/ Fire Pit!
Interior
Adirondack Mountains Cottage Near Gore Mountain!
3.5 star property
Adirondack Mountains Cottage Near Gore Mountain!
Interior
Upstate Escape Near Schroon River & North Creek!
3.0 star property
Upstate Escape Near Schroon River & North Creek!
Interior
Adirondack Park Home ~ 10 Mi to Gore Mountain
3.0 star property
Adirondack Park Home ~ 10 Mi to Gore Mountain
Interior
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
3.0 star property
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
Interior
Bolton Landing Cottage With Deck - Walk to Beach!
3.0 star property
Bolton Landing Cottage With Deck - Walk to Beach!
Interior
Recently Renovated Bolton Abode w/ Fire Pit!
3.5 star property
Recently Renovated Bolton Abode w/ Fire Pit!
Interior
Pet-friendly Bolton Vacation Rental w/ Game Room!
3.0 star property
Pet-friendly Bolton Vacation Rental w/ Game Room!
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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.

Frequently asked questions

Where is the best place to stay in Chestertown?

Located 21.4 mi (34.5 km) from the heart of Chestertown, Six Flags Lodge & Indoor Waterpark is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham Lake George and The Queensbury Hotel. See all available top hotels, or 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 accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Pine Tree Motel & Cabins is a popular 2-star property for our travelers looking for an economical choice, and features free WiFi and free parking. View all budget hotels in Chestertown.

What's the best accommodation for a family vacation in Chestertown?

Pine Tree Motel & Cabins is a property with free parking and free WiFi, and it's a top choice on Expedia for families. The Fern Lodge is another choice for your family trip. Attractions in the area like Garnet Hill Lodge and Ski Resort and House of Frankenstein Wax Museum are also fun for kids of all ages. Find more child-friendly accommodations in Chestertown.

What's the best hotel for couples in Chestertown?

Friends Lake Inn is a favorite 4-star hotel for couples, and features a full-service spa and wedding services. Another choice for a romantic stay is The Fern Lodge. See all romantic hotels in Chestertown.

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. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best place to stay close to Loon Lake Beach?

Pine Tree Motel & Cabins is one of the top choices for your stay based on our traveler data, and this property offers free WiFi and free parking. It's located just a short 0.5 mi (0.8 km) from Loon Lake Beach. Another good choice is Friends Lake Inn, located 1.6 mi (2.6 km) away.

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 spa tubs, and it's located close to Loon Lake Beach. See more stays near the beach in Chestertown.

What's the best luxury place to stay in Chestertown?

Friends Lake Inn is a 4-star hotel with a full-service spa and a terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Chestertown.

What's the best place to stay for a winter vacation in Chestertown?

Based on our travel data, The Fern Lodge is a top 3.5-star B&B for a winter vacation, and features ski passes and private spa tubs. Friends Lake Inn is another good choice for your ski trip. Those looking to ski or snowboard can spend their days at Gore Mountain Ski Resort.

What are some accommodations with pools in Chestertown?

La Quinta Inn & Suites by Wyndham Lake George: Hotel located near Six Flags Great Escape. Offers daily, an indoor pool, and free self parking. The Queensbury Hotel and Country Inn & Suites by Radisson, Lake George (Queensbury), NY are two additional hotels that feature an onsite pool. View all hotels with pools in Chestertown.

What is the best spa hotel in Chestertown?

Friends Lake Inn is a top spa hotel featuring a bar and a restaurant. See all spa hotels in Chestertown.

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 110 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.