Photo by Julie Miller

Find hotels in Chestertown, NY from SAR 195

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Chestertown hotel prices

Filter by

Guest rating
Guest rating
Star rating

Compare 1,476 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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!

Lodge at Schroon Lake

3.0 star property
8.8 out of 10, Excellent, (271)
"Loved absolutely everything! The nature is amazing, lovely staff. Food was delicious in the restaurant. A lot of entertainment, clean pool. Will definitely visit again "
The price is SAR 522
SAR 683 total
includes taxes & fees
5 Jan - 6 January 2025
Lodge at Schroon Lake

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (3)
"It was great, exactly what we needed!"
The price is SAR 543
SAR 696 total
includes taxes & fees
2 Jan - 3 January 2025
Trout House Village Resort

Best Western Plus Ticonderoga Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (668)
"We had a great stay"
The price is SAR 372
SAR 420 total
includes taxes & fees
5 Jan - 6 January 2025
Best Western Plus Ticonderoga Inn & Suites

Super 8 by Wyndham Ticonderoga

2.5 star property
7.8 out of 10, Good, (986)
"Very pleased with the accommodations"
The price is SAR 255
SAR 288 total
includes taxes & fees
1 Jan - 2 January 2025
Super 8 by Wyndham Ticonderoga

Maple Leaf Motel

2.5 star property
8.8 out of 10, Excellent, (408)
"Such a great little treasure nestled in the North Country! Super easy check in, clean and comfortable rooms, a bunch of little surprises in the room to make your stay even more enjoyable. What a fantastic spot! "
The price is SAR 368
SAR 416 total
includes taxes & fees
24 Jan - 25 January 2025
Maple Leaf Motel

Circle Court Motel

2.5 star property
8.8 out of 10, Excellent, (267)
"Simple and clean. This is all we needed."
Circle Court Motel

Chateau Rooms

4.5 star property
9.0 out of 10, Wonderful, (51)
"We had the property to ourselves with the exception of guests of the restaurant. Was a beautiful and relaxing weekend for my wife and I to lay in bed and reconnect."
Chateau Rooms

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (84)
"Great room, very nice staff. Nice weekend getaway."
The price is SAR 838
SAR 930 total
includes taxes & fees
26 Dec - 27 Dec
Friends Lake Inn

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is SAR 2,160
SAR 2,398 total
includes taxes & fees
29 Dec - 30 Dec
The Fern Lodge

Boathouse Waterfront Lodging

3.5 star property
9.4 out of 10, Exceptional, (19)
"The best place to stay, hands down in Bolton and Lake George. I have been many times and cannot wait until next year!!"
Boathouse Waterfront Lodging

Silver Bay YMCA Inn and Conference Center

3.0 star property
8.4 out of 10, Very Good, (84)
"This was a great surprise. What a beautiful place."
The price is SAR 368
SAR 408 total
includes taxes & fees
26 Dec - 27 Dec
Silver Bay YMCA Inn and Conference Center

BEAUTIFUL SECLUDED RUSTIC camp site. Waterfall, creek, swimming hole & trails.

6.8 out of 10, (3)
"We had a wonderful stay. The property was just as advertised and the hosts provided clear instructions and directions about getting there, where to park, accessing the camp site, etc. We stayed on the overlook site, which had a raised wood platform for the tent and was warmer at night for camping in cold temperatures. Was fun to explore the swimming hole and nearby trails."
BEAUTIFUL SECLUDED RUSTIC camp site. Waterfall, creek, swimming hole & trails.

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
Pine Tree Motel & Cabins

Safari Tent nestled in the woods on the Schroon River with beach and island!

4.0 out of 10, (4)
"well, we thought it was going to be glamping. It was worse than camping. It stunk it was dirty. The sheets were never changed. There was dirty dishes. The yard wasn’t mowed. It was just terrible. I would never do this again or recommend anyone to do it."
The price is SAR 428
SAR 770 total
includes taxes & fees
1 Jan - 2 January 2025
Safari Tent nestled in the woods on the Schroon River with beach and island!

Camping Classic ADK style Creekside

8.0 out of 10, Very Good, (1)
"This was a wonderful site that I would love to visit again. The river flowing by was so beautiful. I would like to stay again when we don’t have so much rain. The river was too raging for any swimming. The only downside was there was a bit of a steep walk down to the site from the parking area, but you do have to go downhill to be near a river."
Camping Classic ADK style Creekside

Vintage 4-bedroom house with WiFi in Schroon Lake

2.0 star property
The price is SAR 882
SAR 1,723 total
includes taxes & fees
25 Jan - 26 January 2025
Vintage 4-bedroom house with WiFi in Schroon Lake

Secluded gem with forest view, beach access & W/D

8.0 out of 10, Very Good, (16)
"Overall the online listing is a very accurate representation of the property. It has a very rustic cabin feel. The pond that you can visit is wonderful and well staffed and taken care of. My only complaint is there was no air conditioning in the apartment and it got very hot."
The price is SAR 195
SAR 666 total
includes taxes & fees
31 Dec - 1 January 2025
Secluded gem with forest view, beach access & W/D

Cabin w/ Beach Access in Brant Lake: Dogs Welcome!

3.0 star property
Cabin w/ Beach Access in Brant Lake: Dogs Welcome!

Camp RiverWood on the Hudson River

The price is SAR 507
SAR 687 total
includes taxes & fees
27 Dec - 28 Dec
Camp RiverWood on the Hudson River
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.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in

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 The Queensbury Hotel 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?

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub! : This vacation home rental outside of Chestertown is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 selection of games and a spa tub. 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?

Pine Tree Motel & Cabins is a top pet-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another good option if you're bringing your pet along. See more pet-friendly hotel accommodations 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 spa 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?

The Queensbury Hotel: Offers 2 restaurants, an indoor pool, and 2 bars. La Quinta Inn & Suites by Wyndham Lake George 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'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 116 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.