Photo by Julie Miller

Search Chestertown hotels

    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

Tomorrow night
This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Chestertown

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, (262)
"Everyone on the staff is helpful and friendly. The property is conveniently located and easy to find. It's not your typical hotel but well worth checking out. Kid and dog friendly too!"
The price is AU$219
includes taxes & fees
27 Nov - 28 Nov
Lodge at Schroon Lake
Super 8 by Wyndham Ticonderoga
2.5 star property
7.8 out of 10, Good, (984)
"Very pleased with the accommodations"
The price is AU$133
includes taxes & fees
2 Dec - 3 Dec
Super 8 by Wyndham Ticonderoga
Best Western Plus Ticonderoga Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (662)
"Enjoyed our stay but the breakfast food that was to be hot -was cold! "
The price is AU$207
includes taxes & fees
25 Nov - 26 Nov
Best Western Plus Ticonderoga Inn & Suites
Circle Court Motel
2.5 star property
8.6 out of 10, Excellent, (265)
"It was exactly as expected"
Circle Court Motel
Trout House Village Resort
3.0 star property
10.0 out of 10, Exceptional, (1)
"This one checked all the boxes. The location was great. The cabin was clean, spacious, and nicely decorated in Adirondack style. There were many activities available on the grounds at no extra charge. They even had the fireplace in front of our cabin stacked and ready to light. "
The price is AU$282
includes taxes & fees
22 Nov - 23 Nov
Trout House Village Resort
Maple Leaf Motel
2.5 star property
8.6 out of 10, Excellent, (404)
"The stay, for the most part was comfortable. As previously mentioned, we could have used a second chair. Housekeeping did not leave any coffee for the second day and the coffee cups were not cleaned. I know budgets are tight but it would have nice to have had plastic cups, tissues and paper towels incase of spills"
The price is AU$169
includes taxes & fees
6 Dec - 7 Dec
Maple Leaf Motel
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
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
Chateau Rooms
4.5 star property
9.0 out of 10, Wonderful, (49)
"Cozy, private and quiet was just what we needed. Warm and comfortable bed. Close to boat rental and hiking. "
Chateau Rooms
Friends Lake Inn
4.0 star property
8.8 out of 10, Excellent, (83)
"Great room, very nice staff. Nice weekend getaway."
The price is AU$259
includes taxes & fees
22 Nov - 23 Nov
Friends Lake Inn
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."
The price is AU$94
includes taxes & fees
25 Nov - 26 Nov
BEAUTIFUL SECLUDED RUSTIC camp site. Waterfall, creek, swimming hole & trails.
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 AU$790
includes taxes & fees
25 Nov - 26 Nov
The Fern Lodge
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 AU$167
includes taxes & fees
22 Nov - 23 Nov
Silver Bay YMCA Inn and Conference Center
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 AU$317
includes taxes & fees
28 Nov - 29 Nov
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."
The price is AU$100
includes taxes & fees
22 Nov - 23 Nov
Camping Classic ADK style Creekside
WATERFRONT and AFFORDABLE
8.2 out of 10, Very good, (27)
"Absolutely 10 stars. Private✔️Pet friendly✔️View ✔️ Remember, It's camping at its finest. Clean, comfortable and enough room for larger family's Highly recommend. Will be returning "
WATERFRONT and AFFORDABLE
Cabin w/ Beach Access in Brant Lake: Dogs Welcome!
3.0 star property
Cabin w/ Beach Access in Brant Lake: Dogs Welcome!
Reno done! Bolton Blue, Walk to Beach
2.0 star property
10.0 out of 10, Exceptional, (3)
"We are long-time summer residents who needed alternative housing. We are so glad that we were able to rent this home. You walk in the door, and just wow. The view is 180 degrees of mountains, lake, and clouds. You can just enjoy the view all day. Everything was well stocked and comfortable. Beds were great. The dining room-kitchen area made for easy cooking and dining. Wonderful deck for watching sunsets. This is a perfect place for family time, and everyone had plenty of privacy. It's a retreat...
Reno done! Bolton Blue, Walk to Beach
Secluded gem with forest view, beach access & W/D
7.8 out of 10, Good, (15)
"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."
Secluded gem with forest view, beach access & W/D
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
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Where is the best place to stay in Chestertown?

Friends Lake Inn is a favourite with Expedia customers. This hotel offers a restaurant and free parking. Another top choice for your visit based on reviews is Pine Tree Motel & Cabins. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub! : This holiday home rental outside of Chestertown is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot 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 most room reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

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 travellers looking for an economical choice, and features free WiFi and free parking. View all budget hotels in Chestertown.

What's the best place to stay for a family holiday 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 good option for your child-friendly holiday. Also, attractions in the area such as Garnet Hill Lodge and Ski Resort and House of Frankenstein Wax Museum are fun for children of all ages. Find more child-friendly accommodations in Chestertown.

What's the best hotel for a couple visiting Chestertown?

Friends Lake Inn is a favourite 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 hotel 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 dog-friendly place to stay in Chestertown?

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

What's the best hotel for a beach holiday 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's the best luxury accommodation option 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 travellers looking for an elegant place to stay. Find more luxury hotels in Chestertown.

What's the best accommodation option for a trip to the slopes in Chestertown?

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

What are some accommodation options with pools in Chestertown?

Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel: Hotel, 8-minute walk from Fort William Henry. Features a children's pool, an indoor pool and a sauna. The Queensbury Hotel and La Quinta Inn & Suites by Wyndham Lake George are two additional hotels that offer an on-site 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 top hotel in Chestertown with an on-site water park or a water park nearby?

1970s acreage surrounded by trees with deck, grill, & internet is a favourite water park hotel in Chestertown

What is staying in Chestertown like?

Visitors to Chestertown will definitely enjoy the lakeside setting. Tourists can also enjoy the city's coffee shops, forests and seafood restaurants. In Chestertown, there are 115 hotels and other accommodation options to choose from. Find out more about Chestertown.

What is there to see 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 itinerary are Hudson River and Tripp Pond. Take a look at what more there is to see and do in Expedia's Chestertown guide.

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.