Photo by Julie Miller

Chestertown Hotels from S$96

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Top 10 trending Chestertown hotels

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, (270)
"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 S$262
includes taxes & fees
23 Dec - 24 Dec
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 S$251
includes taxes & fees
23 Dec - 24 Dec
Trout House Village Resort

Best Western Plus Ticonderoga Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (666)
"We had a great stay"
The price is S$152
includes taxes & fees
5 Jan - 6 Jan,2025
Best Western Plus Ticonderoga Inn & Suites

Super 8 by Wyndham Ticonderoga

2.5 star property
7.8 out of 10, Good, (984)
"Very pleased with the accommodations"
The price is S$104
includes taxes & fees
29 Dec - 30 Dec
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 S$150
includes taxes & fees
5 Jan - 6 Jan,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

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

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 S$353
includes taxes & fees
24 Dec - 25 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 S$901
includes taxes & fees
28 Dec - 29 Dec
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 S$148
includes taxes & fees
26 Dec - 27 Dec
Silver Bay YMCA Inn and Conference Center

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

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

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

Tree Tops Retreat ~ 19 Mi to Lake George!

3.0 star property
Tree Tops Retreat ~ 19 Mi to Lake George!

Peaceful Brant Lake Home < 1 Mi to Beach!

3.0 star property
10.0 out of 10, Exceptional, (3)
"House is amazing and roomy"
Peaceful Brant Lake Home < 1 Mi to Beach!

Updated Bolton Home w/ Fire Pit!

3.0 star property
Updated Bolton Home w/ Fire Pit!

Pet-friendly Bolton Vacation Rental w/ Game Room!

3.0 star property
Pet-friendly Bolton Vacation Rental w/ Game Room!

Family Gem: Private Community Beach on Tripp Lake

3.0 star property
Family Gem: Private Community Beach on Tripp Lake

Chestertown Hideaway w/ Lake & Beach Access!

3.0 star property
Chestertown Hideaway w/ Lake & Beach Access!
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.
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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 traveller data. Other good choices for your stay in the area are The Queensbury Hotel and Holiday Inn Resort Lake George - Adirondack Area, an IHG 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 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. 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?

The Queensbury Hotel: Offers 2 restaurants, an indoor pool and 2 bars. Holiday Inn Resort Lake George - Adirondack Area, an IHG 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 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.