Photo by Julie Miller

Hotels in Chestertown

Tue, Feb 24
Wed, Feb 25
February 2026
17
March 2026

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Tonight
Feb 17 - Feb 18
Tomorrow
Feb 18 - Feb 19
This weekend
Feb 20 - Feb 22
Next weekend
Feb 27 - Mar 1

Where to stay in Chestertown?

The Fern Lodge
The Fern Lodge
Chestertown
  • Woodland retreat near Adirondack lakes with enchanting private beach and dining.
$507 nightly
$563 total
Feb 22 - Feb 23
Total with taxes and fees
The Fern Lodge
Llama House ADK
Llama House ADK
Wevertown
  • Cozy lodge near Gore Mountain, with free WiFi and hiking trails to explore.
$140 nightly
$156 total
Feb 24 - Feb 25
Total with taxes and fees
Llama House ADK
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Bolton Landing
$1,225 nightly
$1,360 total
Feb 23 - Feb 24
Total with taxes and fees
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
The Alpine Lodge
The Alpine Lodge
North Creek
$188 nightly
$209 total
Mar 3 - Mar 4
Total with taxes and fees
The Alpine Lodge
Gore Mountain Lodge
Gore Mountain Lodge
North Creek
$229 nightly
$254 total
Feb 25 - Feb 26
Total with taxes and fees
Gore Mountain Lodge
North Creek Lodge at Gore Mountain
North Creek Lodge at Gore Mountain
North Creek
  • Slope-side convenience meets mountain charm at this cozy North Creek lodge with free perks.
$205 nightly
$227 total
Feb 18 - Feb 19
Total with taxes and fees
North Creek Lodge at Gore Mountain
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Olmstedville
  • Experience the tranquility of a golf-adjacent home in Olmstedville with hiking trails.
$729 nightly
$824 total
Mar 2 - Mar 3
Total with taxes and fees
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Super 8 by Wyndham Lake George/Warrensburg Area
Super 8 by Wyndham Lake George/Warrensburg Area
Lake George
  • Downtown Lake George getaway with free breakfast and easy access to outdoor fun.
$70 nightly
$77 total
Feb 22 - Feb 23
Total with taxes and fees
Super 8 by Wyndham Lake George/Warrensburg Area
Lodge at Schroon Lake
Lodge at Schroon Lake
Schroon Lake
  • Rustic lakeside retreat with private beach, indoor pool, and marina access.
$174 nightly
$197 total
Feb 18 - Feb 19
Total with taxes and fees
Lodge at Schroon Lake
Maple Leaf Motel
Maple Leaf Motel
Schroon Lake
  • Cozy lakeside motel with a seasonal pool and golf course for outdoor enthusiasts.
$116 nightly
$131 total
Feb 20 - Feb 21
Total with taxes and fees
Maple Leaf Motel
Silver Bay YMCA Inn and Conference Center
Silver Bay YMCA Inn and Conference Center
Silver Bay
  • Lakeside tranquility at this serene YMCA inn with fitness center, dining, and beach.
$104 nightly
$115 total
Feb 18 - Feb 19
Total with taxes and fees
Silver Bay YMCA Inn and Conference Center
Lodges At Cresthaven
Lodges At Cresthaven
Lake George
  • Experience Lake George's charm at this lodge just 15 minutes from Six Flags.
$154 nightly
$171 total
Feb 22 - Feb 23
Total with taxes and fees
Lodges At Cresthaven
Sun Castle Resort
Sun Castle Resort
Lake George
$314 nightly
$340 total
Feb 18 - Feb 19
Total with taxes and fees
Sun Castle Resort
Pinebrook Motel
Pinebrook Motel
Lake George
  • Close to Lake George and Six Flags, enjoy a refreshing pool after adventure.
$57 nightly
$63 total
Mar 8 - Mar 9
Total with taxes and fees
Pinebrook Motel
Sundowner on Lake George
Sundowner on Lake George
Lake George
  • Relax at this lakeside motel with a seasonal pool and private beach access.
$156 nightly
$173 total
Mar 2 - Mar 3
Total with taxes and fees
Sundowner on Lake George
Lake Haven Motel
Lake Haven Motel
Lake George
  • Stay lakeside at this relaxing motel, minutes from Six Flags Great Escape.
$218 nightly
$242 total
Feb 19 - Feb 20
Total with taxes and fees
Lake Haven Motel
Courtyard by Marriott Lake George
Courtyard by Marriott Lake George
Lake George
  • Relax by Lake George with an indoor pool, on-site dining, and convenient amenities.
$112 nightly
$124 total
Feb 22 - Feb 23
Total with taxes and fees
Courtyard by Marriott Lake George
The Inn of Lake George
The Inn of Lake George
Lake George
  • Unwind just minutes from Lake George with premium bedding and attentive service.
$112 nightly
$124 total
Feb 18 - Feb 19
Total with taxes and fees
The Inn of Lake George
Surfside On The Lake
Surfside On The Lake
Lake George
  • Walk steps from pristine waters to a welcoming lakefront escape with a rooftop bar.
$237 nightly
$263 total
Mar 1 - Mar 2
Total with taxes and fees
Surfside On The Lake
Howard Johnson by Wyndham Lake George
Howard Johnson by Wyndham Lake George
Lake George
  • Central to Lake George attractions with a relaxing pool to complete your day.
$79 nightly
$88 total
Feb 18 - Feb 19
Total with taxes and fees
Howard Johnson by Wyndham Lake George
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Our prices for hotels in Chestertown are cheapest in October
Price trends for hotels in Chestertown
Pricing is based on two traveler single night rates
View properties in February
Typical weather for Chestertown
February
High 30°F / low 14°F. Snow likely.
View properties in February
30°
14°
39°
22°
52°
33°
67°
45°
74°
53°
80°
59°
78°
58°
71°
51°
57°
41°
44°
29°
33°
22°
28°
13°
Monthly weather averages (˚F)

Top neighborhoods in Chestertown

Chester Shores

Chestertown's Chester Shores neighborhood offers attractions including Loon Lake.

Top landmarks in Chestertown

Loon Lake

Crystal waters of Loon Lake reflect the Adirondack Mountains, creating a paddler's paradise in upstate New York. Bring your own picnic and rent a kayak to spot the lake's namesake birds calling across the water.
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Friends Lake

This private Adirondack lake offers pristine waters and tranquil surroundings for swimming, fishing, and kayaking. Access is limited to guests of lakeside accommodations, ensuring a peaceful retreat from crowds.
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Loon Lake Beach

Loon Lake Beach offers pristine Adirondack swimming with a sandy shoreline perfect for summer relaxation. Arrive with picnic supplies in hand as concessions are limited at this peaceful mountain retreat.
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Tripp Pond

Tripp Pond offers serene waters perfect for fishing and kayaking amid lush forests. Bring your own gear to this peaceful retreat where morning visits reward you with active wildlife and stunning photo ops.
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Learn more about Chestertown

Chestertown is well-known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.

See all hotels in Chestertown
A winter scene
Photo by Julie Miller

Check out reviews of Chestertown hotels guests love

Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"This was our very favorite family two night getaway. All of the staff, in the hotel, restaurant and indoor water park were very nice and helpful! We had a suite, which made it easy to eat breakfast in the room, hit the park for a bit, then change up and go see other attractions in and around Lake George. I was thoroughly impressed by the attention to cleanliness and due diligence of the indoor water park. While we were there we saw them running a drill and they had to quickly remove guests from the lazy river after a boy had cut his arm. Things happen, so it was good to know that they handled incidents quickly and correctly. "
Ashley 2-night trip
Posted 1 day ago
Six Flags Great Escape Lodge & Indoor Waterpark
The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Was great experience "
Valery 1-night trip
Posted 1 day ago
The Queensbury Hotel
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Very clean and it had very comfortable beds. Also on site access to restaurant and nearby access to downtown. "
Taylor 2-night trip
Posted 1 day ago
Fort William Henry Hotel and Conference Center
Best Western of Lake George

Best Western of Lake George

10/10 Excellent
"The room was spotless.. big shower/ water pressure great/ plenty of pillows on the huge king bed I had to myself. The gal at check in( didn't catch name but she was rocking purple hair/ and she drives a jeep) was super nice and helpful.. I didn't go through lobby again..used other door to go in and out.. and left key cards/ tip in room.. the only one complaint I had (no ones fault is that wifi service was terrible/ signal on then lost constantly) I didnt use other amenities or have breakfast there but all good."
Kristin 2-night trip
Posted 2 days ago
Best Western of Lake George
Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area

10/10 Excellent
"It's a basic hotel but rooms are clean, comfortable and nice. It's great value for money!"
Stefano 1-night trip
Posted 5 days ago
Super 8 by Wyndham Lake George/Warrensburg Area
Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George

10/10 Excellent
"Everything stood out! This was honestly a very wonderful hotel experience for us, and we stay at a lot of hotels throughout the year. Highlights: Our room was spotless. The staff was incredibly nice. The breakfast offered a lot of variety. Our family really enjoyed the pool and hot tub as well."
Samantha 2-night trip
Posted 6 days ago
Hampton Inn & Suites Lake George
Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"The room was clean and the heat work great. Since we were there for the winter carnival it was nice to walk into a warm room"
Pamela 1-night trip
Posted 8 days ago
Howard Johnson by Wyndham Lake George
Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

10/10 Excellent
"Room was great, staff is great, second time at this hotel and it was consistent with the first stay!! Highly recommend"
Sandy 2-night trip
Posted 10 days ago
Courtyard by Marriott Lake George
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"Great staff and fun place for the kids. "
Robert 1-night trip
Posted 11 days ago
La Quinta Inn & Suites by Wyndham Lake George

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from $63 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".
How can I find deals and earn rewards at Chestertown hotels?
Discover great deals on Chestertown hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. And make sure to check out our last-minute deals on Chestertown hotels.
Can I book Chestertown hotels with free cancellation?
In order to book a refundable Chestertown hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best hotels in Chestertown for couples?
Stay at a top-rated Chestertown romantic hotel and make the most of your couple's vacation. Our travelers love Friends Lake Inn, a hotel with a restaurant as well as in-room champagne service. Another romantic hotel with top reviews is The Fern Lodge. This bed & breakfast offers a private hot tub and an in-room fireplace for a perfect stay. Discover more hotels in Chestertown on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".
What are some of the best Chestertown hotels with free parking?
If you're driving, a great Chestertown hotel with free parking is a bonus. Our travelers' favorites include:
What are some popular hotels in central Chestertown?
If you're looking for hotels in central Chestertown, check out Friends Lake Inn. Travelers love Friends Lake Inn for its location, as well as the restaurant, bar/lounge and couples/private dining this hotel offers. Chester Shores is a central neighborhood for your Chestertown vacation.
What accommodations do travelers like in Chestertown?
Can I book a refundable accommodation in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chestertown if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, look over our selection of 59 vacation homes. You can also consider one of the 6 apartments or 19 cottages.
What will the weather in Chestertown be like during my visit?
The warmest months in Chestertown are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 25°F. The rainiest months are June and July.
Why should I book my Chestertown hotel with Hotels.com?
There are plenty of reasons to book your Chestertown travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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