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Hotels in Chestertown

October 2026
18
November 2026

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Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Where to stay in Chestertown?

Room
Room
Television
Room

1. Friends Lake Inn

Friends Lake Inn
Chestertown
$115
$127 total
includes taxes & fees
Nov 2 - Nov 3
Friends Lake Inn
A cozy log cabin interior with a stone fireplace, wooden ceiling, and a large arched window.
A stone fireplace with a wooden mantel, surrounded by a wooden gazebo with a triangular roof, and a stone pathway leading to it.
A kitchen with wooden cabinets, stainless steel appliances, granite countertops, and pendant lighting.
A two-story building with a dark exterior, a covered front porch, and a sign reading "TALPINE LODGE".

2. The Alpine Lodge

The Alpine Lodge
North Creek
$140
$167 total
includes taxes & fees
Oct 27 - Oct 28
The Alpine Lodge
A log cabin-style building with a porch, windows, and a green roof.
A room with two beds, wooden walls, a window, a desk with a computer, and a lamp.
A room with a wooden bench, a table, and chairs. There is a map on the wall and a window with a curtain.
A wooden cabin with a picnic table and a barbecue grill.

3. Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
Lake George
$71
$79 total
includes taxes & fees
Nov 8 - Nov 9
Super 8 by Wyndham Lake George/Warrensburg Area
A row of cabins with balconies, a well-maintained lawn, and a lake view.
A log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.
A dining area with a table set for four, large windows offering a view of a lake and trees, and a stone wall in the background.
A lakeside property with docked boats, a stone pathway, and a view of the surrounding forest and buildings.

4. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
$137
$188 total
includes taxes & fees
Nov 8 - Nov 9
Lodge at Schroon Lake
A wooden lodge with a metal roof, a covered porch, and a sign that reads "Becks."
A rustic interior with wooden beams, a large window, and multiple tables and chairs.
A bar area with wooden windows, shelves of liquor bottles, and glasses.
A lodge sign with a mountain graphic, surrounded by greenery and two yellow chairs.

5. Gore Mountain Lodge

Gore Mountain Lodge
North Creek
$149
$165 total
includes taxes & fees
Oct 21 - Oct 22
Gore Mountain Lodge
A cozy room with a fireplace, wooden furniture, and a framed picture of the Adirondack High Peaks.
A room with a wooden dresser, a desk with a chair, a television, a lamp, and a window with curtains.
A hotel room with a bed, a wooden dresser with drawers, a television on top, a desk with a chair, and a mirror on the wall.
A snow-covered cabin with a wooden exterior and a single visible door.

6. North Creek Lodge at Gore Mountain

North Creek Lodge at Gore Mountain
North Creek
$101
$112 total
includes taxes & fees
Oct 20 - Oct 21
North Creek Lodge at Gore Mountain
A patio area with a stone fire pit, wooden chairs, and tables, surrounded by a building with large windows and a stone facade.
An indoor swimming pool with a brick floor, lounge chairs, and a stone wall.
A hotel lobby with a reception desk, seating area, stone fireplace, and large windows.
A spacious living area with a stone fireplace, comfortable seating, a large window with a view, and a chandelier.

7. Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG
Lake George
$112
$124 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn Resort Lake George - Adirondack Area by IHG
A large, historic hotel with multiple buildings, a well-maintained lawn, and a mountainous backdrop.
A room with a view of a lake and autumn foliage through large windows.
A conference room with large windows offering a view of a mountainous landscape.
A spacious room with a stone fireplace, wooden beams, and a herringbone-patterned floor.

8. Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center
Silver Bay
$91
$101 total
includes taxes & fees
Oct 25 - Oct 26
Silver Bay YMCA Inn and Conference Center
Room
A couple sitting on a green sofa in a hotel lobby with a tiled floor and wooden shelves in the background.
A hotel room with two beds, a desk, a chair, a large window with a view of a lake and hills, and a carpeted floor.
A bar area with wooden chairs, a counter with a glass display, and hanging lights.

9. Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
Lake George
$124
$138 total
includes taxes & fees
Nov 2 - Nov 3
Courtyard by Marriott Lake George
A hotel entrance with a stone facade, a covered entrance area, and a landscaped driveway.
A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.
A Comfort Inn & Suites sign with a blue background and a yellow stripe.
A spacious lobby with a high ceiling, a staircase, and a reception desk.

10. Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George
Lake George
$101
$112 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Lake George
A pool area with a yellow water slide and a pool.
A hotel with a prominent 'LAQUINTA' sign, a covered entrance, and a parking lot.
A hotel room with a large bathtub, a bed with white bedding, a dark headboard, and a black and white patterned floor.
A spacious lobby with a curved staircase, a reception desk, and a decorative wall.

11. La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
Lake George
$84
$93 total
includes taxes & fees
Oct 28 - Oct 29
La Quinta Inn & Suites by Wyndham Lake George
An outdoor patio with red Adirondack chairs, a wooden pergola, and a covered seating area with picnic tables.
Breakfast area
A spacious lobby with a reception desk, seating area, staircase, and fireplace.
A hotel room with a kitchenette, a bed, a desk, a chair, and a large mirror.

12. Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Queensbury
$79
$88 total
includes taxes & fees
Nov 8 - Nov 9
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
A hotel room with two beds, a desk with a television, and a window with curtains.
A hotel pool area with multiple pools, lounge chairs, and a covered seating area.
A hotel room with a television, sofa, armchair, dining table, and chairs.
A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a coffee maker on the countertop.

13. Skyline Hotel Lake George

Skyline Hotel Lake George
Lake George
$72
$80 total
includes taxes & fees
Oct 25 - Oct 26
Skyline Hotel Lake George
A kitchen with dark wooden cabinets, a granite countertop, a stainless steel sink, and a built-in coffee maker.
A dining area with a round table, four chairs, and a window with blinds.
A two-story white building with a porch, labeled "Maple Leaf Lodge".
A living room with a grey sectional sofa, a round mirror, a lamp, and a patterned rug.

14. Maple Leaf Motel

Maple Leaf Motel
Schroon Lake
$129
$146 total
includes taxes & fees
Oct 19 - Oct 20
Maple Leaf Motel
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
Dining
A hotel room with a bed, a sofa, a small table, and a chair.
A modern restaurant with a central bar, dining area with tables and chairs, and large windows with arched tops.

15. Public House

Public House
North Creek
$152
$169 total
includes taxes & fees
Oct 25 - Oct 26
Public House
A poolside area with lounge chairs and umbrellas, a bar, and a view of the sea and mountains at night.
A restaurant with tables and chairs, large windows with a view of a beach and mountains, and a carpeted floor.
A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.
A marina with docked boats, a covered seating area, and a view of a lake with mountains in the background.

16. The Georgian Lakeside Resort

The Georgian Lakeside Resort
Lake George
$109
$121 total
includes taxes & fees
Oct 19 - Oct 20
The Georgian Lakeside Resort
An outdoor patio with a fire pit, dining tables, chairs, and umbrellas.
A spacious lobby with a stone fireplace, blue seating, and a large chandelier.
A spacious dining area with a high ceiling, large windows, and a mix of seating arrangements including a bench and individual chairs.
A spa area with a hot tub, seating, and a view of the outdoors.

17. Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George
Lake George
$103
$114 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn & Suites Lake George
An outdoor patio with a wooden pergola, stone walls, and a fire feature.
A cozy living room with a fireplace, comfortable seating, and a large window.
A rectangular swimming pool with a metal ladder, surrounded by a fence and outdoor seating.
A rustic bar area with a wooden counter, coffee machines, and a variety of coffee cups and mugs.

18. Super 8 by Wyndham Lake George/Downtown

Super 8 by Wyndham Lake George/Downtown
Lake George
$69
$79 total
includes taxes & fees
Oct 25 - Oct 26
Super 8 by Wyndham Lake George/Downtown
A lobby with a TV displaying a programming schedule, a reception desk, and seating areas with yellow chairs and a sofa.
A modern building with a parking lot, landscaped areas with flowers, and a clear sky.
A restaurant with a coffee station, seating area, and a TV mounted on the wall.
A spacious living area with a sofa, coffee table, and a chandelier. There are potted plants and a magazine rack.

19. Wingate by Wyndham Lake George

Wingate by Wyndham Lake George
Lake George
$79
$88 total
includes taxes & fees
Oct 19 - Oct 20
Wingate by Wyndham Lake George
An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.
A wooden cabin interior with a kitchen featuring a stainless steel refrigerator, wooden cabinets, and a bar area with stools.
A snow-covered lodge with cabins, a clear view of a lake, and mountains in the background.
A lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.

20. Lodges At Cresthaven

Lodges At Cresthaven
Lake George
$181
$201 total
includes taxes & fees
Nov 8 - Nov 9
Lodges At Cresthaven
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Go beyond your typical stay in Chestertown

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Our prices for hotels in Chestertown are cheapest in September

Price trends for hotels in Chestertown

Pricing is based on two traveler single night rates
View properties in October

October

High 14°C / low 5°C. Cloudy most days.
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Monthly weather averages (˚C)

Top neighborhoods in Chestertown

Chester Shores

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

Top landmarks in Chestertown

Loon Lake

8.8/10 (8 reviews)
Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay.
See properties

Friends Lake

9.4/10 (14 reviews)
Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay.
See properties

Loon Lake Beach

8.4/10 (7 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Loon Lake Beach located 2 mi (3.3 km) from central Chestertown.
See properties

Tripp Pond

8.6/10 (4 reviews)
Tripp Pond is 3.9 mi (6.3 km) from central Chestertown, why not stop by during your stay.
See properties

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 waterfront town with a pier, dock, and several buildings.

Check out reviews of Chestertown hotels guests love

A patio area with a stone fire pit, wooden chairs, and tables, surrounded by a building with large windows and a stone facade.
An indoor swimming pool with a brick floor, lounge chairs, and a stone wall.
A hotel lobby with a reception desk, seating area, stone fireplace, and large windows.
A spacious living area with a stone fireplace, comfortable seating, a large window with a view, and a chandelier.

Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG
Lake George

10/10 Exceptional

United States
Thomas
Holiday Inn Resort Lake George - Adirondack Area by IHG
An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.
A wooden cabin interior with a kitchen featuring a stainless steel refrigerator, wooden cabinets, and a bar area with stools.
A snow-covered lodge with cabins, a clear view of a lake, and mountains in the background.
A lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.

Lodges At Cresthaven

Lodges At Cresthaven
Lake George

10/10 Exceptional

United States
Sheila
Lodges At Cresthaven
Room
A couple sitting on a green sofa in a hotel lobby with a tiled floor and wooden shelves in the background.
A hotel room with two beds, a desk, a chair, a large window with a view of a lake and hills, and a carpeted floor.
A bar area with wooden chairs, a counter with a glass display, and hanging lights.

Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
Lake George

10/10 Exceptional

United States
Anonymous traveler
Courtyard by Marriott Lake George
A cozy log cabin interior with a stone fireplace, wooden ceiling, and a large arched window.
A stone fireplace with a wooden mantel, surrounded by a wooden gazebo with a triangular roof, and a stone pathway leading to it.
A kitchen with wooden cabinets, stainless steel appliances, granite countertops, and pendant lighting.
A two-story building with a dark exterior, a covered front porch, and a sign reading "TALPINE LODGE".

The Alpine Lodge

The Alpine Lodge
North Creek

10/10 Exceptional

United States
Kim
The Alpine Lodge
A hotel entrance with a stone facade, a covered entrance area, and a landscaped driveway.
A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.
A Comfort Inn & Suites sign with a blue background and a yellow stripe.
A spacious lobby with a high ceiling, a staircase, and a reception desk.

Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George
Lake George

10/10 Exceptional

United States
Steven
Comfort Inn & Suites Lake George
A spacious living area with a sofa, a chandelier, and a clock on the wall.
A two-story building with a pool, white railings, and a garden with rocks and flowers.
A patio area with a stone fire pit, white outdoor furniture, and a white picket fence.
A spacious kitchen with a central island, a chandelier, and a ceiling fan.

Quality Inn Lake George

Quality Inn Lake George
Lake George

10/10 Exceptional

United States
tourists
Quality Inn Lake George
A row of cabins with balconies, a well-maintained lawn, and a lake view.
A log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.
A dining area with a table set for four, large windows offering a view of a lake and trees, and a stone wall in the background.
A lakeside property with docked boats, a stone pathway, and a view of the surrounding forest and buildings.

Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake

10/10 Exceptional

United States
Connie
Lodge at Schroon Lake
An outdoor patio with a fire pit, dining tables, chairs, and umbrellas.
A spacious lobby with a stone fireplace, blue seating, and a large chandelier.
A spacious dining area with a high ceiling, large windows, and a mix of seating arrangements including a bench and individual chairs.
A spa area with a hot tub, seating, and a view of the outdoors.

Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George
Lake George

10/10 Exceptional

United States
Glenn
Hampton Inn & Suites Lake George
A modern hotel entrance with a covered waiting area, stone pillars, and a blue-lit facade.
A modern hotel lobby with a seating area, a bar, and a kitchen in the background.
An outdoor patio with tables and chairs, large windows, and a stone wall.
A hotel reception area with a modern design, featuring a reception desk, a digital screen, and a wooden floor.

Holiday Inn Express Queensbury - Lake George Area by IHG

Holiday Inn Express Queensbury - Lake George Area by IHG
Queensbury

10/10 Exceptional

United States
Anonymous traveler
Holiday Inn Express Queensbury - Lake George Area by IHG
A modern kitchen with a built-in microwave, coffee maker, and dishwasher.
A multi-story hotel with a modern design, featuring a prominent 'HOME 2' sign on the facade.
A hotel room with two beds, a sofa, a colorful ottoman, a painting on the wall, and a large window.
A modern kitchen with a refrigerator, microwave, and dishwasher, a flat-screen TV, a desk with a chair, and a patterned carpet.

Home2 Suites by Hilton Queensbury Lake George

Home2 Suites by Hilton Queensbury Lake George
Queensbury

10/10 Exceptional

United States
Nicole
Home2 Suites by Hilton Queensbury Lake George
A wooden lodge with a metal roof, a covered porch, and a sign that reads "Becks."
A rustic interior with wooden beams, a large window, and multiple tables and chairs.
A bar area with wooden windows, shelves of liquor bottles, and glasses.
A lodge sign with a mountain graphic, surrounded by greenery and two yellow chairs.

Gore Mountain Lodge

Gore Mountain Lodge
North Creek

10/10 Exceptional

United States
Anonymous traveler
Gore Mountain Lodge
A pool area with a yellow water slide and a pool.
A hotel with a prominent 'LAQUINTA' sign, a covered entrance, and a parking lot.
A hotel room with a large bathtub, a bed with white bedding, a dark headboard, and a black and white patterned floor.
A spacious lobby with a curved staircase, a reception desk, and a decorative wall.

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
Lake George

10/10 Exceptional

United States
Brian
La Quinta Inn & Suites by Wyndham Lake George
A bar area with wooden bar stools, a bar counter, and a ceiling with intricate designs.
A bar area with leather chairs, a wooden counter, and decorative lighting.
A neatly made bed with white linens and pillows, a grey upholstered headboard, and a wooden nightstand with a white lamp.
A cozy corner with a blue cushioned bench, green upholstered chairs, and a wooden table.

The Inn of Lake George

The Inn of Lake George
Lake George

10/10 Exceptional

United States
Helmut
The Inn of Lake George
A log cabin-style building with a porch, windows, and a green roof.
A room with two beds, wooden walls, a window, a desk with a computer, and a lamp.
A room with a wooden bench, a table, and chairs. There is a map on the wall and a window with a curtain.
A wooden cabin with a picnic table and a barbecue grill.

Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
Lake George

10/10 Exceptional

United States
Michelle
Super 8 by Wyndham Lake George/Warrensburg Area
A lakeside cabin with a wooden deck and a view of the lake.
A waterfront property with docked boats, a wooden fence, and a sign reading "Grout House."
A log cabin with a balcony and a stone foundation.
A cozy cabin interior with a stone fireplace, wooden furniture, a kitchen area, and a balcony.

Trout House Village Resort

Trout House Village Resort
Hague

10/10 Exceptional

United States
Ann
Trout House Village Resort

Frequently Asked Questions

What accommodations do travelers like in Chestertown?

Guests like Pine Tree Motel & Cabins.

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 62 vacation homes. You can also consider one of the 5 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.