𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chestertown (2026)

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

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Our top choices for Chestertown hotels

1. Friends Lake Inn

Chestertown

Pierre

S$142

includes taxes & fees

2 Nov - 3 Nov

A cozy log cabin interior with a stone fireplace, wooden ceiling, and a large arched window.

A kitchen with wooden cabinets, stainless steel appliances, granite countertops, and pendant lighting.

A stone fireplace with a wooden mantel, surrounded by a wooden gazebo with a triangular roof, and a stone pathway leading to it.

A wooden-framed bed with a plaid blanket, a headboard with antlers, and a mounted picture.

2. The Alpine Lodge

North Creek

Patricia

S$193

includes taxes & fees

29 Oct - 30 Oct

A modern lounge area with a round table, chairs, a fireplace, and a television mounted on a textured wall.

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.

3. Courtyard by Marriott Lake George

Lake George

Bob

S$158

includes taxes & fees

2 Nov - 3 Nov

A pool area with a yellow water slide and a pool.

A spacious lobby with a curved staircase, a reception desk, and a decorative wall.

A spacious lobby with a Christmas tree, seating area, and a spiral staircase.

A hotel room with a large bathtub, a bed with white bedding, a dark headboard, and a black and white patterned floor.

4. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Debra

S$119

includes taxes & fees

28 Oct - 29 Oct

A row of cabins with balconies, a well-maintained lawn, and a lake view.

A bar area with a central island, wooden chairs, and a stone fireplace.

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 log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.

5. Lodge at Schroon Lake

Schroon Lake

Marco

S$213

includes taxes & fees

27 Oct - 28 Oct

A log cabin-style building with a porch, windows, and a green roof.

A wooden cabin with a picnic table and a barbecue grill.

A room with a wooden bench, a table, and chairs. There is a map on the wall and a window with a curtain.

A room with a wooden dining table and chairs, a window with lace curtains, and a radiator.

6. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

Augustine

S$92

includes taxes & fees

8 Nov - 9 Nov

A hotel entrance with a stone facade, a covered entrance area, and a landscaped driveway.

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.

A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.

7. Comfort Inn & Suites Lake George

Lake George

Artyom

S$139

includes taxes & fees

24 Nov - 25 Nov

A cozy room with a fireplace, wooden furniture, and a framed picture of the Adirondack High Peaks.

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 white car parked in a lot with other vehicles, trees, and a sunset in the background.

A snow-covered cabin with a wooden exterior and a single visible door.

8. North Creek Lodge at Gore Mountain

North Creek

MICHAEL

S$144

includes taxes & fees

27 Oct - 28 Oct

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 with a covered entrance, large windows, and a parking lot.

A spacious living area with a stone fireplace, comfortable seating, a large window with a view, and a chandelier.

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

Lake George

HAGOP

S$157

includes taxes & fees

15 Nov - 16 Nov

An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.

A lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.

A terrace with outdoor seating, a view of a lake, and a dock.

A wooden cabin interior with a kitchen featuring a stainless steel refrigerator, wooden cabinets, and a bar area with stools.

10. Lodges At Cresthaven

Lake George

christopher

S$211

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with red Adirondack chairs, a wooden pergola, and a covered seating area with picnic tables.

A hotel room with a kitchenette, a bed, a desk, a chair, and a large mirror.

A spacious lobby with a reception desk, seating area, staircase, and fireplace.

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

Queensbury

Nicole

S$111

includes taxes & fees

15 Nov - 16 Nov

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 lifeguard tower with a ladder and a bag of life-saving equipment.

A conference room with large windows offering a view of a mountainous landscape.

12. Silver Bay YMCA Inn and Conference Center

Silver Bay

Scott

S$121

includes taxes & fees

26 Nov - 27 Nov

An outdoor patio with a fire pit, dining tables, chairs, and umbrellas.

A spa area with a hot tub, seating, and a view of the outdoors.

A spacious dining area with a high ceiling, large windows, and a mix of seating arrangements including a bench and individual chairs.

A modern bar area with a white countertop, multiple stools, and a variety of bottles and glasses.

13. Hampton Inn & Suites Lake George

Lake George

PATRICIA

S$146

includes taxes & fees

2 Nov - 3 Nov

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 yurt interior with a central wood-burning stove, leather seating, and a traditional rug.

A lodge sign with a mountain graphic, surrounded by greenery and two yellow chairs.

14. Gore Mountain Lodge

North Creek

Jennifer

S$190

includes taxes & fees

27 Oct - 28 Oct

A spacious living area with a sofa, a chandelier, and a clock on the wall.

A hotel with a swimming pool, multiple lounge chairs, and a white fence surrounding the area.

A two-story building with a pool, white railings, and a garden with rocks and flowers.

A spacious kitchen with a central island, a chandelier, and a ceiling fan.

15. Quality Inn Lake George

Lake George

Laura

S$175

includes taxes & fees

29 Oct - 30 Oct

A dining area with multiple tables and chairs, a kitchen counter, and a television mounted on the wall.

An indoor swimming pool with a hot tub, seating area, and a door with an emergency exit sign.

A lobby with a fireplace, seating area, and a television mounted on the wall.

A hotel with a swimming pool, parking lot, and a view of a lake and mountains.

16. Skyline Hotel Lake George

Lake George

Claudio

S$103

includes taxes & fees

1 Nov - 2 Nov

An outdoor dining area with a fire feature, surrounded by white furniture and a gazebo.

A river with a large white boat docked at a pier, surrounded by autumn-colored trees and buildings in the background.

A dining area with multiple tables and chairs, chandeliers, and large windows with a view of a lake.

A hotel with multiple floors, a parking lot, and a view of a body of water.

17. Fort William Henry Hotel and Conference Center

Lake George

IMTIAZ

S$163

includes taxes & fees

29 Oct - 30 Oct

A hotel room with two beds, a desk, a chair, a TV, and a wall with decorative mirrors.

A two-story building with a sign reading "Howard Johnson."

A coffee station with two espresso machines, a coffee dispenser, and a tray of disposable cups.

A bathroom with a sink, mirror, towel rack, shower, and toilet.

18. Howard Johnson by Wyndham Lake George

Lake George

Laura Ann

S$106

includes taxes & fees

27 Oct - 28 Oct

An outdoor patio with a wooden pergola, stone walls, and a fire feature.

A rustic bar area with a wooden counter, coffee machines, and a variety of coffee cups and mugs.

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.

19. Super 8 by Wyndham Lake George/Downtown

Lake George

Jessika

S$103

includes taxes & fees

27 Oct - 28 Oct

A modern living room with a fireplace, a flat-screen TV mounted on the wall, and a large window.

A gym with exercise equipment, a wooden floor, and a grey carpeted area.

A Fairfield Inn & Suites hotel with a modern exterior, a stone pillar, and a well-lit entrance.

A modern bar area with a central island, bar stools, and seating.

20. Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

Queensbury

James

S$131

includes taxes & fees

15 Nov - 16 Nov

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Where to stay in Chestertown

Find the best Chestertown areas for the activities you enjoy most.

Chester Shores

Chester Shores

While Chester Shores isn't home to many top sights, Loon Lake Beach and Loon Lake are some notable places to visit nearby.

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Stay near popular Chestertown attractions

Loon Lake

8.8/10 (8 reviews)

Loon Lake's crystal-clear waters provide a peaceful Adirondack Mountain retreat for outdoor enthusiasts. Rent a kayak to glide across the serene surface or cast a line for native fish from the sandy public beach.

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Friends Lake

9.4/10 (14 reviews)

This private Adirondack gem offers pristine waters and tranquil surroundings away from tourist crowds. Stay at Friends Lake Inn to access swimming, fishing, and kayaking in this exclusive 450-acre natural retreat.

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Loon Lake Beach

8.4/10 (7 reviews)

Loon Lake Beach offers crystal-clear waters against the backdrop of the Adirondack Mountains. Enjoy a day of swimming and picnicking in this serene natural setting, where sandy shores meet lush greenery.

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Tripp Pond

8.6/10 (4 reviews)

Tripp Pond offers a tranquil escape with calm waters surrounded by lush forests in Chestertown, New York. Enjoy peaceful fishing or kayaking while taking in the natural beauty of the Adirondack landscape.

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Learn more about Chestertown

Nestled in the Adirondacks, this charming town offers hiking trails and kayaking on Friends Lake during summer months. Winter visitors can hit the slopes at nearby Gore Mountain in North Creek or explore the Natural Stone Bridge and Caves in Pottersville.

See all hotels in Chestertown

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

8/10 Good

"I stayed here just one night so as to break up a long trip of driving. There are tons of properties in this area to choose from and I like to pick a place that has a hot tub which helps me unwind from a long drive. Yep… hot tub out of order and roped off. The other selling point for me is breakfast on site so I don’t need to stop when I leave. I had a cup of coffee and part of the waffle… the rest was cold and mediocre. The bed was comfortable and the room was mostly clean. The off season rate was super reasonable so I guess you get what you pay for."

Howard Johnson by Wyndham Lake George

10/10 Excellent

"cool"

The Queensbury Hotel

10/10 Excellent

"Beautiful property"

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent

"Listen, it’s not the ritz. But it’s an extremely nice inn, in a quiet location: with well furnished rooms, in room microwaves, washer and dryer, and an extremely courteous staff. Will absolutely stay here again."

Great Escape Lodge & Indoor Waterpark

10/10 Excellent

"Our stay at the Great Escape Lodge was excellent! When checking in, staff told us where everything was located which was super helpful! We had tons of fun in the indoor water park and the arcade! The theme park is only a short walk away, which was extremely fun! I highly recommend this Lodge!"

The Georgian Lakeside Resort

10/10 Excellent

"The rooms are very clean and very neat and nice size"

Friends Lake Inn

10/10 Excellent

"Such a cute place! Beds were comfy, breakfast was delicious and staff was very kind and accommodating. Would definitely recommend!!"

More cheap stays in Chestertown

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

S$107

27 Oct - 28 Oct

includes taxes & fees

7.6/10 Good! (1,133 reviews)

Comfort Inn & Suites Lake George

4054 State Route 9L Lake George NY

S$139

24 Nov - 25 Nov

includes taxes & fees

The Georgian Lakeside Resort

384 Canada Street Lake George NY

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8.6/10 Excellent! (1,011 reviews)

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY

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Surfside On The Lake

400 Canada Street Lake George NY

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Depe Dene Lakeside Resort

3494 Lake Shore Drive Lake George NY

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Frequently asked questions

Where is the best place to stay in Chestertown?

Based on Expedia's traveller preferences, Pine Tree Motel & Cabins is a top place to stay in Chestertown. Other good choices for your stay in the area are Great Escape Lodge & Indoor Waterpark and La Quinta Inn & Suites by Wyndham Lake George. 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 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 are some accommodation options with pools in Chestertown?

La Quinta Inn & Suites by Wyndham Lake George: Hotel located near Great Escape. Features buffet, an indoor pool and free self parking. The Georgian Lakeside Resort and The Queensbury Hotel are two additional hotels that offer an on-site pool. View all hotels with pools 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.

Chestertown Hotels from S$92

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chestertown

Check prices for these dates

Filter by

Star rating

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Our top choices for Chestertown hotels

1. Friends Lake Inn

2. The Alpine Lodge

3. Courtyard by Marriott Lake George

4. La Quinta Inn & Suites by Wyndham Lake George

5. Lodge at Schroon Lake

6. Super 8 by Wyndham Lake George/Warrensburg Area

7. Comfort Inn & Suites Lake George

8. North Creek Lodge at Gore Mountain

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

10. Lodges At Cresthaven

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

12. Silver Bay YMCA Inn and Conference Center

13. Hampton Inn & Suites Lake George

14. Gore Mountain Lodge

15. Quality Inn Lake George

16. Skyline Hotel Lake George

17. Fort William Henry Hotel and Conference Center

18. Howard Johnson by Wyndham Lake George

19. Super 8 by Wyndham Lake George/Downtown

20. Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

Where to stay in Chestertown

Chester Shores

Stay near popular Chestertown attractions

Loon Lake

Friends Lake

Loon Lake Beach

Tripp Pond

Learn more about Chestertown

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

Howard Johnson by Wyndham Lake George

The Queensbury Hotel

Baymont by Wyndham Queensbury / Lake George

Great Escape Lodge & Indoor Waterpark

The Georgian Lakeside Resort

Friends Lake Inn

More cheap stays in Chestertown

Baymont by Wyndham Queensbury / Lake George

Comfort Inn & Suites Lake George

The Georgian Lakeside Resort

Adirondack Retreat Inn & Suites

Surfside On The Lake

Depe Dene Lakeside Resort

Frequently asked questions

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