Chestertown Holiday Rentals, New York: Private House Rentals

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

2.850.060 ₫

3.163.629 ₫ total

includes taxes & fees

22 Oct - 23 Oct

A lakeside setting with a boat docked near the shore, surrounded by trees and a fire pit area with seating.

A large, multi-story log cabin with a prominent chimney, surrounded by dense forest and rocky terrain.

A wooden cabin interior with a stone fireplace, a wooden bathtub, and a view of a lake.

A cozy room with a stone fireplace, a comfortable sofa, and a table with books and snacks.

2. The Fern Lodge

Chestertown

robert

10.397.435 ₫

11.541.154 ₫ total

includes taxes & fees

15 Oct - 16 Oct

Two people dining at an outdoor table with a pizza and drinks, overlooking a lake with a boat and hills in the background.

A bar area with wooden chairs, a counter with a glass display, and hanging lights.

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

A couple sitting on a green sofa in a hotel lobby with a tiled floor and wooden shelves in the background.

3. Courtyard by Marriott Lake George

Lake George

SANDRA

3.215.568 ₫

3.569.280 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A snack and beverage vending area with various snack boxes and a Pepsi refrigerator.

A spacious lobby with a high ceiling, a staircase, and a reception desk.

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.

4. Comfort Inn & Suites Lake George

Lake George

Artyom

2.622.762 ₫

2.911.267 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A patio area with a stone fire pit, wooden chairs, and tables, surrounded by a building with large windows and a stone facade.

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

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.

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

Lake George

JAEHYUN

2.904.384 ₫

3.223.865 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

A lakeside property with docked boats, a stone pathway, and a view of the surrounding forest and buildings.

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.

6. Lodge at Schroon Lake

Schroon Lake

Marco

3.547.498 ₫

4.858.361 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

7. Lodges At Cresthaven

Lake George

Lourdes

3.857.369 ₫

4.281.680 ₫ total

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

A spacious living area with a staircase, a fireplace, a sofa, and a coffee table.

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

Queensbury

Nicole

2.049.665 ₫

2.275.129 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

A two-story building with a dark exterior, a covered front porch, and a sign reading "TALPINE LODGE".

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

9. The Alpine Lodge

North Creek

Richard

3.331.227 ₫

3.974.233 ₫ total

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

A swimming pool with clear water, a lifeguard chair, and a no diving sign.

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

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

Queensbury

James

2.562.082 ₫

2.843.911 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

11. Quality Inn Lake George

Lake George

Andrea

3.033.007 ₫

3.366.637 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

A spacious lobby with a stone fireplace, blue seating, and a large chandelier.

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

12. Hampton Inn & Suites Lake George

Lake George

PATRICIA

2.623.022 ₫

2.911.553 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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.

13. Fort William Henry Hotel and Conference Center

Lake George

IMTIAZ

2.444.545 ₫

3.206.154 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A poolside area with lounge chairs and umbrellas, a bar, and a view of the sea and mountains at night.

A table with a meal, a drink, and a view of the sea.

A marina with docked boats, a covered seating area, and a view of a lake with mountains in the background.

A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.

14. The Georgian Lakeside Resort

Lake George

cait

2.820.048 ₫

3.130.253 ₫ total

includes taxes & fees

16 Oct - 17 Oct

A hotel room with two beds, a map on the wall, and a door.

A gym with various weightlifting equipment, including dumbbells and a bench.

A room with a dark wooden floor, a red chair, a black desk, and a framed black and white photograph on the wall.

15. The Queensbury Hotel

Glens Falls

2.887.315 ₫

3.204.506 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk with a television, and a window with curtains.

A hotel room with a television, sofa, armchair, dining table, and chairs.

A dining area with a table and chairs, a kitchen area with a microwave and stove, and a television in the living room.

A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a coffee maker on the countertop.

16. Skyline Hotel Lake George

Lake George

Alessandro

1.869.252 ₫

2.074.870 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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.

A hotel reception area with a modern design, featuring a reception desk, a digital screen, and a wooden floor.

An outdoor patio with tables and chairs, large windows, and a stone wall.

17. Holiday Inn Express Queensbury - Lake George Area by IHG

Queensbury

2.489.472 ₫

2.763.314 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A lakeside patio with wooden chairs, a fire pit, and boats in the background.

A waterfront deck with lounge chairs, a sailboat, and a dock extending into calm water.

A wooden building with a balcony, a clock, and a lifebuoy.

A living room with a stone fireplace, leather furniture, and a chandelier.

18. The Juliana Resort

Diamond Point

Julia

2.826.588 ₫

3.137.513 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

19. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Michael

2.182.178 ₫

2.422.218 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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 wooden cabin with a picnic table and a barbecue grill.

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

20. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

James

1.851.545 ₫

2.055.371 ₫ total

includes taxes & fees

8 Nov - 9 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

Adirondack Retreat Inn & Suites

10/10 Excellent

"Clean, updated rooms, friendly staff."

Tiki Resort

8/10 Good

"every thing was great but on our side of the hotel we didn’t have wifi and the kids were a little upset i think the hotel was very clean and the staff was nice but i think they need to update their servers for the wifi to accommodate the entire hotel so everyone staying can have access to the internet"

Great Escape Lodge & Indoor Waterpark

10/10 Excellent

"rooms were clean ,staff were very friendly and helpful ,kids really enjoyed the swimming are, they never wanted to leave the park."

The Queensbury Hotel

8/10 Good

"Rooms were clean and beds comfortable. The pool area was lovely. Mobility impaired guests may have challenges with this historic hotel but staff are accommodating."

Lakefront Terrace Resort

8/10 Good

"The view from our room was great! We were right on the lake."

Depe Dene Lakeside Resort

10/10 Excellent

"It was great! Was here for a wedding for two days, and the 3 bedroom cabin easily and comfortably fit 6 adults. It was nice to have room to spread out and all have our own space. My mom questioned if the heater/AC would be enough for the whole cabin because it’s in the living room and it was a cold weekend, but it cranked and we had to turn in down at bedtime because it was a little hot. Overall a cute place, with a good lake view and comfortable cabin. Would definitely stay again."

Surfside On The Lake

10/10 Excellent

"The staff was helpful and the room was clean"

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent

"everything good and valued"

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good

"We loved staying there. Very clean, helpful happy staff and good food. Top it all off with a beautiful view of Lake George from several windowd."

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY

1.520.912 ₫

1.688.214 ₫ total

1 Nov - 2 Nov

includes taxes & fees

5.4/10 (1,005 reviews)

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

1.955.923 ₫

2.171.074 ₫ total

18 Oct - 19 Oct

includes taxes & fees

7.6/10 Good! (1,129 reviews)

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY

2.004.025 ₫

2.224.447 ₫ total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,005 reviews)

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY

2.543.929 ₫

2.925.518 ₫ total

14 Oct - 15 Oct

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

The Georgian Lakeside Resort

384 Canada Street Lake George NY

2.820.048 ₫

3.130.253 ₫ total

16 Oct - 17 Oct

includes taxes & fees

Surfside On The Lake

400 Canada Street Lake George NY

2.369.228 ₫

3.276.643 ₫ total

18 Oct - 19 Oct

includes taxes & fees

8/10 Very good! (857 reviews)

Hotels in Chestertown with star rating

Frequently asked questions

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.

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Book Hotels in Chestertown on Expedia.com

Find hotels in Chestertown, NY from 1.688.214 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chestertown

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chestertown hotels

1. Friends Lake Inn

2. The Fern Lodge

3. Courtyard by Marriott Lake George

4. Comfort Inn & Suites Lake George

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

6. Lodge at Schroon Lake

7. Lodges At Cresthaven

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

9. The Alpine Lodge

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

11. Quality Inn Lake George

12. Hampton Inn & Suites Lake George

13. Fort William Henry Hotel and Conference Center

14. The Georgian Lakeside Resort

15. The Queensbury Hotel

16. Skyline Hotel Lake George

17. Holiday Inn Express Queensbury - Lake George Area by IHG

18. The Juliana Resort

19. La Quinta Inn & Suites by Wyndham Lake George

20. Super 8 by Wyndham Lake George/Warrensburg 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

Adirondack Retreat Inn & Suites

Tiki Resort

Great Escape Lodge & Indoor Waterpark

The Queensbury Hotel

Lakefront Terrace Resort

Depe Dene Lakeside Resort

Surfside On The Lake

Baymont by Wyndham Queensbury / Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

Baymont by Wyndham Queensbury / Lake George

Spark by Hilton Lake George Outlets

Adirondack Retreat Inn & Suites

The Georgian Lakeside Resort

Surfside On The Lake

Hotels in Chestertown with star rating

Frequently asked questions

Explore a world of travel with Expedia

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