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

A small, single-story house with a gabled roof and a front porch.

A room with wooden walls, a bed, a dresser, a television, and a small refrigerator.

A wooden arbor structure in a grassy area with two potted plants.

A small wooden cabin with a porch and two chairs in front.

1. Pine Tree Motel & Cabins

Chestertown

Andrew

4.562.775 ₫

5.064.680 ₫ total

includes taxes & fees

7 Sept - 8 Sept

2. Friends Lake Inn

Chestertown

Jonathan

3.457.412 ₫

3.837.571 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

3. The Fern Lodge

Chestertown

robert

10.433.250 ₫

11.580.908 ₫ total

includes taxes & fees

23 Sept - 24 Sept

An indoor swimming pool with a view of the city through large windows, a seating area with chairs, and a ceiling with exposed beams.

A row of white single-story buildings with a paved driveway and tall evergreen trees in front.

A hotel reception desk with a wooden counter, two computer monitors, and a colorful abstract painting above.

A modern building with a parking lot and a fenced area.

4. Spark by Hilton Lake George Outlets

Lake George

Maria

2.758.108 ₫

3.061.499 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A hotel room with two beds, a desk, a chair, a lamp, and two framed pictures on the wall.

A living room with a sofa, armchair, and coffee table, two windows with curtains, and a tiled floor.

A dining area with a table and chairs, a sofa, and a view through a door.

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

5. Point Hotel Queensbury

Queensbury

Chris

2.320.497 ₫

2.575.752 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

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.

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

Andrew

1.861.612 ₫

2.066.546 ₫ total

includes taxes & fees

7 Sept - 8 Sept

7. The Queensbury Hotel

Glens Falls

Kimberly

2.935.672 ₫

3.258.468 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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.

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

Queensbury

Denise

3.443.072 ₫

3.821.810 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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 with a prominent 'LAQUINTA' sign, a covered entrance, and a parking lot.

9. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Mohammed

2.415.756 ₫

2.681.489 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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.

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

Queensbury

KELLY

2.487.103 ₫

2.760.684 ₫ total

includes taxes & fees

24 Sept - 25 Sept

A rooftop terrace with lounge chairs and tables, overlooking a lake and mountains.

A swimming pool with chairs and tables around it, large windows, and a tiled floor.

A multi-story hotel with balconies, a stone facade, and a green roof.

A spacious banquet hall with round tables and chairs, large windows, and ceiling lights.

11. Courtyard by Marriott Lake George

Lake George

Yasmeen

3.728.439 ₫

4.138.568 ₫ total

includes taxes & fees

9 Sept - 10 Sept

A modern hotel entrance with a covered waiting area, stone pillars, and a blue-lit facade.

A modern restaurant with wooden tables and chairs, a bar area, and a patterned booth seating.

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.

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

Queensbury

Alicia

3.076.732 ₫

3.415.173 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A reception area with a wooden counter, a welcome sign, and a ship's wheel decoration.

A white building with a yellow awning, a porch with flowers, and American flags.

A poolside area with a blue sofa, white wicker chairs, and a small table with a basket.

A wooden bear sculpture with a sign reading "Admiral Motel" in front of a building with outdoor seating.

13. Admiral Motel

Lake George

Grayson

1.943.034 ₫

2.156.769 ₫ total

includes taxes & fees

7 Sept - 8 Sept

An indoor swimming pool with a clear water surface, a diving board, and lounge chairs around the pool area.

A hotel lobby with a sofa, a round table with a flower vase, a lamp, and a large window with a view.

A Sleep Inn hotel with a prominent sign, a well-lit entrance, and a landscaped front yard.

A hotel reception area with a wooden reception desk, a check-in counter, and a staircase leading to an upper level.

14. Sleep Inn & Suites Queensbury - Lake George

Queensbury

Frederick

2.273.653 ₫

2.523.754 ₫ total

includes taxes & fees

24 Sept - 25 Sept

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.

15. Hampton Inn & Suites Lake George

Lake George

Jose

3.292.625 ₫

3.654.814 ₫ total

includes taxes & fees

13 Sept - 14 Sept

An outdoor patio area with a fire pit, yellow and red outdoor seating, and a covered wooden structure with string lights.

A modern kitchen with a built-in microwave, coffee maker, and dishwasher.

A hotel room with two beds, a desk, a chair, a TV, a wardrobe, and a bathroom.

A modern kitchen with a refrigerator, microwave, and dishwasher, a flat-screen TV, a desk with a chair, and a patterned carpet.

16. Home2 Suites by Hilton Queensbury Lake George

Queensbury

Amy

2.978.694 ₫

3.306.351 ₫ total

includes taxes & fees

9 Sept - 10 Sept

A hotel room with a bed, a desk, a chair, a microwave, and a television on the wall.

A bathroom with a sink, toilet, and bathtub.

A motel with a single-story structure, a covered parking area, and a small front porch.

A hotel room with a bed, a desk with a chair, a microwave, and a television on the wall.

17. Blue Line Inn Lake George

Lake George

Daniel

3.690.775 ₫

4.096.761 ₫ total

includes taxes & fees

4 Sept - 5 Sept

A hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.

A restaurant with wooden tables and chairs, a kitchen area, and a counter with food items.

An indoor swimming pool with clear water, red safety flooring, and lounge chairs along the wall.

A hotel lobby with leather sofas, a reception desk, a television, and a sign for 'Baymont.'

18. Baymont by Wyndham Queensbury / Lake George

Queensbury

Lisa

1.947.728 ₫

2.161.979 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a painting above the bed.

A breakfast area with a sign for 'Daybreak' and a display of fresh baked waffles.

A gym with orange walls, a treadmill, and various exercise equipment.

19. Days Inn by Wyndham Queensbury/Lake George

Queensbury

RESHMA

1.573.566 ₫

1.746.659 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

A hotel room with a large bed, a bench, a TV, and a window with curtains.

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.

20. Comfort Inn & Suites Lake George

Lake George

Deborah

3.027.191 ₫

3.360.182 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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Where to stay in Chestertown

Find the best Chestertown areas for the activities you enjoy most.Learn more about Chestertown

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

A snowy lodge with cabins and tall pine trees.

Top Chestertown Hotel Reviews

Lakefront Terrace Resort

10/10 Excellent

"It was a great stay!"

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

10/10 Excellent

"All around a great experience."

Baymont by Wyndham Queensbury / Lake George

8/10 Good

"My room was clean and things like shampoo, conditioner, bodywash, towels, cups, etc were provided. At first I couldn't get the fridge to close all the way, but after some pushing it finally closed and was good for the rest of the stay and kept things cold. The beds were comfortable and the carpet clean. The air conditioning worked well, but a little loud. The continental breakfast offered a variety of foods, but no meats, like sausage or bacon to go with the eggs or waffles. The staff was polite and helpful. They don't do daily housekeeping, but if you ask for clean towels or whatever you need, they will provide it. On our 3rd day we asked for a complete housekeeping and it was done when we got back. I didn't see the pool, but I heard that it was good."

Nordick's Inn

10/10 Excellent

"The Nordick Hotel is a great place to stay. The owners and the office worker Danny are so friendly. The place is very clean and they go out of their way to make your stay perfect, it is located right on the strip and very close to everything. I highly recommend this hotel."

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent

"The Holiday Inn Resort in Lake George is amazing. They have a board that welcomes people that are checking in with their name on it. The outdoor pool, play area, basketball court and dj at the pool are great. Wonderful place for families. There is a video game room, theatre, and a very nice restaurant and bar. I was very impressed. The Inn was very clean and great staff. I would definitely stay there again."

Lodge at Schroon Lake

10/10 Excellent

"Amazing stay"

Adirondack Retreat Inn & Suites

10/10 Excellent

"Everything was clean, convenient, and comfortable. If you are staying on the first floor, you can hear people walking above you, though."

Scotty's Lakeside Resort

8/10 Good

"Room was clean, beds comfortable, shower was good. Only drawback was the a/c unit which emitted smelly air...mildewy? Nice location at the edge of the busy part of town, walkable to restaurants. I was impressed with the beautiful fresh flower hanging baskets on every porch, the outside area is nice, pool looked great, front desk staff very pleasant. Seems like a good place for families with kids."

Depe Dene Lakeside Resort

10/10 Excellent

"Enjoyed our room with the view (amazing view). All good and clean (please use less Pine sol or similar smelly cleaners).Location, beach, beds all good."

More cheap stays in Chestertown

Super 8 by Wyndham Lake George/Warrensburg Area

3619 State Route 9 Lake George NY

1.861.612 ₫

2.066.546 ₫ total

7 Sept - 8 Sept

includes taxes & fees

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

1.947.728 ₫

2.161.979 ₫ total

14 Sept - 15 Sept

includes taxes & fees

7.6/10 Good! (1,091 reviews)

Howard Johnson by Wyndham Lake George

99 Canada St Lake George NY

1.955.550 ₫

2.170.661 ₫ total

21 Sept - 22 Sept

includes taxes & fees

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY

2.131.467 ₫

2.451.188 ₫ total

21 Sept - 22 Sept

includes taxes & fees

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY

2.758.108 ₫

3.061.499 ₫ total

13 Sept - 14 Sept

includes taxes & fees

The Georgian Lakeside Resort

384 Canada Street Lake George NY

2.841.957 ₫

3.154.572 ₫ total

21 Sept - 22 Sept

includes taxes & fees

8.8/10 Excellent! (1,001 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 2.066.546 ₫

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. Pine Tree Motel & Cabins

2. Friends Lake Inn

3. The Fern Lodge

4. Spark by Hilton Lake George Outlets

5. Point Hotel Queensbury

6. Super 8 by Wyndham Lake George/Warrensburg Area

7. The Queensbury Hotel

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

9. La Quinta Inn & Suites by Wyndham Lake George

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

11. Courtyard by Marriott Lake George

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

13. Admiral Motel

14. Sleep Inn & Suites Queensbury - Lake George

15. Hampton Inn & Suites Lake George

16. Home2 Suites by Hilton Queensbury Lake George

17. Blue Line Inn Lake George

18. Baymont by Wyndham Queensbury / Lake George

19. Days Inn by Wyndham Queensbury/Lake George

20. Comfort Inn & Suites Lake George

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

Lakefront Terrace Resort

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

Baymont by Wyndham Queensbury / Lake George

Nordick's Inn

Holiday Inn Resort Lake George - Adirondack Area by IHG

Lodge at Schroon Lake

Adirondack Retreat Inn & Suites

Scotty's Lakeside Resort

Depe Dene Lakeside Resort

More cheap stays in Chestertown

Super 8 by Wyndham Lake George/Warrensburg Area

Baymont by Wyndham Queensbury / Lake George

Howard Johnson by Wyndham Lake George

Adirondack Retreat Inn & Suites

Spark by Hilton Lake George Outlets

The Georgian Lakeside Resort

Hotels in Chestertown with star rating

Frequently asked questions

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