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

฿3,502

฿3,887 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

A pathway leading to a lake surrounded by dense forest and a wooden signpost.

2. The Fern Lodge

Chestertown

robert

฿13,438

฿14,916 total

includes taxes & fees

12 Nov - 13 Nov

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

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.

A Comfort Inn & Suites sign with a blue background and a yellow stripe.

3. Comfort Inn & Suites Lake George

Lake George

Artyom

฿3,381

฿3,752 total

includes taxes & fees

8 Nov - 9 Nov

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

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

4. Courtyard by Marriott Lake George

Lake George

Bob

฿4,145

฿4,600 total

includes taxes & fees

2 Nov - 3 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 lobby with a reception desk, seating area, stone fireplace, and large windows.

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.

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

Lake George

suzanne

฿3,743

฿4,155 total

includes taxes & fees

16 Nov - 17 Nov

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

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.

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

6. Lodge at Schroon Lake

Schroon Lake

Marco

฿4,302

฿5,956 total

includes taxes & fees

12 Nov - 13 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.

7. Hampton Inn & Suites Lake George

Lake George

PATRICIA

฿3,447

฿3,826 total

includes taxes & fees

28 Oct - 29 Oct

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".

8. The Alpine Lodge

North Creek

Patricia

฿4,227

฿5,049 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

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

Queensbury

James

฿3,302

฿3,666 total

includes taxes & fees

16 Nov - 17 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 hotel room with a kitchenette, a bed, a desk, a chair, and a large mirror.

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

Nicole

฿2,642

฿2,932 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

11. Quality Inn Lake George

Lake George

Andrea

฿3,920

฿4,351 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

A modern hotel lobby with a seating area, a bar, and a kitchen in the background.

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

Queensbury

Carlos

฿3,217

฿3,571 total

includes taxes & fees

8 Nov - 9 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 lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.

A snow-covered lodge with cabins, a clear view of a lake, and mountains in the background.

13. Lodges At Cresthaven

Lake George

Lisa

฿3,027

฿3,360 total

includes taxes & fees

12 Nov - 13 Nov

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

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

A hotel pool area with multiple pools, lounge chairs, and a covered seating area.

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

14. Skyline Hotel Lake George

Lake George

Alessandro

฿2,415

฿2,681 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

15. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

James

฿2,386

฿2,649 total

includes taxes & fees

8 Nov - 9 Nov

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 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.

16. The Georgian Lakeside Resort

Lake George

cait

฿3,643

฿4,044 total

includes taxes & fees

18 Oct - 19 Oct

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 gym with treadmills, an elliptical, a bench press, a water dispenser, and a TV on the wall.

A residential area with two-story buildings, a well-maintained lawn, and a clear sky.

A hotel room with a large bed, bedside tables, a desk, and a window with curtains.

17. Spark by Hilton Lake George Outlets

Lake George

Julie Van

฿2,583

฿2,867 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

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

18. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Michael

฿2,813

฿3,122 total

includes taxes & fees

2 Nov - 3 Nov

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

A hotel room with two beds, a sofa, a colorful ottoman, a painting on the wall, and a large window.

A modern building with a flat roof, concrete structures, and a paved area with small plants.

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

19. Home2 Suites by Hilton Queensbury Lake George

Queensbury

Lynne

฿3,536

฿3,925 total

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

20. Fort William Henry Hotel and Conference Center

Lake George

IMTIAZ

฿3,276

฿4,274 total

includes taxes & fees

18 Oct - 19 Oct

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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

Surfside On The Lake

10/10 Excellent

"Great spot in Lake placid with wonderful views and rooms!"

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent

"Thank you to all the Family I’ll shall see you soon"

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good

"The hotel and the property is gorgeous! The staff were all friendly and the food in the restaurant was very good. The only problem was when we came back at night after being at an outdoor wedding and I was freezing cold. We had no hot water. I was not able to take the shower that I so desperately wanted .When I mentioned it to the staff in the morning when we were checking out, they simply apologized but had no reason why there was no hot water in our room. That was disappointing. It was 5:30 in the morning, I was rushing to catch a flight, so I did not pursue it further with the management."

Howard Johnson by Wyndham Lake George

10/10 Excellent

"Very enjoyable stay will return"

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"Clean"

Courtyard by Marriott Lake George

10/10 Excellent

"The location was perfect and staff were excellent. The only thing missing was a coffee and tea bar."

Depe Dene Lakeside Resort

10/10 Excellent

"The lake views were amazing!! The room was big and clean, nice amenities. However the grounds are hard to Navigate. It is a very steep hill bumpy road not well maintained roads"

Tiki Resort

10/10 Excellent

"Clean room, easy parking, helpful staff. Stayed for 1 night, no complains."

Great Escape Lodge & Indoor Waterpark

8/10 Good

"Had to walk to far from checking in to my room! Room number was 305! My wife has Parkinson’s and it was very difficult for her to walk that distance!"

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY

฿1,881

฿2,087 total

27 Oct - 28 Oct

includes taxes & fees

5.4/10 (1,002 reviews)

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

฿2,527

฿2,805 total

19 Oct - 20 Oct

includes taxes & fees

7.6/10 Good! (1,129 reviews)

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY

฿2,583

฿2,867 total

15 Nov - 16 Nov

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

The Georgian Lakeside Resort

384 Canada Street Lake George NY

฿3,643

฿4,044 total

18 Oct - 19 Oct

includes taxes & fees

Surfside On The Lake

400 Canada Street Lake George NY

฿3,715

฿4,962 total

18 Oct - 19 Oct

includes taxes & fees

8/10 Very good! (865 reviews)

Adirondack Retreat Inn & Suites

435 Canada Street 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.

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Book Hotels in Chestertown on Expedia.com

Find hotels in Chestertown, NY from ฿2,087

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chestertown

Check prices for these dates

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Star rating

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Our top choices for Chestertown hotels

1. Friends Lake Inn

2. The Fern Lodge

3. Comfort Inn & Suites Lake George

4. Courtyard by Marriott Lake George

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

6. Lodge at Schroon Lake

7. Hampton Inn & Suites Lake George

8. The Alpine Lodge

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

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

11. Quality Inn Lake George

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

13. Lodges At Cresthaven

14. Skyline Hotel Lake George

15. Super 8 by Wyndham Lake George/Warrensburg Area

16. The Georgian Lakeside Resort

17. Spark by Hilton Lake George Outlets

18. La Quinta Inn & Suites by Wyndham Lake George

19. Home2 Suites by Hilton Queensbury Lake George

20. Fort William Henry Hotel and Conference Center

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

Surfside On The Lake

Baymont by Wyndham Queensbury / Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

Howard Johnson by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

Courtyard by Marriott Lake George

Depe Dene Lakeside Resort

Tiki Resort

Great Escape Lodge & Indoor Waterpark

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

Baymont by Wyndham Queensbury / Lake George

Spark by Hilton Lake George Outlets

The Georgian Lakeside Resort

Surfside On The Lake

Adirondack Retreat Inn & Suites

Frequently asked questions

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