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

Rp1.945.889

Rp2.160.129 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 pathway leading to a lake surrounded by dense forest and a wooden signpost.

2. The Fern Lodge

Chestertown

robert

Rp7.182.218

Rp7.972.263 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 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.

3. Courtyard by Marriott Lake George

Lake George

SANDRA

Rp2.219.476

Rp2.463.618 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Lake George

JAEHYUN

Rp2.006.256

Rp2.226.944 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 hotel room with a large bed, a bench, a TV, and a window with curtains.

5. Comfort Inn & Suites Lake George

Lake George

Artyom

Rp1.811.721

Rp2.011.011 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

6. Lodges At Cresthaven

Lake George

Lourdes

Rp2.664.548

Rp2.957.649 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 living area with a staircase, a fireplace, a sofa, and a coffee table.

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

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

Queensbury

Nicole

Rp1.415.844

Rp1.571.587 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 kitchen with wooden cabinets, stainless steel appliances, granite countertops, and pendant lighting.

8. The Alpine Lodge

North Creek

Richard

Rp2.305.986

Rp2.751.133 total

includes taxes & fees

29 Oct - 30 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 lakeside property with docked boats, a stone pathway, and a view of the surrounding forest and buildings.

9. Lodge at Schroon Lake

Schroon Lake

Marco

Rp2.450.498

Rp3.356.071 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

Queensbury

James

Rp1.769.804

Rp1.964.482 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

11. Hampton Inn & Suites Lake George

Lake George

PATRICIA

Rp1.811.900

Rp2.011.209 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

A patio area with a stone fire pit, white outdoor furniture, and a white picket fence.

12. Quality Inn Lake George

Lake George

Andrea

Rp2.095.104

Rp2.325.565 total

includes taxes & fees

3 Nov - 4 Nov

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

A conference room with round tables, black leather chairs, and a chandelier.

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

13. The Queensbury Hotel

Glens Falls

Patricia

Rp1.999.091

Rp2.218.704 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

14. Fort William Henry Hotel and Conference Center

Lake George

IMTIAZ

Rp1.688.614

Rp2.214.710 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A beach with white lounge chairs and a pier extending into the water.

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

15. The Juliana Resort

Diamond Point

Julia

Rp1.952.517

Rp2.167.294 total

includes taxes & fees

14 Oct - 15 Oct

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 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.

16. The Georgian Lakeside Resort

Lake George

cait

Rp1.952.517

Rp2.167.295 total

includes taxes & fees

14 Oct - 15 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 hotel pool area with multiple pools, lounge chairs, and a covered seating area.

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

17. Skyline Hotel Lake George

Lake George

Alessandro

Rp1.293.203

Rp1.435.455 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

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

Queensbury

Carlos

Rp1.719.648

Rp1.908.809 total

includes taxes & fees

8 Nov - 9 Nov

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 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.

19. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Michael

Rp1.506.201

Rp1.671.883 total

includes taxes & fees

1 Nov - 2 Nov

An aerial view of a lakeside property with a dock, a gazebo, and a large house with a porch.

A grand wooden staircase with a handrail, leading to a high ceiling with a chandelier.

A beach with rows of red chairs and a dock with boats.

A modern living room with a sofa, coffee table, and artwork on the walls.

20. Depe Dene Lakeside Resort

Lake George

Jessica

Rp1.757.265

Rp1.950.367 total

includes taxes & fees

14 Oct - 15 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

Nordick's Inn

8/10 Good

"We had a great stay at the Nordic Inn in Lake George! The location was perfect for enjoying everything the area has to offer, and the overall experience made for a wonderful getaway. The place was comfortable, welcoming, and a great value. We really enjoyed our time here and would definitely consider staying again on our next trip to Lake George."

Fort William Henry Hotel and Conference Center

8/10 Good

"Everything Breakfast staff I felt was a little slower then would have liked"

The Queensbury Hotel

10/10 Excellent

"Wonderful older hotel that's well maintained, beautifully undated and perfectly located in a very neat town - GLENS FALLS, NY. Will definitely return someday. STAFF lady whom checked us in and out was one of the sweetest and kindest ever!"

Lodge at Schroon Lake

10/10 Excellent

"This property is incredible. It's like stepping back into the Dirty Dancing movie but with all the modern amenities. The staff was outstanding."

Great Escape Lodge & Indoor Waterpark

10/10 Excellent

"We have gone several times with our family of 4 and always have a blast!"

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"

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."

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY

Rp1.050.597

Rp1.166.163 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

Rp1.353.164

Rp1.502.013 total

15 Oct - 16 Oct

includes taxes & fees

7.6/10 Good! (1,133 reviews)

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY

Rp1.384.317

Rp1.536.577 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

Rp1.757.265

Rp2.020.854 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

Rp1.952.517

Rp2.167.295 total

14 Oct - 15 Oct

includes taxes & fees

Surfside On The Lake

400 Canada Street Lake George NY

Rp1.640.383

Rp2.268.651 total

14 Oct - 15 Oct

includes taxes & fees

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 Rp1.166.163

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chestertown

Check prices for these dates

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Our top choices for Chestertown hotels

1. Friends Lake Inn

2. The Fern Lodge

3. Courtyard by Marriott Lake George

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

5. Comfort Inn & Suites Lake George

6. Lodges At Cresthaven

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

8. The Alpine Lodge

9. Lodge at Schroon Lake

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

11. Hampton Inn & Suites Lake George

12. Quality Inn Lake George

13. The Queensbury Hotel

14. Fort William Henry Hotel and Conference Center

15. The Juliana Resort

16. The Georgian Lakeside Resort

17. Skyline Hotel Lake George

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

19. La Quinta Inn & Suites by Wyndham Lake George

20. Depe Dene Lakeside Resort

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

Nordick's Inn

Fort William Henry Hotel and Conference Center

The Queensbury Hotel

Lodge at Schroon Lake

Great Escape Lodge & Indoor Waterpark

Adirondack Retreat Inn & Suites

Tiki Resort

Lakefront Terrace Resort

Depe Dene Lakeside Resort

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

Frequently asked questions

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