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 wooden cabin room with a round table, a chair, a bed with a colorful quilt, a television, and a dog standing by the door.

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

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

1. Pine Tree Motel & Cabins

Chestertown

Andrew

฿5,794

฿6,432 total

includes taxes & fees

3 Sept - 4 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 pathway leading to a lake surrounded by dense forest and a wooden signpost.

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

2. The Fern Lodge

Chestertown

robert

฿13,269

฿14,729 total

includes taxes & fees

23 Sept - 24 Sept

3. Friends Lake Inn

Chestertown

Jonathan

฿4,447

฿4,936 total

includes taxes & fees

8 Sept - 9 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.

4. Spark by Hilton Lake George Outlets

Lake George

Maria

฿3,502

฿3,888 total

includes taxes & fees

13 Sept - 14 Sept

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 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.

5. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

Andrew

฿2,533

฿2,812 total

includes taxes & fees

15 Sept - 16 Sept

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 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.

6. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Mohammed

฿3,068

฿3,405 total

includes taxes & fees

13 Sept - 14 Sept

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 spacious room with a stone fireplace, wooden beams, and a herringbone-patterned floor.

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

7. Silver Bay YMCA Inn and Conference Center

Silver Bay

Marina

฿5,939

฿6,592 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 two-story building with a covered entrance and a sign indicating an indoor pool.

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

8. Point Hotel Queensbury

Queensbury

Chris

฿2,947

฿3,271 total

includes taxes & fees

7 Sept - 8 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 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.

9. Hampton Inn & Suites Lake George

Lake George

Jose

฿4,046

฿4,491 total

includes taxes & fees

8 Sept - 9 Sept

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 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

฿3,278

฿3,639 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 modern bar area with a central island, bar stools, and seating.

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

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

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

Queensbury

Denise

฿3,900

฿4,330 total

includes taxes & fees

8 Sept - 9 Sept

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

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.

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.

12. Courtyard by Marriott Lake George

Lake George

Blanca

฿5,629

฿6,248 total

includes taxes & fees

13 Sept - 14 Sept

An indoor water park with multiple pools, slides, and a high platform.

A spacious lobby with a high ceiling, wooden railings, a patterned carpet, and various decorative items including mounted animal heads and a chandelier.

A spacious lobby with a high ceiling, wooden beams, and a patterned carpet. There are multiple seating areas with sofas and tables, and a staircase leading to an upper level.

13. Great Escape Lodge & Indoor Waterpark

Queensbury

Tammy

฿6,059

฿6,725 total

includes taxes & fees

27 Sept - 28 Sept

A lobby with a checkered floor, a chandelier, and a sign reading "The Queensbury."

A building with a sign reading "Queensbury" and "The Queensbury Hotel" with columns and a covered entrance.

A checkered floor, a fireplace, a dining table, and a chandelier in a room with a painting on the wall.

A restaurant with high ceilings, arched windows, and modern lighting. Tables are set with white tablecloths and silverware.

14. The Queensbury Hotel

Glens Falls

Kimberly

฿3,993

฿4,432 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

A reception area with a counter, seating, a TV, and informational posters.

15. Howard Johnson by Wyndham Lake George

Lake George

Brian

฿2,616

฿2,904 total

includes taxes & fees

14 Sept - 15 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 refrigerator, microwave, and dishwasher, a flat-screen TV, a desk with a chair, and a patterned carpet.

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

A modern hotel with a prominent 'HOME 2' sign, multiple floors, and a covered parking area.

16. Home2 Suites by Hilton Queensbury Lake George

Queensbury

Amy

฿4,988

฿5,536 total

includes taxes & fees

24 Sept - 25 Sept

A hotel room with a bed, a desk with a computer, a TV, and a microwave.

17. Red Roof Inn Queensbury

Queensbury

Luis

฿2,135

฿2,370 total

includes taxes & fees

6 Sept - 7 Sept

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.

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

Lake George

Tina

฿4,934

฿5,476 total

includes taxes & fees

7 Sept - 8 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 swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

19. Admiral Motel

Lake George

Grayson

฿2,467

฿2,739 total

includes taxes & fees

2 Sept - 3 Sept

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

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

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.

20. Quality Inn Lake George

Lake George

David

฿3,939

฿4,372 total

includes taxes & fees

29 Sept - 30 Sept

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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

A snowy lodge with cabins and tall pine trees.

Top Chestertown Hotel Reviews

Baymont by Wyndham Queensbury / Lake George

8/10 Good

"Room was clean, plenty of parking had a pool."

Adirondack Retreat Inn & Suites

8/10 Good

"Positives: Property was well maintained and had a nice pool, playground, and picnic/grilling area. Check-in to our room was very easy and the front desk staff was friendly. The location of the property was convenient to walk into town. Beds were very comfortable, bathroom was clean, and great water pressure in the shower. Room for improvement: The couch in our room had several stains."

The Queensbury Hotel

10/10 Excellent

"This excellent historic hotel always surpasses expectations. Stayed many times. It’s really cozy in the winter. Right downtown within walking distance of everything."

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."

The Georgian Lakeside Resort

8/10 Good

"Honestly the room are old but was clean"

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."

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

8/10 Good

"We thought this hotel was ideal as far as location. It was right next door to Great Escape Amusement park, ice cream stand across the street, mini golf close by with go carts, roller skating, laser tag, rope course. Restaurants and bars close by. Lake George was 10 minutes away. Saratoga was approximately 20 minutes away. Our room was clean, well maintained and stocked. We had a suite with 2 Queen beds and a pull-out couch on the other side for the kids. Mini fridge, microwave, coffee pot. Free breakfast with plenty of options. The kids loved the indoor pool and hot tub, and outdoor pool as well. And the large fire pit out front was a great place to relax at night. We would definitely stay here again. Staff was very accommodating and friendly."

La Quinta Inn & Suites by Wyndham Lake George

8/10 Good

"Our stay was nice. However, I found it a little frustrating that no one was at the front desk almost everytime we went to make inquiries. We either had to call the number shown on the signs or ring a bell and wait. Additionally, the coffee station was poorly kept. Either no cups, no hot water or untidy."

Surfside On The Lake

10/10 Excellent

"Clean. Close to town. Pool area was great. Pool service for food and drinks. Beach area nice"

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY

฿1,998

฿2,218 total

7 Sept - 8 Sept

includes taxes & fees

5.4/10 (1,004 reviews)

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

฿2,503

฿2,779 total

20 Sept - 21 Sept

includes taxes & fees

7.6/10 Good! (1,093 reviews)

Howard Johnson by Wyndham Lake George

99 Canada St Lake George NY

฿2,616

฿2,904 total

14 Sept - 15 Sept

includes taxes & fees

The Georgian Lakeside Resort

384 Canada Street Lake George NY

฿3,609

฿4,006 total

13 Sept - 14 Sept

includes taxes & fees

8.6/10 Excellent! (1,014 reviews)

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY

฿3,609

฿4,150 total

3 Sept - 4 Sept

includes taxes & fees

9.4/10 Exceptional! (1,017 reviews)

Comfort Inn & Suites Lake George

4054 State Route 9L Lake George NY

฿3,844

฿4,267 total

8 Sept - 9 Sept

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 The Queensbury Hotel 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?

The Queensbury Hotel: Provides 2 restaurants, an indoor pool and 2 bars. La Quinta Inn & Suites by Wyndham Lake George and Holiday Inn Resort Lake George - Adirondack Area by IHG 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 Friends Lake, Loon Lake and Hudson River. A couple of additional sights to add to your itinerary are Loon Lake Beach 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 ฿2,218

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. Pine Tree Motel & Cabins

2. The Fern Lodge

3. Friends Lake Inn

4. Spark by Hilton Lake George Outlets

5. Super 8 by Wyndham Lake George/Warrensburg Area

6. La Quinta Inn & Suites by Wyndham Lake George

7. Silver Bay YMCA Inn and Conference Center

8. Point Hotel Queensbury

9. Hampton Inn & Suites Lake George

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

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

12. Courtyard by Marriott Lake George

13. Great Escape Lodge & Indoor Waterpark

14. The Queensbury Hotel

15. Howard Johnson by Wyndham Lake George

16. Home2 Suites by Hilton Queensbury Lake George

17. Red Roof Inn Queensbury

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

19. Admiral Motel

20. Quality Inn 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

Baymont by Wyndham Queensbury / Lake George

Adirondack Retreat Inn & Suites

The Queensbury Hotel

Scotty's Lakeside Resort

The Georgian Lakeside Resort

Depe Dene Lakeside Resort

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

La Quinta Inn & Suites by Wyndham Lake George

Surfside On The Lake

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

Baymont by Wyndham Queensbury / Lake George

Howard Johnson by Wyndham Lake George

The Georgian Lakeside Resort

Adirondack Retreat Inn & Suites

Comfort Inn & Suites Lake George

Frequently asked questions

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