𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chestertown from RM298 (2026) - Fully Refundable Options

A waterfront town with a pier, dock, and several buildings.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Chestertown

Pet friendly

Hot tub

Pool

Apartment

Family friendly

Cottage

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chestertown hotels

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

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

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

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.

1. Pine Tree Motel & Cabins

Chestertown

Pingfei

RM712

RM791 total

includes taxes & fees

12 Sept - 13 Sept

2. Friends Lake Inn

Chestertown

Jessica

RM398

RM442 total

includes taxes & fees

22 Sept - 23 Sept

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

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

3. The Fern Lodge

Chestertown

robert

RM1,632

RM1,811 total

includes taxes & fees

13 Sept - 14 Sept

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 room with a wooden bench, a table, and chairs. There is a map on the wall and a window with a curtain.

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

4. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

Andrew

RM304

RM338 total

includes taxes & fees

13 Sept - 14 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 self-service beverage station with a refrigerator, microwave, and coffee maker.

A hotel room with a bed, a desk with a chair, a television, a lamp, and a framed picture on the wall.

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

5. Spark by Hilton Lake George Outlets

Lake George

Maria

RM430

RM478 total

includes taxes & fees

16 Sept - 17 Sept

A large, historic hotel with multiple buildings, a well-maintained lawn, and a mountainous backdrop.

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

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

A lifeguard tower with a ladder and a bag of life-saving equipment.

6. Silver Bay YMCA Inn and Conference Center

Silver Bay

Marina

RM778

RM864 total

includes taxes & fees

13 Sept - 14 Sept

A lakeside cabin with a wooden deck and a view of the lake.

A lakeside hotel with a dock, lounge chairs, and a view of autumn trees.

A log cabin with a balcony and a stone foundation.

A waterfront property with docked boats, a wooden fence, and a sign reading "Grout House."

7. Trout House Village Resort

Hague

Matthew

RM541

RM702 total

includes taxes & fees

13 Sept - 14 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 spacious lobby with a Christmas tree, seating area, and a spiral staircase.

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

8. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Paul

RM377

RM419 total

includes taxes & fees

13 Sept - 14 Sept

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

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

9. Hampton Inn & Suites Lake George

Lake George

Jose

RM531

RM589 total

includes taxes & fees

27 Sept - 28 Sept

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

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

A dining room with a round table set for four, featuring white tablecloths, black napkins, and silverware.

10. The Queensbury Hotel

Glens Falls

nicole

RM484

RM538 total

includes taxes & fees

13 Sept - 14 Sept

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

A Fairfield Inn & Suites hotel with a modern exterior, a stone pillar, and a well-lit entrance.

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.

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

Queensbury

Denise

RM498

RM553 total

includes taxes & fees

20 Sept - 21 Sept

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.

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

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

12. Comfort Inn & Suites Lake George

Lake George

Deborah

RM478

RM530 total

includes taxes & fees

13 Sept - 14 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 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 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.

13. Courtyard by Marriott Lake George

Lake George

Yasmeen

RM602

RM669 total

includes taxes & fees

23 Sept - 24 Sept

A hotel room with two beds, a desk with a computer and a television, a microwave, and a dresser.

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.

14. Point Hotel Queensbury

Queensbury

David

RM402

RM446 total

includes taxes & fees

14 Sept - 15 Sept

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

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.

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

15. Depe Dene Lakeside Resort

Lake George

Melissa

RM337

RM374 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 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.

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

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

Queensbury

KELLY

RM406

RM451 total

includes taxes & fees

14 Sept - 15 Sept

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

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.

A restaurant with tables and chairs, large windows with a view of a beach and mountains, and a carpeted floor.

17. The Georgian Lakeside Resort

Lake George

cait

RM444

RM492 total

includes taxes & fees

14 Sept - 15 Sept

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

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

Heather

RM374

RM415 total

includes taxes & fees

15 Sept - 16 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 spacious kitchen with a central island, a chandelier, and a ceiling fan.

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

19. Quality Inn Lake George

Lake George

David

RM513

RM569 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

20. Admiral Motel

Lake George

Grayson

RM299

RM332 total

includes taxes & fees

17 Sept - 18 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"Great location. Friendly staff. Great breakfast"

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

8/10 Good

"Great place to stop on my way to Canada. Staaf at front desk was very inviting. Place was quiet and safe for a single traveler. Rooms are older but well kept. Breakfast was good just missing some fresh fruit. Price was very affordable."

Depe Dene Lakeside Resort

10/10 Excellent

"Great spot. Staff are amazing. I really felt welcome there."

Lakefront Terrace Resort

10/10 Excellent

"It was wonderful clean great beach absolutely wonderful. Just wish others not from here would respect rules manors others around them . Clean up after them selves try to not get stuff for free . Watch there kids not have kids watch kids .Would definitely go back ."

Lodge at Schroon Lake

10/10 Excellent

"Very friendly staff"

Howard Johnson by Wyndham Lake George

10/10 Excellent

"Will stay again"

Great Escape Lodge & Indoor Waterpark

10/10 Excellent

"good place to be"

Pine Tree Motel & Cabins

10/10 Excellent

"Comfy, cozy with a wonderful staff and a fantastic location! Rooms are clean and comfortable. Has free wifi and is strategically located - easy to get anywhere!"

Super 8 by Wyndham Lake George/Warrensburg Area

8/10 Good

"I LIKED MY STAY FOR 2 NIGHTS. IT WAS RELAXING. AFTER THE FIRST NIGHT AND UPON MY RETURN FROM SIGHTSEEING, MY REMAIN WAS NOT CLEANED . LACK OF HOUSE KEEPING PUT ME OFF"

More cheap stays in Chestertown

Howard Johnson by Wyndham Lake George

99 Canada St Lake George NY

RM269

RM298 total

4 Oct - 5 Oct

includes taxes & fees

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

RM300

RM333 total

13 Sept - 14 Sept

includes taxes & fees

Super 8 by Wyndham Lake George/Warrensburg Area

3619 State Route 9 Lake George NY

RM304

RM338 total

13 Sept - 14 Sept

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY

RM333

RM383 total

20 Sept - 21 Sept

includes taxes & fees

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY

RM430

RM478 total

16 Sept - 17 Sept

includes taxes & fees

The Georgian Lakeside Resort

384 Canada Street Lake George NY

RM444

RM492 total

14 Sept - 15 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 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. Provides daily, an indoor pool and free self parking. Holiday Inn Resort Lake George - Adirondack Area by IHG and The Georgian Lakeside Resort 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.

Chestertown hotels from RM298

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. Super 8 by Wyndham Lake George/Warrensburg Area

5. Spark by Hilton Lake George Outlets

6. Silver Bay YMCA Inn and Conference Center

7. Trout House Village Resort

8. La Quinta Inn & Suites by Wyndham Lake George

9. Hampton Inn & Suites Lake George

10. The Queensbury Hotel

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

12. Comfort Inn & Suites Lake George

13. Courtyard by Marriott Lake George

14. Point Hotel Queensbury

15. Depe Dene Lakeside Resort

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

17. The Georgian Lakeside Resort

18. The Juliana Resort

19. Quality Inn Lake George

20. Admiral Motel

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

La Quinta Inn & Suites by Wyndham Lake George

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

Depe Dene Lakeside Resort

Lakefront Terrace Resort

Lodge at Schroon Lake

Howard Johnson by Wyndham Lake George

Great Escape Lodge & Indoor Waterpark

Pine Tree Motel & Cabins

Super 8 by Wyndham Lake George/Warrensburg Area

More cheap stays in Chestertown

Howard Johnson by Wyndham Lake George

Baymont by Wyndham Queensbury / Lake George

Super 8 by Wyndham Lake George/Warrensburg Area

Adirondack Retreat Inn & Suites

Spark by Hilton Lake George Outlets

The Georgian Lakeside Resort

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app