Chestertown Hotels from €58 - 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

Cabin

Pool

Apartment

Cottage

Family friendly

Waterpark

Castle

Condo

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Chestertown hotels

1. Friends Lake Inn

Chestertown

Michael

€102

includes taxes & fees

13 Oct - 14 Oct

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

2. Pine Tree Motel & Cabins

Chestertown

John

€173

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

3. The Fern Lodge

Chestertown

robert

€397

includes taxes & fees

15 Oct - 16 Oct

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

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

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

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

4. The Juliana Resort

Diamond Point

Julia

€108

includes taxes & fees

12 Oct - 13 Oct

A hotel room with a bed, bedside tables, a desk, a chair, a television, and a painting on the wall.

A breakfast area with tables, chairs, a juice bar, and a refrigerator with food items.

A hotel with a swimming pool, parking lot, and a view of a lake and mountains.

A swimming pool with white lounge chairs and a blue umbrella.

5. Skyline Hotel Lake George

Lake George

Alessandro

€72

includes taxes & fees

19 Oct - 20 Oct

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

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.

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

6. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

James

€70

includes taxes & fees

15 Oct - 16 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 modern building with a parking lot and a fenced area.

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

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

7. Spark by Hilton Lake George Outlets

Lake George

Julie Van

€77

includes taxes & fees

1 Nov - 2 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 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.

8. The Alpine Lodge

North Creek

Richard

€134

includes taxes & fees

27 Oct - 28 Oct

A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

A white public house with a prominent bell tower, a large arched window, and a sign indicating its location in North Creek.

A modern restaurant with a central bar, dining area with tables and chairs, and large windows with arched tops.

9. Public House

North Creek

Cara

€151

includes taxes & fees

25 Oct - 26 Oct

A wooden lodge with a metal roof, a covered porch, and a sign that reads "Becks."

A rustic interior with wooden beams, a large window, and multiple tables and chairs.

A yurt interior with a central wood-burning stove, leather seating, and a traditional rug.

A lodge sign with a mountain graphic, surrounded by greenery and two yellow chairs.

10. Gore Mountain Lodge

North Creek

Jennifer

€133

includes taxes & fees

20 Oct - 21 Oct

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

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

11. Depe Dene Lakeside Resort

Lake George

Jessica

€97

includes taxes & fees

12 Oct - 13 Oct

An indoor swimming pool with a glass ceiling, clear pool water, and a few chairs along the side.

A building with a covered porch, white doors, and a row of white plastic chairs.

A compact hotel room with a kitchenette, a dining area, a bed, and a TV.

A hotel room with two beds, a balcony, and a view of neighboring houses.

12. Adirondack Retreat Inn & Suites

Lake George

Joseph

€101

includes taxes & fees

11 Oct - 12 Oct

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

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.

A spacious lobby with a stone fireplace, blue seating, and a large chandelier.

13. Hampton Inn & Suites Lake George

Lake George

PATRICIA

€100

includes taxes & fees

29 Oct - 30 Oct

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

A table with a meal, a drink, and a view of the sea.

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

A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.

14. The Georgian Lakeside Resort

Lake George

cait

€108

includes taxes & fees

11 Oct - 12 Oct

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

A hotel pool area with lounge chairs and umbrellas, a clear sky, and a building with multiple windows.

15. Comfort Inn & Suites Lake George

Lake George

Deborah

€100

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

16. Quality Inn Lake George

Lake George

Stephanie

€109

includes taxes & fees

8 Nov - 9 Nov

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 modern lounge area with a round table, chairs, a fireplace, and a television mounted on a textured wall.

17. Courtyard by Marriott Lake George

Lake George

SANDRA

€123

includes taxes & fees

8 Nov - 9 Nov

A wooden deck with Adirondack chairs facing a calm lake and distant mountains.

A beachside seating area with a fire pit surrounded by chairs and red umbrellas, overlooking a lake with mountains in the background.

A log cabin-style building with a metal roof, stone pillars, and a glass door entrance.

A hotel with a pool, beach chairs, umbrellas, and a view of the lake.

18. Scotty's Lakeside Resort

Lake George

Judy

€98

includes taxes & fees

12 Oct - 13 Oct

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 Christmas tree, seating area, and a spiral staircase.

19. La Quinta Inn & Suites by Wyndham Lake George

Lake George

Robert

€83

includes taxes & fees

1 Nov - 2 Nov

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

A coffee station with two espresso machines, a coffee dispenser, and a tray of disposable cups.

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

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

20. Howard Johnson by Wyndham Lake George

Lake George

Maia

€74

includes taxes & fees

12 Oct - 13 Oct

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

Baymont by Wyndham Queensbury / Lake George

8/10 Good

"Breakfast wasn’t very good"

Friends Lake Inn

8/10 Good

"The staff were very helpful and friendly. The amenities should be improved and the bathroom shower and tiles should be cleaner."

Fort William Henry Hotel and Conference Center

10/10 Excellent

"Side building are motel style with stairs, thin walls, carpet has moisture smell, otherwise clean rooms, plenty of parking."

Surfside On The Lake

8/10 Good

"Stayed here during a wedding weekend. The room was a little dated, but was clean and had the essential amenities for our stay. We arrived early and were allowed to check in as soon as we arrived (four hours ahead of the official check in time)."

Great Escape Lodge & Indoor Waterpark

8/10 Good

"Great value in the area to be honest. Great price compared to other options in the area. Very convenient location to Lake George and the Worlds Biggest Garage Sale."

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good

"This property is very well-maintained and clean. Their rooms are fresh and updated and the property looks relaxing and inviting. We didn’t really use any of the amenities, but it was well situated. The only thing I would say is if you’re looking for something on the water or with water views, this is not the property for you. Other than that, it’s well worth a visit."

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

10/10 Excellent

"We really enjoyed our stay here. The room was very clean and comfortable with some updates. The carpet in the main hallways could do with updating. The breakfast was delicious with several options. Snacks and a bottle of water were given free as extras. In all it was a good location for a variety of restaurants and shopping, and to visit Lake George."

The Georgian Lakeside Resort

8/10 Good

"Room was sparkling clean but the smell of the cleaning chemicals vas very strong in the air that gave us both headache. Even after airing the room, the smell lingered around."

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY

€58

1 Nov - 2 Nov

includes taxes & fees

5.4/10 (1,002 reviews)

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY

€75

12 Oct - 13 Oct

includes taxes & fees

7.6/10 Good! (1,123 reviews)

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY

€77

1 Nov - 2 Nov

includes taxes & fees

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY

€101

11 Oct - 12 Oct

includes taxes & fees

The Georgian Lakeside Resort

384 Canada Street Lake George NY

€108

11 Oct - 12 Oct

includes taxes & fees

8.6/10 Excellent! (1,005 reviews)

Surfside On The Lake

400 Canada Street Lake George NY

€113

12 Oct - 13 Oct

includes taxes & fees

8/10 Very good! (849 reviews)

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.

What are some of the best holiday rentals that Chestertown has to offer?

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: This highly rated holiday home rental in Chestertown is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Eagles Nest at Loon Lake near Gore Mountain as a favourite home for rent in Chestertown. See all 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. Other good options for you and your pet's trip include Waterfront 1860s Farmhouse, Private Hot Tub, Fire Pit, Pond, Canoe, Walk to Town and Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing. 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. Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool. and The Georgian Lakeside Resort are two additional hotels that offer an on-site pool. View all hotels with pools in Chestertown.

What's the top hotel in Chestertown with an on-site water park or a water park nearby?

1970s acreage surrounded by trees with deck, grill, & internet is a favourite water park hotel 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

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. Friends Lake Inn

2. Pine Tree Motel & Cabins

3. The Fern Lodge

4. The Juliana Resort

5. Skyline Hotel Lake George

6. Super 8 by Wyndham Lake George/Warrensburg Area

7. Spark by Hilton Lake George Outlets

8. The Alpine Lodge

9. Public House

10. Gore Mountain Lodge

11. Depe Dene Lakeside Resort

12. Adirondack Retreat Inn & Suites

13. Hampton Inn & Suites Lake George

14. The Georgian Lakeside Resort

15. Comfort Inn & Suites Lake George

16. Quality Inn Lake George

17. Courtyard by Marriott Lake George

18. Scotty's Lakeside Resort

19. La Quinta Inn & Suites by Wyndham Lake George

20. Howard Johnson by Wyndham 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

Friends Lake Inn

Fort William Henry Hotel and Conference Center

Surfside On The Lake

Great Escape Lodge & Indoor Waterpark

Holiday Inn Resort Lake George - Adirondack Area by IHG

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

The Georgian 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

Explore a world of travel with Expedia

Go further with the Expedia app