Hotels in Chestertown

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Where to stay in Chestertown?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Chestertown on Hotels.com. These Chestertown hotels consistently deliver on quality, location and traveler experience. Last updated on October 3, 2026.

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

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

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

CNY1,174

CNY1,303 total

includes taxes & fees

Oct 4 - Oct 5

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

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

2. The Fern Lodge

Chestertown

CNY2,689

CNY2,985 total

includes taxes & fees

Oct 4 - Oct 5

3. Friends Lake Inn

Chestertown

CNY866

CNY962 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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

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

4. Comfort Inn & Suites Lake George

Lake George

CNY665

CNY738 total

includes taxes & fees

Oct 7 - Oct 8

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

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

5. Courtyard by Marriott Lake George

Lake George

CNY932

CNY1,035 total

includes taxes & fees

Oct 19 - Oct 20

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

A log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.

6. Lodge at Schroon Lake

Schroon Lake

CNY929

CNY1,270 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

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

7. Spark by Hilton Lake George Outlets

Lake George

CNY734

CNY815 total

includes taxes & fees

Oct 8 - Oct 9

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

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.

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

CNY564

CNY626 total

includes taxes & fees

Oct 28 - Oct 29

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

A hotel lobby with a reception desk, seating area, stone fireplace, and large windows.

A spacious living area with a stone fireplace, comfortable seating, a large window with a view, and a chandelier.

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

Lake George

CNY838

CNY931 total

includes taxes & fees

Oct 25 - Oct 26

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 wooden-framed bed with a plaid blanket, a headboard with antlers, and a mounted picture.

10. The Alpine Lodge

North Creek

CNY840

CNY1,004 total

includes taxes & fees

Oct 27 - Oct 28

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 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.

11. Quality Inn Lake George

Lake George

CNY741

CNY822 total

includes taxes & fees

Nov 3 - Nov 4

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 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.

12. Hampton Inn & Suites Lake George

Lake George

CNY678

CNY753 total

includes taxes & fees

Oct 29 - Oct 30

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

A wooden deck with white railings leading to a lakeside view.

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.

13. Depe Dene Lakeside Resort

Lake George

CNY598

CNY663 total

includes taxes & fees

Oct 4 - Oct 5

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 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.

14. Super 8 by Wyndham Lake George/Warrensburg Area

Lake George

CNY467

CNY519 total

includes taxes & fees

Oct 5 - Oct 6

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

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

Queensbury

CNY530

CNY588 total

includes taxes & fees

Nov 1 - Nov 2

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

A terrace with outdoor seating, a view of a lake, and a dock.

16. Lodges At Cresthaven

Lake George

CNY1,301

CNY1,445 total

includes taxes & fees

Oct 19 - Oct 20

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

A bar area with wooden windows, shelves of liquor bottles, and glasses.

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.

17. Gore Mountain Lodge

North Creek

CNY899

CNY998 total

includes taxes & fees

Oct 20 - Oct 21

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

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.

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

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

Queensbury

CNY694

CNY771 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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.

19. The Georgian Lakeside Resort

Lake George

CNY731

CNY811 total

includes taxes & fees

Oct 4 - Oct 5

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

A cozy room with a large bed, a fireplace, a stone wall, and wooden beams on the ceiling.

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.

20. Adirondack Retreat Inn & Suites

Lake George

CNY658

CNY757 total

includes taxes & fees

Oct 5 - Oct 6

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Go beyond your typical stay in Chestertown

Pet friendly

Apartment

Pool

Family friendly

Hot tub

Cottage

Our prices for hotels in Chestertown are cheapest in March

Top neighborhoods in Chestertown

Chester Shores

Chester Shores

Chestertown's Chester Shores neighborhood offers attractions including Loon Lake.

See properties

Top landmarks in Chestertown

Loon Lake

8.8/10 (8 reviews)

Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay.

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Friends Lake

9.4/10 (14 reviews)

Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay.

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Loon Lake Beach

8.4/10 (7 reviews)

If you can't wait to get to the beach, you might enjoy a trip to Loon Lake Beach located 2 mi (3.3 km) from central Chestertown.

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Tripp Pond

8.6/10 (4 reviews)

Tripp Pond is 3.9 mi (6.3 km) from central Chestertown, why not stop by during your stay.

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Learn more about Chestertown

Chestertown is well-known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.

See all hotels in Chestertown

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

Check out reviews of Chestertown hotels guests love

Depe Dene Lakeside Resort

10/10 Excellent

"Laurie, and Hansen were absolutely amazing! I called several times and everyone was so helpful! I would 100% recommend this this resort!"

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

8/10 Good

"Our stay was basically good. The location was perfect for our needs. Lots of things to do and see. Our room was comfortable as was the bed. Cleaning was a bit random and incomplete. Mainly dumped trash and partially made the bed. We did get clean towels. We would stay again but would suggest an little improvement in that area."

Fort William Henry Hotel and Conference Center

10/10 Excellent

"Great staff and location!"

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"Clean and well maintained property"

Holiday Inn Resort Lake George - Adirondack Area by IHG

8/10 Good

"Parking easygoing"

Hampton Inn & Suites Lake George

10/10 Excellent

"Great place to stay."

Lodge at Schroon Lake

10/10 Excellent

"What a beautiful spot! The property is well maintained and the staff are helpful and friendly. The grounds offer so many options for fun activities, and there are no additional fees to guests to use them! The evening fire pits and smores were a nice touch. We definitely plan to return!"

Nordick's Inn

8/10 Good

"Parking facile, gens très gentil, près du lac, très belle ville pour des vacances d’été, plusieurs restaurants à proximité"

Lakefront Terrace Resort

8/10 Good

"We had a nice and relaxing stay."

Frequently asked questions

How much does a hotel room cost in Chestertown?

You can find top hotels in Chestertown from CNY476 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".

How can I find deals and earn rewards at Chestertown hotels?

Discover great deals on Chestertown hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. And make sure to check out our last-minute deals on Chestertown hotels.

Can I book Chestertown hotels with free cancellation?

In order to book a refundable Chestertown hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some of the best hotels in Chestertown for couples?

Stay at a top-rated Chestertown romantic hotel and make the most of your couple's vacation. Our travelers love Friends Lake Inn, a hotel with a restaurant as well as in-room champagne service. Another romantic hotel with top reviews is The Fern Lodge. This bed & breakfast offers a private hot tub and an in-room fireplace for a perfect stay. Discover more hotels in Chestertown on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".

What are some of the best Chestertown hotels with free parking?

If you're driving, a great Chestertown hotel with free parking is a bonus. Our travelers' favorites include:

The Fern Lodge: A bed & breakfast with an average guest rating of 9.8 out of 10
Friends Lake Inn: A hotel with an average guest rating of 8.8

What are some popular hotels in central Chestertown?

If you're looking for hotels in central Chestertown, check out Friends Lake Inn. Travelers love Friends Lake Inn for its location, as well as the restaurant, bar/lounge and proposal/romance packages this hotel offers. Chester Shores is a central neighborhood for your Chestertown vacation.

What accommodations do travelers like in Chestertown?

Guests like Pine Tree Motel & Cabins.

Can I book a refundable accommodation in Chestertown?

If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Chestertown if I want a vacation home instead of a hotel?

If you're looking for a good alternative to a hotel, look over our selection of 62 vacation homes. You can also consider one of the 5 apartments or 19 cottages.

What will the weather in Chestertown be like during my visit?

The warmest months in Chestertown are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 25°F. The rainiest months are June and July.

Why should I book my Chestertown hotel with Hotels.com?

There are plenty of reasons to book your Chestertown travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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Book Hotels in Chestertown on Hotels.com

Hotels in Chestertown

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Chestertown?

1. Pine Tree Motel & Cabins

2. The Fern Lodge

3. Friends Lake Inn

4. Comfort Inn & Suites Lake George

5. Courtyard by Marriott Lake George

6. Lodge at Schroon Lake

7. Spark by Hilton Lake George Outlets

8. La Quinta Inn & Suites by Wyndham Lake George

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

10. The Alpine Lodge

11. Quality Inn Lake George

12. Hampton Inn & Suites Lake George

13. Depe Dene Lakeside Resort

14. Super 8 by Wyndham Lake George/Warrensburg Area

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

16. Lodges At Cresthaven

17. Gore Mountain Lodge

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

19. The Georgian Lakeside Resort

20. Adirondack Retreat Inn & Suites

Go beyond your typical stay in Chestertown

Price trends for hotels in Chestertown

Typical weather for Chestertown

Top neighborhoods in Chestertown

Chester Shores

Top landmarks in Chestertown

Loon Lake

Friends Lake

Loon Lake Beach

Tripp Pond

Learn more about Chestertown

Check out reviews of Chestertown hotels guests love

Depe Dene Lakeside Resort

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

Fort William Henry Hotel and Conference Center

La Quinta Inn & Suites by Wyndham Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

Hampton Inn & Suites Lake George

Lodge at Schroon Lake

Nordick's Inn

Lakefront Terrace Resort

Frequently asked questions

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