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

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Our top choices for Chestertown hotels

An indoor water park with multiple pools, slides, and a high platform.
A cozy lobby with a fireplace, Christmas trees, and a seating area with a sofa and chairs.
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.

1. Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark
Queensbury
Guest highlights
  • Very clean pool area
  • Steps from the water park entrance
  • Excellent quality food options available
$115 nightly
$128 total
Oct 12 - Oct 13
Total with taxes and fees
Great Escape Lodge & Indoor Waterpark
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 room with a large bathtub, a bed with white bedding, a dark headboard, and a black and white patterned floor.
A hotel with a prominent 'LAQUINTA' sign, a covered entrance, and a parking lot.

2. La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
Lake George
Guest highlights
  • Large pool and hot tub
  • Free continental breakfast each morning
  • Ample parking spaces available on-site
$84 nightly
$93 total
Oct 18 - Oct 19
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Lake George
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 arbor structure in a grassy area with two potted plants.

3. Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
Chestertown
Guest highlights
  • Located near Chestertown
  • Fresh coffee provided every morning
  • Great choice for families with kids
$175 nightly
$194 total
Sep 26 - Sep 27
Total with taxes and fees
Pine Tree Motel & Cabins
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 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.

4. The Georgian Lakeside Resort

The Georgian Lakeside Resort
Lake George
Guest highlights
  • Nice pool with bar service
  • Excellent on-site restaurant and bar
  • Beautiful view from the room
$97 nightly
$108 total
Sep 27 - Sep 28
Total with taxes and fees
The Georgian Lakeside Resort
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 large, multi-story log cabin with a prominent chimney, surrounded by dense forest and rocky terrain.
A cozy room with a stone fireplace, a comfortable sofa, and a table with books and snacks.

5. The Fern Lodge

The Fern Lodge
Chestertown
Guest highlights
  • Peaceful and away from the noise
  • Beautiful views from the property
  • Complimentary breakfasts each morning
$490 nightly
$544 total
Oct 4 - Oct 5
Total with taxes and fees
The Fern Lodge

6. Friends Lake Inn

Friends Lake Inn
Chestertown
Guest highlights
  • Very good on-site restaurant
  • Consistent daily housekeeping service
  • Included breakfast options available
$122 nightly
$135 total
Sep 28 - Sep 29
Total with taxes and fees
Friends Lake Inn
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 hotel room with two beds, a balcony, and a view of neighboring houses.
A compact hotel room with a kitchenette, a dining area, a bed, and a TV.

7. Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites
Lake George
Guest highlights
  • Playground for younger guests
  • Well-kept on-site pool area
  • Free and sufficient parking available
$93 nightly
$103 total
Sep 27 - Sep 28
Total with taxes and fees
Adirondack Retreat Inn & Suites
A hotel room with two beds, a map on the wall, and a door.
A dining room with a round table set for four, featuring white tablecloths, black napkins, and silverware.
A sign for 'The Queensbury' with a large 'Q' logo, indicating a venue for meetings, conferences, weddings, and banquets.
A gym with various weightlifting equipment, including dumbbells and a bench.

8. The Queensbury Hotel

The Queensbury Hotel
Glens Falls
Guest highlights
  • Pool and hot tub
  • Ample on-site parking space
  • Excellent on-site restaurant
$124 nightly
$138 total
Oct 12 - Oct 13
Total with taxes and fees
The Queensbury Hotel
A cozy log cabin interior with a stone fireplace, wooden ceiling, and a large arched window.
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.
A stone fireplace with a wooden mantel, surrounded by a wooden gazebo with a triangular roof, and a stone pathway leading to it.

9. The Alpine Lodge

The Alpine Lodge
North Creek
Guest highlights
  • High-end granola bars available
  • Easy parking for arriving guests
  • Rooms with a king bed
$137 nightly
$152 total
Sep 27 - Sep 28
Total with taxes and fees
The Alpine Lodge
A restaurant with round tables and wicker chairs, wooden beams on the ceiling, and hanging light fixtures.
A stone sculpture, a row of white lounge chairs, and lush greenery.
A modern building with a unique triangular architectural design, featuring multiple levels and a well-maintained garden area with trimmed bushes and a palm tree.
A fountain in a landscaped area with a stone wall, a building with a sloped roof, and trees in the background.

10. Tiki Resort

Tiki Resort
Lake George
Guest highlights
  • Great choice for families with kids
  • Very good food quality at restaurant
  • Parking on-site for guests
$67 nightly
$74 total
Sep 27 - Sep 28
Total with taxes and fees
Tiki Resort
A row of cabins with balconies, a well-maintained lawn, and a lake view.
A lakeside property with docked boats, a stone pathway, and a view of the surrounding forest and buildings.
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 log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.

11. Lodge at Schroon Lake

Lodge at Schroon Lake
Schroon Lake
Guest highlights
  • Lake views from the rooms
  • Large pool and hot tub
  • Delicious food and dining on offer
$169 nightly
$191 total
Oct 26 - Oct 27
Total with taxes and fees
Lodge at Schroon Lake

12. Lakefront Terrace Resort

Lakefront Terrace Resort
Lake George
Guest highlights
  • Swimming pool available on site
  • Ample parking on the property
  • Spectacular views from the property
$74 nightly
$82 total
Oct 6 - Oct 7
Total with taxes and fees
Lakefront Terrace Resort
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 with a covered entrance, large windows, and a parking lot.
A spacious living area with a stone fireplace, comfortable seating, a large window with a view, and a chandelier.

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

Holiday Inn Resort Lake George - Adirondack Area by IHG
Lake George
Guest highlights
  • Pool with family-friendly amenities
  • Ample free parking available on-site
  • On-site restaurant with delicious food
$125 nightly
$139 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Resort Lake George - Adirondack Area by IHG
A wooden deck with Adirondack chairs facing a calm lake and distant mountains.
A log cabin-style building with a metal roof, stone pillars, and a glass door entrance.
A beachside seating area with a fire pit surrounded by chairs and red umbrellas, overlooking a lake with mountains in the background.
A lakeside beach with rows of beach chairs and a dock with boats.

14. Scotty's Lakeside Resort

Scotty's Lakeside Resort
Lake George
Guest highlights
  • Beautiful swimming pool with fire pits
  • Scenic lakeside property with great views
  • Beautiful beach location nearby
$99 nightly
$110 total
Sep 27 - Sep 28
Total with taxes and fees
Scotty's Lakeside Resort
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 lobby with a reception desk, seating area, staircase, and fireplace.

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

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Queensbury
Guest highlights
  • Clean and nice pool area
  • Great breakfast buffet options
  • Plenty of available parking
$92 nightly
$102 total
Oct 18 - Oct 19
Total with taxes and fees
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
An outdoor dining area with a fire feature, surrounded by white furniture and a gazebo.
A river with a large white boat docked at a pier, surrounded by autumn-colored trees and buildings in the background.
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.

16. Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center
Lake George
Guest highlights
  • Beautiful area with gardens
  • Excellent on-site dining options
  • Beautiful swimming pool for guests
$121 nightly
$134 total
Oct 14 - Oct 15
Total with taxes and fees
Fort William Henry Hotel and Conference Center
A hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.
An indoor swimming pool with clear water, red safety flooring, and lounge chairs along the wall.
A hotel lobby with leather sofas, a reception desk, a television, and a sign for 'Baymont.'
A conference room with rows of tables, chairs, and a podium.

17. Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George
Queensbury
Guest highlights
  • Great choice for families with kids
  • Included breakfast with waffles and eggs
  • Hassle-free parking available
$74 nightly
$82 total
Sep 27 - Sep 28
Total with taxes and fees
Baymont by Wyndham Queensbury / Lake George
An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.
A snow-covered lodge with cabins, a clear view of a lake, and mountains in the background.
A lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.
A wooden cabin interior with a kitchen featuring a stainless steel refrigerator, wooden cabinets, and a bar area with stools.

18. Lodges At Cresthaven

Lodges At Cresthaven
Lake George
Guest highlights
  • Balcony overlooking lake George
  • Beautiful swimming pool for guests
  • Convenient on-site parking available
$213 nightly
$236 total
Oct 19 - Oct 20
Total with taxes and fees
Lodges At Cresthaven
A wooden lodge with a metal roof, a covered porch, and a sign that reads "Becks."
A lodge sign with a mountain graphic, surrounded by greenery and two yellow chairs.
A rustic interior with wooden beams, a large window, and multiple tables and chairs.
A bar area with wooden windows, shelves of liquor bottles, and glasses.

19. Gore Mountain Lodge

Gore Mountain Lodge
North Creek
Guest highlights
  • On-site restaurant serving German cuisine
  • Roomy, generously sized rooms
$149 nightly
$165 total
Sep 27 - Sep 28
Total with taxes and fees
Gore Mountain Lodge
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 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.

20. Depe Dene Lakeside Resort

Depe Dene Lakeside Resort
Lake George
Guest highlights
  • Swimming pool open to guests
  • Friendly and accommodating front desk staff
  • Scenic lake view from rooms
$109 nightly
$121 total
Sep 27 - Sep 28
Total with taxes and fees
Depe Dene Lakeside Resort
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Where to stay in and around Chestertown

Chestertown, a charming town in New York, is perfect for outdoor enthusiasts and romantic getaways. Enjoy serene scenery, family vacations, and adventure activities nearby. Explore the best upstate New York getaways for a relaxing escape, making it an ideal choice for unforgettable New York weekend getaways.
An aerial view of a small island with dense forests, a large white mansion, and a dock with boats.
A lakeside community with a marina, boats, and surrounding forested hills.
A lakeside community with houses, roads, and a forested area.
An aerial view of a lakeside resort with a large house, a swimming pool, and a dock.
A calm lake with a reflection of the sky and surrounding landscape, including trees and distant mountains.
Photo by Michelle Rapier

Bolton Landing

Discover Bolton Landing, a charming destination perfect for outdoor enthusiasts and families seeking a memorable getaway. This picturesque area offers stunning views of Lake George, a tranquil beach, and the historic Bolton Historical Museum, making it ideal for those who appreciate nature and romance. Just about 10 miles by car from Chestertown, Bolton Landing provides easy access to attractions like The Sagamore Golf Club, ensuring a delightful stay. It's a smart choice for your next vacation!

A lake surrounded by forested hills with autumn foliage.
A calm lake with a forested hill in the background and a small house near the water's edge.
Photo by Rick Tuers
A rustic metal sculpture resembling a deer in a grassy area with trees in the background.
Photo by Rick Tuers

Brant Lake

Plan your stay in Brant Lake, a top-rated choice for families and adventure seekers looking for a scenic escape. This picturesque area offers endless opportunities to explore nature, from the stunning shores of Lake George to the serene Loon Lake Beach. For those who enjoy winter sports, nearby ski resorts provide thrilling experiences. Located about 3 miles by car from Chestertown, Brant Lake is an ideal base for your vacation, combining outdoor fun with beautiful landscapes.

Chester Shores

If you are an outdoor enthusiast or a family looking for a scenic getaway, Chester Shores is an ideal choice, known for its breathtaking landscapes and romantic atmosphere. Just around Chestertown, you'll find beautiful spots like Loon Lake Beach and Friends Lake, perfect for summer activities, while the Natural Stone Bridge and Caves offer unique exploration year-round. With its seasonal charm peaking from July to September, Chester Shores is a smart hotel booking choice for an unforgettable vacation experience.

A forest with autumn foliage in shades of orange, yellow, and green.
A forested landscape with a lake and distant mountains under a cloudy sky.

Pottersville

Pottersville stands out as a prime spot for family-oriented travelers seeking a nature-filled weekend getaway. Nestled near stunning attractions like Schroon Lake, the Natural Stone Bridge and Caves, and Loon Lake Beach, visitors can immerse themselves in outdoor adventures year-round. With its vibrant scenery and recreational options, Pottersville makes for an ideal escape. Located about 5 miles by car from Chestertown, it’s a smart choice for those looking to enjoy a picturesque retreat.

A mountainous landscape with autumn foliage, houses, and a river.
A calm lake surrounded by dense forests and mountains.
A river winding through a forest with a mountain in the background.
A lakeside village with colorful autumn foliage and houses with distinct architectural styles.
A mountainous landscape with dense forests and a clear sky.

Adirondack

Travelers seeking adventure and a connection with nature will find Adirondack to be the ideal base for their vacation, featuring breathtaking landscapes and outdoor activities. With attractions like the scenic Schroon Lake, the intriguing Natural Stone Bridge and Caves, and the tranquil Pharaoh Lake Wilderness, visitors can immerse themselves in the beauty of the area. Located about 8 miles by car from Chestertown, Adirondack offers a smart choice for lodging, ensuring a memorable stay surrounded by nature’s wonders.

Stay near popular attractions in and around Chestertown

Escape to Chestertown, where outdoor adventures, stunning scenery, and romantic getaways await. With nearby attractions like beautiful lakes, serene beaches, and charming resorts, you'll find the perfect backdrop for relaxation and exploration in this picturesque destination. Enjoy nature's beauty and make unforgettable memories!

Loon Lake

8.8/10 (8 reviews)
Ideal for travelers interested in serene outdoor escapes, Loon Lake in Chestertown offers stunning scenery and romantic beach vibes. Enjoy peaceful moments by the water or explore the surrounding natural beauty. Conveniently located within Chestertown, this picturesque lake is a perfect base for your Adirondack adventure.
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Friends Lake

9.4/10 (14 reviews)
Experience the best of outdoor romance at Friends Lake, a picturesque destination in Chestertown, New York. Enjoy stunning scenery and tranquil beach vibes while immersing yourself in nature's beauty. Located within Chestertown, Friends Lake offers convenient access to a serene getaway, making it an ideal spot for your vacation.
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The Sagamore Golf Club

Ideal for golf lovers, The Sagamore Golf Club offers a stunning lakeside course that combines natural beauty with challenging play. Located about 8 miles by car from Chestertown, it provides easy access for a memorable day of relaxation and recreation, making it a great option for your vacation.
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Loon Lake Beach

8.4/10 (7 reviews)
No trip is complete without a visit to Loon Lake Beach, a delightful spot for families looking to enjoy sunny beach vibes. Nestled within Chestertown, this picturesque beach offers a serene escape for swimming and relaxation. Staying nearby makes it easy to soak up the sun and explore all that the area has to offer.
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Natural Stone Bridge and Caves

6.8/10 (3 reviews)
An essential stop for outdoor adventurers, Natural Stone Bridge and Caves offers a unique experience with stunning geological formations and exciting cave exploration. Located about 10 miles by car from Chestertown, it’s a convenient getaway for those looking to immerse themselves in nature’s wonders.
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Tripp Pond

8.6/10 (4 reviews)
For nature lovers seeking a serene getaway, Tripp Pond offers a picturesque escape in Chestertown. This scenic lake is perfect for outdoor activities and romantic strolls along its shores. Easily accessible within the town, Tripp Pond makes for a convenient and tranquil spot to unwind during your visit.
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Pack Demonstration Forest

Perfectly suited for outdoor lovers, Pack Demonstration Forest offers an immersive experience in nature with its adventure vibes. Located about 11 miles by car from Chestertown, it’s an easy trip for those looking to explore the beauty of the forest. Staying nearby allows for convenient access to this natural gem.
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Blue Line Outdoor Center

A must-see for outdoor adventurers, Blue Line Outdoor Center offers a relaxing and trendy escape in Wevertown, New York. Experience its luxurious vibes while enjoying a variety of outdoor activities, all just about 22 miles by car from Chestertown. Staying nearby makes exploring effortless.
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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 waterfront town with a pier, dock, and several buildings.

Top Chestertown Hotel Reviews

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

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

8/10 Good
"Breakfast waffles and other offerings were plentiful even though the theme park was closed. Loved the ice cream across the street at Martha’s Dandee Creme"
Elly 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Surfside On The Lake

Surfside On The Lake

10/10 Excellent
"The property was very well maintained and the room was also well maintained and clean. The reservation stated a view of the lake and it was a partial view which I expected. Overall...Nice. The reason I'm writing this review is to what happened on the 1st night/early morning of our stay. Around 5am the fire alarm woke us up! We could smell burning (plastic?) no smoke yet, but proceeded to evacuate the building. We waited outside for First Responders after my husband and the staff called 911. After they arrived, extinguished the fire, and cleared the building, Kris from the office found us and apologized. She let us know that the room would be "comped" for the night and set us up in a different building with an even better room. The rest of our stay was wonderful. We loved the new room better than the one that we originally booked! Thanks Kris!! When we make reservations to return to the Surfside next year....we will definitely be booking the better room, funny how things work out😊 Thanks again M. Bonestell"
maria 3-night trip
Posted 2 hours ago
Surfside On The Lake
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"This hotel was beautiful. No complaints about anything. Their attention to detail in this hotel is top notch"
Linda 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Lake George
The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"Everything was great....the staff was friendly, and very helpful.......will be back"
Russel 3-night trip
Posted 2 hours ago
The Georgian Lakeside Resort
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Was a good stay."
Deodat 2-night trip
Posted 5 hours ago
Great Escape Lodge & Indoor Waterpark
Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

8/10 Good
"The outside balcony was fantastic. We love sitting there and looking at the lake in the morning and the evening. The bed was hard as a rock and the mattress needs replaced as we both woke up with sore hips every morning. The HVAC unit needs a good cleaning as there is some dust accumulation on the vents. The toilet paper holder also needs to be fixed as it just hangs down. We stayed in the same room (502) just last year and found nothing has changed. We love the convenience of being able to walk everywhere and the food is wonderful everywhere."
chris 3-night trip
Posted 20 hours ago
Courtyard by Marriott Lake George
Nordick's Inn

Nordick's Inn

8/10 Good
"Great location, a short walk to the center of town (under 10 minutes), friendly staff. Parking available."
Gokul 1-night trip
Posted 1 day ago
Nordick's Inn
Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent
"Everything was above my expectations. However found the bed to be a little uncomfortable. On a good note, the restaurant looked amazing. The little bar that we sat in was absolutely adorable and so friendly."
Donna 1-night trip
Posted 1 day ago
Holiday Inn Resort Lake George - Adirondack Area by IHG
Super 8 by Wyndham Lake George/Downtown

Super 8 by Wyndham Lake George/Downtown

8/10 Good
"👍"
Shaheen 2-night trip
Posted 3 days ago
Super 8 by Wyndham Lake George/Downtown

More cheap stays in Chestertown

Days Inn by Wyndham Queensbury/Lake George

Days Inn by Wyndham Queensbury/Lake George

24 Big Boom Rd Queensbury NY
$60 nightly
$67 total
Sep 29 - Sep 30
Total with taxes and fees
Days Inn by Wyndham Queensbury/Lake George
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln Queensbury NY
$74 nightly
$82 total
Sep 27 - Sep 28
Total with taxes and fees
Baymont by Wyndham Queensbury / Lake George
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

435 Canada Street Lake George NY
$93 nightly
$103 total
Sep 27 - Sep 28
Total with taxes and fees
Adirondack Retreat Inn & Suites
The Georgian Lakeside Resort

The Georgian Lakeside Resort

384 Canada Street Lake George NY
$97 nightly
$108 total
Sep 27 - Sep 28
Total with taxes and fees
The Georgian Lakeside Resort
Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets

1454 State Route 9 Lake George NY
$106 nightly
$117 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Spark by Hilton Lake George Outlets
Surfside On The Lake

Surfside On The Lake

400 Canada Street Lake George NY
$121 nightly
$135 total
Oct 12 - Oct 13
Total with taxes and fees
8/10 Very Good! (837 reviews)
Surfside On The Lake

Hotels in Chestertown with star-rating

Find out more about Chestertown

Top reasons to visit Chestertown

  • Outdoor Adventures: Chestertown is a paradise for outdoor enthusiasts, offering skiing, hiking, and water activities amidst stunning natural scenery.
  • Charming Downtown: Stroll through the quaint downtown area, featuring unique shops, local eateries, and picturesque views.
  • Scenic Lakes and Beaches: Enjoy beautiful lakes and relaxing beaches perfect for sunbathing and picnicking.
  • Family-Friendly Activities: The Emmorton Recreation area provides fun and engaging experiences for the whole family.
  • Diverse Accommodations: Choose from cozy lodges to unique agritourism properties for a comfortable stay.

Find great hotels near Chestertown

Chestertown offers a variety of hotel accommodations to cater to every traveler's needs, from cozy lodges to unique agritourism properties. Whether you're seeking adventure, a family-friendly getaway, or a pet-friendly experience, you'll find plenty of options. Explore the best hotels in Chestertown, where comfort and convenience meet the charm of this beautiful area.

  • Super 8 by Wyndham Lake George/Warrensburg Area: A budget-friendly motel with a solid guest rating of 8.8, Super 8 by Wyndham Lake George/Warrensburg Area is located 12 miles from Chestertown. Ideal for travelers seeking a pet-friendly environment, this hotel welcomes furry companions with specific pet policies. The property caters to both leisure and business travelers, offering practical amenities that ensure a comfortable stay. Guests appreciate the clean and cozy rooms, along with the convenience of being close to local attractions.
  • The Alpine Lodge: A charming 3-star lodge boasting a guest rating of 9.0, The Alpine Lodge is situated 10 miles from Chestertown and is perfect for those seeking adventure and romance. With easy access to ski shuttles and lifts, this lodge is a winter wonderland for skiers and snowboarders. It features an array of exciting outdoor activities, such as mountain climbing, kayaking, and horseback riding. For couples, the lodge offers special romance packages, including champagne service, making it an ideal setting for a memorable getaway.
  • North Creek Lodge at Gore Mountain: Rated 3.5 stars and located 10 miles from Chestertown, North Creek Lodge at Gore Mountain is tailored for adventure enthusiasts. This lodge provides various recreational activities nearby, including hiking, snowboarding, and cave exploring. Guests can immerse themselves in nature while enjoying the comfort of well-appointed accommodations. With its focus on outdoor experiences, this lodge is a great choice for travelers looking to explore the stunning landscapes and partake in thrilling adventures.

Where to stay in and around Chestertown

Chestertown, New York, offers a delightful blend of outdoor adventures and scenic beauty, perfect for those seeking a relaxing getaway. Explore the charming downtown area, take in picturesque views of the Chesapeake Bay, or enjoy the Emmorton Recreation area for family-friendly activities. Nearby, you'll find trendy neighborhoods that cater to luxury and adventure, ensuring a memorable vacation filled with various vibes—from secluded retreats to vibrant recreational experiences.

  • Bolton Landing: Located 10 miles from Chestertown, Bolton Landing is a charming destination celebrated for its stunning outdoor scenery and romantic ambiance. With a peak tourist season from June to August, visitors flock here for golfing at its private country clubs and the picturesque views of the nearby lake and island resort. The area is perfect for those looking to unwind and enjoy the natural beauty, making it a favorite summer getaway for families and couples alike.
  • Brant Lake: Just 3 miles away from Chestertown, Brant Lake is a hidden gem that thrives during the summer months, attracting outdoor enthusiasts and nature lovers. Known for its ski resorts and breathtaking mountain views, this destination is particularly popular from June to August. Visitors can indulge in skiing during the winter or relax by the lake and beach in warmer months. Brant Lake offers a serene escape, perfect for those seeking adventure and relaxation in a beautiful setting.
  • Chester Shores: Nestled around Chestertown, Chester Shores is a delightful neighborhood that draws travelers seeking scenic views and outdoor activities. With peak visitation from July to September, this area is renowned for its skiing opportunities and access to urban parks. The nearby lake and mountains create a picturesque backdrop, making it an ideal spot for romantic getaways or family outings. Chester Shores is where you can truly immerse yourself in nature while enjoying a variety of recreational activities.

Things to do in Chestertown

Chestertown, New York, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Visitors can enjoy skiing at local resorts, explore the scenic beauty of the area, and partake in various outdoor recreational activities. With a range of entertainment options, local attractions, and wellness retreats, Chestertown offers a delightful blend of adventure and relaxation for everyone looking to unwind in nature.

Shopping

In Chestertown, enjoy local shops like the Chestertown Farmer's Market for unique gifts and handmade souvenirs. If you're up for a drive, visit the Lake George Plaza, about 12 miles away, featuring various stores and dining options for a more extensive shopping experience.

Recreation

In Chestertown, the Adirondack Wellness Center provides holistic therapies, yoga classes, and serene nature walks, promoting relaxation and rejuvenation. Enjoy the nearby Loon Lake, perfect for kayaking and fishing, offering a peaceful escape into nature while enhancing your well-being.

Adventure

Chestertown offers thrilling adventures at the nearby Adirondack Mountains, where you can hike scenic trails, kayak on serene lakes, and enjoy breathtaking views. Explore the Hudson River for fishing and whitewater rafting, or visit the local parks for biking and nature walks amidst beautiful landscapes.

Nightlife

Chestertown offers a cozy nightlife with local charm. Enjoy a drink at the friendly Loon Lake Lodge or experience live music at the charming Chestertown Community Theatre. For a relaxed evening, grab a bite at a local diner and soak in the small-town atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chestertown

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are March to April and November, where the prices are slightly lower. This is in comparison to July to September, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool makes it easy for you to choose your budget, preferred location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you find the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chestertown with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chestertown

Chestertown, New York, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering stunning scenery and a variety of attractions. Visitors can explore beautiful lakes, relaxing beaches, and charming island resorts. Whether you're looking for adventure or a peaceful retreat, Chestertown's local points of interest provide an ideal setting for memorable experiences amidst nature.

  • Friends Lake: Nestled in Chestertown, Friends Lake offers a serene escape with its beautiful outdoor scenery. Enjoy romantic strolls along the shore, picnics on the beach, and various water activities, making it perfect for relaxation and adventure alike.
  • Loon Lake Beach: This picturesque beach is a local favorite, providing a tranquil environment for sunbathing, swimming, and enjoying the scenic views. It's an ideal spot for families and friends to unwind and soak in the sun.
  • The Sagamore Golf Club: Located 8 miles from Chestertown, this exclusive island resort boasts a stunning golf course with panoramic views. Experience world-class golfing amidst lush landscapes and unwind at the luxurious amenities available on-site.

Best time to go to Chestertown

The best time to visit Chestertown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chestertown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chestertown falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.3°F (-6.5°C)Light RainMostly CloudyAverageAverage
February22.3°F (-5.4°C)Light RainMostly CloudyAverageAverage
March30.4°F (-0.9°C)Light RainMostly CloudyAverageSlightly Low
April42.6°F (5.9°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.1°F (17.3°C)Light RainMostly SunnySlightly HighAverage
July69.1°F (20.6°C)Light RainMostly SunnySlightly HighSlightly High
August67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyAverageSlightly High
October48.6°F (9.2°C)Light RainMostly CloudySlightly LowAverage
November36.1°F (2.3°C)Light RainMostly SunnySlightly LowSlightly Low
December27.5°F (-2.5°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Chestertown

When visiting Chestertown, New York, you have several airport options within a reasonable distance. ALBany International Airport (ALB) is 63 miles away, with nearby hotels like The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. Burlington International Airport (BTV) is 65 miles from Chestertown, offering accommodations such as DoubleTree by Hilton Burlington Vermont, just 2 miles away. Lastly, Plattsburgh International Airport (PBG) is 72 miles distant, with options like Days Inn by Wyndham Plattsburgh, located 2 miles from the airport. Each airport provides accessible transportation services to their respective hotels.

Frequently asked questions

What is the best area to stay in Chestertown?
The best area to stay in Chestertown is near the town center, particularly along Main Street and around Chestertown's central lake, Loon Lake.This area provides convenient access to local shops, eateries, and recreational activities. Main Street is where many of the town's small businesses are located, and Loon Lake offers opportunities for water-based recreation and scenic views. It's a nice setting that balances convenience with natural beauty.Families will find this area particularly suitable due to its proximity to both town amenities and outdoor activities. Loon Lake has public access points for swimming and picnicking, and the nearby parks offer playgrounds and open spaces for children. The ease of walking to local ice cream shops and casual restaurants also makes it a stress-free choice for families.Couples looking for a relaxing getaway will also appreciate the Chestertown center. You can enjoy strolls along the lake, visit local antique shops, or have a quiet dinner at one of the town's restaurants.
What are the best hotels in Chestertown that travelers recommend?
Two highly recommended hotels in Chestertown are The Fern Lodge and Pine Tree Motel & Cabins.The Fern Lodge, a 3.5-star hotel with a great 10.0 rating, offers a luxurious experience with amenities such as a fireplace, premium bedding, and designer toiletries. Guests can enjoy stunning lake, mountain, and river views from their rooms. Friends Lake is conveniently located just 0.3 miles away.Another excellent choice is the Pine Tree Motel & Cabins, which boasts a 9.2 rating. This accommodation provides comfortable rooms with air conditioning and premium bedding. It is well-suited for families, offering a playground, beach toys, and various games and toys for children. Loon Lake Beach is a short 0.5 miles away, and Loon Lake is 1.6 miles from the property.
What are the best family hotels in Chestertown?
For family-friendly hotels in Chestertown, consider the Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing or the Pine Tree Motel & Cabins.The Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing, with a superb 10.0 rating, is an excellent choice for families. It offers a variety of amenities to keep children entertained, including an outdoor play area, a travel crib, games, books, and a playground. The cabin also features a sofa bed for additional sleeping arrangements. It is conveniently located near Friends Lake, just 2.0 miles away, and Loon Lake, 2.5 miles away.Another great option is the Pine Tree Motel & Cabins, which has a 9.2 rating. This property provides a playground, beach toys, books, and games for children, as well as toys for babies and free cribs. Guests have praised its good location and comfortable rooms. It is situated close to Loon Lake, 1.6 miles away, and Loon Lake Beach, 0.5 miles away. Find more child-friendly accommodations in Chestertown
What are the best spa hotels in Chestertown?
For a highly-rated spa hotel in Chestertown, The Fern Lodge is an excellent choice.This 3.5-star hotel boasts a superb 10.0 rating and offers massage services for a relaxing stay. Guests consistently praise the amazing staff. The Fern Lodge also provides mountain views and is located in a mountainous area, offering a serene environment. Additionally, guests can enjoy a free local breakfast. See all spa hotels in Chestertown
What hotels in Chestertown offer free breakfast?
For hotels in Chestertown that offer free breakfast, The Fern Lodge is an excellent option.The 3.5-star Fern Lodge, with a great 10.0 rating, provides a complimentary daily breakfast to all guests. This hotel is praised by customers for its amazing staff and offers stunning views of both mountains and a lake. It is conveniently located just 0.3 miles from Friends Lake and provides mountain bikes on-site for guest use. Find more hotels with free breakfast in Chestertown
What are the best budget hotels in Chestertown?
For a highly-rated budget hotel in Chestertown, consider the Pine Tree Motel & Cabins.This hotel has an excellent 9.2 rating and offers comfortable rooms, as noted by many guests. It provides convenient free parking for RVs, buses, and trucks, as well as complimentary self-parking for all guests. You will also find free WiFi and complimentary toiletries. The motel is well-located for enjoying the natural surroundings, with mountains nearby and mountain biking opportunities. It is also just 0.5 miles from Loon Lake Beach and 1.6 miles from Loon Lake. View all budget hotels in Chestertown
What are the most romantic hotels in Chestertown for couples?
For a romantic getaway in Chestertown, The Fern Lodge is an exceptional choice for couples.The Fern Lodge, a 3.5-star hotel with a superb 10.0 rating, offers a truly intimate experience. Guests frequently praise the amazing staff and the complimentary local breakfast. Many rooms feature a private hot tub, a cozy fireplace, and stunning views of the surrounding mountains and nearby Friends Lake, which is just 0.3 miles away. The lodge also provides convenient access to mountain biking and a sauna, making it ideal for both relaxation and outdoor activities. See all romantic hotels in Chestertown
What are the best hotels in Chestertown near Loon Lake?
For hotels in Chestertown near Loon Lake, consider the Pine Tree Motel & Cabins, Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing, Save on weekly rental & Mon to Thurs. Perfect for Ski Holidays or Summer Fun, and Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.The Pine Tree Motel & Cabins, with a 9.2 rating, is located 1.6 miles from Loon Lake and just half a mile from Loon Lake Beach. It offers a playground for children, a sofa bed, and various toys for children and babies, making it suitable for families. Guests have described the location as good and the rooms as comfortable.Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing, rated 10.0, is 2.5 miles from Loon Lake and 1.1 miles from Loon Lake Beach. This cabin features an outdoor play area, a travel crib, and games and books for children, suiting families.Save on weekly rental & Mon to Thurs. Perfect for Ski Holidays or Summer Fun, with a 9.4 rating, is very close to Loon Lake, at 1.4 miles, and only 0.1 miles from Loon Lake Beach. This option provides a playground and an outdoor play area for children, along with a stair gate for added safety.Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer, with a 9.2 rating, is also conveniently located 1.4 miles from Loon Lake and 0.1 miles from Loon Lake Beach. It features a kitchen, an outdoor play area, and a playground for children.
When is the best time to go to Chestertown?
The best time to visit Chestertown, New York, is during the summer months, from June to August, and again in the fall, from September to October.Summer offers ideal weather for enjoying the area's many outdoor activities. The average daily temperature hovers around 75°F (24°C), making it superb for swimming, boating, and hiking in the nearby Adirondack Mountains. This is also when many local events and festivals take place, providing a lively option. Couples and families will find plenty to do, from exploring Loon Lake to enjoying lakeside dining.For those who appreciate scenic beauty and cooler temperatures, the fall is an exceptional time to visit. The Adirondacks transform with vibrant autumn foliage, typically peaking in late September to early October. The weather is crisp and pleasant, with average temperatures around 60°F (15°C), which is well-suited for hiking, scenic drives, and enjoying the quiet charm of the town.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chestertown.
How much is the nightly rate at a Chestertown hotel?
Prices for hotels in Chestertown often vary, but you can find a great deal from $67 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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