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Find hotels in Chestertown, NY from ¥8,124

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Compare 1,491 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Outdoor dining
Cozy Adirondack Cabin w/ Deck [~15 minutes to Gore Mountain]
10.0 out of 10, Exceptional, (4)
"The cabin was perfect for our needs. It was nice and remote enough with plenty to see within a half hour drive. We loved Gore Mt.!"
Cozy Adirondack Cabin w/ Deck [~15 minutes to Gore Mountain]
Smart TV, fireplace, DVD player, books
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
10.0 out of 10, Exceptional, (87)
"The host made us feel welcome. We enjoyed the privacy and the private pond access where canoes & gear were available! Highly recommended!"
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
Beach
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, (36)
"Stay was good"
Adirondack Creekside Cottage-Sportmen’s Delight
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View from property
Lake view , Cozy One Bedroom! Walk to Beach and Town!
10.0 out of 10, Exceptional, (37)
"Apartment was clean and updated. Very responsive host! Enjoyed our stay thank you for being pet friendly!"
Lake view , Cozy One Bedroom! Walk to Beach and Town!
Fridge, microwave, oven, stovetop
Home in Schroon Lake: Walk to lake and town!
10.0 out of 10, Exceptional, (3)
"My husband and I stayed at the house with another couple for a weekend. We needed a place to come to after youth events at nearby Word of Life. It was perfect for our needs. Very clean and communication was great. Very nice host."
Home in Schroon Lake: Walk to lake and town!
Aerial view
Tripp Pond Retreat, Unit E | Condo in Warrensburg
10.0 out of 10, Exceptional, (1)
"Perfect for us - we traveled with 2 grandchildren, 8 and 12. The condo was very clean, has a well equipped kitchen, and the tennis courts, pickle ball courts and basketball court were right outside the door. The grill in the outdoor porch worked well. Beach, with chairs, umbrellas and boats was a 3 minute walk down from the condo. Would definitely return!"
Tripp Pond Retreat, Unit E | Condo in Warrensburg
Restaurant
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (42)
"Paradise just simply heavenly. And so well appointed. Feel so at home"
The price is ¥93,574
per night
May 26 - May 27
The Fern Lodge
Dining
Welcome home!
9.8 out of 10, Exceptional, (49)
"This house is so cozy and comfortable. The host was very easy to work with and the hospitality was 110%. This area is great for short pretty hikes and near Lake George. We enjoyed our short stay and would you love to return in the summer or fall."
Welcome home!
2 bedrooms, iron/ironing board, travel crib, WiFi
Lily Pad South at Loon Lake near Gore Mountain
9.8 out of 10, Exceptional, (39)
"What I loved most was it was like staying in your own home, quiet, clean, and private. The only drawback was no coffee in the kitchen. Otherwise absolutely give stars. I want to stay in this exact house again if welcome. They were very nice, too, and accommodating. "
Lily Pad South at Loon Lake near Gore Mountain
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
9.6 out of 10, Exceptional, (14)
"John and Yvonne were the perfect hosts hosts...Tvicolorfulsunse"
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Front of property
Silver Bay Inn and Conference Center
3.0 star property
9.6 out of 10, Exceptional, (38)
"Excellent "
The price is ¥13,140
per night
May 16 - May 17
Silver Bay Inn and Conference Center
Fridge, microwave, oven, dishwasher
Adirondack style condo on Tripp lake and near Gore Mt. Ski resort
9.6 out of 10, Exceptional, (17)
"My partner and I stayed here to see the solar eclipse. The place was nice getaway for a mini vacation. We had everything we needed for cookware to make meals. Not too far was a place where we could cross country ski in some wooden area and not a bad drive to Mount Von Hoevenberg."
Adirondack style condo on Tripp lake and near Gore Mt. Ski resort
Front of property - evening/night
Boathouse Waterfront Lodging
3.5 star property
9.4 out of 10, Exceptional, (17)
"Fantastic views and premium lake access. Close enough to walk to great coffee, food, shops. We loved it and will com back!"
Boathouse Waterfront Lodging
Exterior
Ultimate couples getaway! Quiet and private Lakeside Cottage in the Adirondacks
9.4 out of 10, Exceptional, (39)
"Super"
Ultimate couples getaway! Quiet and private Lakeside Cottage in the Adirondacks
Luxury Studio Suite, 1 King Bed, Lake View (#1) | Lake view
Chateau Rooms
4.5 star property
9.2 out of 10, Wonderful, (38)
"The owner upgraded our room so we were facing Lake George. Our room was beautiful with a balcony. We sat in the room and watched three deer by the lake. The manager was very prompt and helpful with a small issue we had. "
Chateau Rooms
Property grounds
SKI TIME! Adirondack Waterfront Log Cabin
9.2 out of 10, Wonderful, (68)
"This was a 5-day, large family, vacation. There were a few minor issues, but nothing we couldn't overcome. We absolutely loved the location. There were a couple of days that we didn't even leave the property. The mosquitos were horribly, horribly bad! We went through a lot of insect spray and tiki torch fuel, but we were prepared for them. Thanks, Lisa"
SKI TIME! Adirondack Waterfront Log Cabin
Exterior
Pine Tree Motel & Cabins
2.0 star property
9.0 out of 10, Wonderful, (113)
"Cutest cabins, friendly owners, dog friendly ❤️ supporting small businesses definitely going back next year. "
The price is ¥27,340
per night
May 16 - May 17
Pine Tree Motel & Cabins
Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn
4.0 star property
9.0 out of 10, Wonderful, (77)
"The food was made to order and very good prices were fair. The cost to stay there is overpriced."
The price is ¥44,060
per night
May 16 - May 17
Friends Lake Inn
Aerial view
Condo with private community beach/pond access - on-site tennis & golf nearby
9.0 out of 10, Wonderful, (6)
"The stay was great! The property had all basic necessities to last our time there. There was a bit of confusion about trash disposal but the neighbors were kind. Our WiFi service was a bit spotty but otherwise no other complaints. Would recoommend!"
The price is ¥8,124
per night
May 16 - May 17
Condo with private community beach/pond access - on-site tennis & golf nearby
Exterior
Lodge at Schroon Lake
2.0 star property
8.8 out of 10, Excellent, (139)
"Walking distance to dining options that have more budget friendly price"
The price is ¥18,459
per night
May 19 - May 20
Lodge at Schroon Lake
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Chestertown hotels information

Number of reviews
6,218
Accommodation
1,491 hotels
Lowest Price
¥8,124
Highest Price
¥93,574

Frequently asked questions

Where is the best place to stay in Chestertown?

Located 21.4 mi (34.5 km) from the heart of Chestertown, Six Flags Lodge & Indoor Waterpark is a top choice for your stay based on our traveler data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham Lake George and The Queensbury Hotel. See all available top hotels, or vacation rentals in Chestertown.

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

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace: This vacation home rental outside Chestertown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books. 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 that most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about changing or cancelling your trip to Chestertown, head over to our customer service page.

What's the best accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Pine Tree Motel & Cabins is a popular 2-star property for our travelers looking for an economical choice, and features free WiFi and free parking. View all budget hotels in Chestertown.

What's the best accommodation for a family vacation in Chestertown?

Pine Tree Motel & Cabins is a property with free parking and free WiFi, and it's a top choice on Expedia for families. The Fern Lodge is another choice for your family trip. Attractions in the area like Garnet Hill Lodge and Ski Resort and House of Frankenstein Wax Museum are also fun for kids of all ages. Find more child-friendly accommodations in Chestertown.

What's the best hotel for couples in Chestertown?

Friends Lake Inn is a favorite 4-star hotel for couples, and features a full-service spa and wedding services. Another choice for a romantic stay is The Fern Lodge. See all romantic hotels in Chestertown.

What's the best LGBTQ-friendly place to stay 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 pet-friendly accommodation in Chestertown?

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is a top lodge for people traveling with their pets, and offers an arcade/game room and in-room kitchens for its human guests. Pine Tree Motel & Cabins is another good choice if you're bringing your pet along. See more pet-friendly hotel accommodations in Chestertown.

What's the best place to stay close to Loon Lake Beach?

Pine Tree Motel & Cabins is one of the top choices for your stay based on our traveler data, and this property offers free WiFi and free parking. It's located just a short 0.5 mi (0.8 km) from Loon Lake Beach. Another good choice is Friends Lake Inn, located 1.6 mi (2.6 km) away.

What's the best hotel for a beach vacation in Chestertown?

The Fern Lodge is a top beach B&B with free breakfast and 8 spa tubs, and it's located close to Loon Lake Beach. See more stays near the beach in Chestertown.

What's the best luxury place to stay in Chestertown?

Friends Lake Inn is a 4-star hotel with a full-service spa and a terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Chestertown.

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