Chestertown Vacation Homes

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

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Our top choices for Chestertown holiday homes

Private lakefront access just down the road with two docks, a cozy firepit, and comfortable outdoor seating. Perfect for fishing, enjoying the view, or unwinding by the water.

1. The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sara Beth E.

HK$3,354 total

includes taxes & fees

22 Oct - 23 Oct

A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

2. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

Warrensburg

Matthew L.

HK$1,463 total

includes taxes & fees

26 Oct - 27 Oct

A single-story building with a red door and a garage door.

3. Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

North Creek

annie k.

HK$1,920 total

includes taxes & fees

2 Nov - 3 Nov

A cozy living room with a sofa, a television, a fireplace, and a bookshelf.

4. Lovely 3-bedroom house close to Gore Mountain for skiing.

North Creek

Renee B.

HK$2,631 total

includes taxes & fees

25 Oct - 26 Oct

5. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

North Creek

joseph

HK$1,920 total

includes taxes & fees

2 Nov - 3 Nov

A compact living space with a wooden ceiling, a sofa, a dining table, and a TV mounted on the wall.

6. The Office at North Creek All Season Rental

North Creek

Brandon A.

HK$1,998 total

includes taxes & fees

26 Oct - 27 Oct

A white building with a red umbrella, a stone chimney, and a black fence in front.

7. Adirondack Bungalow Getaway

Warrensburg

Diana D.

HK$2,030 total

includes taxes & fees

26 Oct - 27 Oct

A log cabin interior with a fireplace, leather seating, and a ceiling fan.

8. Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

Brant Lake

HK$15,255 total

includes taxes & fees

22 Oct - 23 Oct

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Top Chestertown Hotel Reviews

The Queensbury Hotel

10/10 Excellent

"Very clean and aesthetic rooms. Staff is awesome and pool is the cleanest."

Fort William Henry Hotel and Conference Center

8/10 Good

"The room we had “Grand King Lake view “ was spacious, had a comfortable sectional couch along with a comfy king size bed and incredible view of the lake. The reception desk employees were very friendly and helpful, and so were the girls who clean the room. Breakfast was delicious in the Lakeside restaurant within the hotel. Unfortunately the dining room was not serving dinner the nights we were there, so we didn’t get to try it . There were other great restaurants close by to eat in. The only thing we would have liked to have was coffee 24/7 in the lobby. Most other hotels do offer it. There was a coffee maker in the room, but it never tastes the same as fresh brewed coffee. All in all, we had a wonderful stay and enjoyed going to the museum on the premises ."

The Georgian Lakeside Resort

8/10 Good

"We booked this hotel at the last minute and we were pleasantly surprised. Our room had recently been renovated. It was clean, comfortable, and we were thrilled, but there was flooring instead of a rug. My only complaint was that the rooms were not well insulated so you could hear lots of noise outside when other people were not being considerate of others late at night."

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