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

Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (43 reviews)
"Perfect for what we needed as a family of 8,, the host was very easy to communicate with as well."
United States
Sara Beth E.
The price is AU$628
includes taxes & fees
20 Oct - 21 Oct
The Lily Pad at Loon Lake near Gore Mountain
A single-story building with a red door and a garage door.

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

Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
North Creek
9.4 out of 10, Exceptional, (15 reviews)
"The host was very responsive and helpful. The space was very cozy and had all the basics. Location was perfect for a ski weekend."
United States
annie k.
The price is AU$355
includes taxes & fees
18 Oct - 19 Oct
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

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

Gore MTN & Saratoga ADK Crash Pad! The Cocoon
Warrensburg
9.0 out of 10, Wonderful, (2 reviews)
"Good place to stay for a quick trip to lake George"
United States
Matthew L.
The price is AU$310
includes taxes & fees
31 Oct - 1 Nov
Gore MTN & Saratoga ADK Crash Pad! The Cocoon
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.

Lovely 3-bedroom house close to Gore Mountain for skiing.
North Creek
9.4 out of 10, Exceptional, (3 reviews)
"Very cute and cozy / responsive and helpful host"
United States
Renee B.
The price is AU$471
includes taxes & fees
19 Oct - 20 Oct
Lovely 3-bedroom house close to Gore Mountain for skiing.
A single-story building with a red door and a garage door.

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

Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
North Creek
9.0 out of 10, Wonderful, (25 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
The price is AU$355
includes taxes & fees
18 Oct - 19 Oct
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
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

The Office at North Creek All Season Rental
North Creek
8.8 out of 10, Excellent, (13 reviews)
"Fun property to stay at! We enjoyed our stay and hope to come back during ski season. "
United States
Brandon A.
The price is AU$364
includes taxes & fees
27 Oct - 28 Oct
The Office at North Creek All Season Rental
A white building with a red umbrella, a stone chimney, and a black fence in front.

7. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (88 reviews)
"Quiet surroundings and quiet neighbors makes for a restful vacation spot, close to many nature trails and lakes and rivers."
United States
Diana D.
The price is AU$366
includes taxes & fees
18 Oct - 19 Oct
Adirondack Bungalow Getaway
A yurt with an open door, surrounded by rocks and trees, under a sunset sky.

8. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Minerva
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely fantastic! Hosts were very kind and responsive. Property was clean and cozy. "
United States
Christine T.
The price is AU$381
includes taxes & fees
18 Oct - 19 Oct
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
An outdoor seating area with wicker chairs and a wooden bench, overlooking a forested landscape with hills.

9. Gore Mountain Views | Luxury Lodge for 12 | Pets

Gore Mountain Views | Luxury Lodge for 12 | Pets
North Creek
10.0 out of 10, Exceptional, (35 reviews)
"We enjoyed our stay here! "
United States
Jeremy H.
The price is AU$1,320
includes taxes & fees
1 Nov - 2 Nov
Gore Mountain Views | Luxury Lodge for 12 | Pets
A log cabin interior with a fireplace, leather seating, and a ceiling fan.

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is AU$2,673
includes taxes & fees
28 Oct - 29 Oct
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A bedroom with a bed, a nightstand, a window, and wooden walls.

11. Family retreat. 3-br house in serene Bolton Landing. 2 miles to Bolton village.

Family retreat. 3-br house in serene Bolton Landing. 2 miles to Bolton village.
Bolton Landing
10.0 out of 10, Exceptional, (2 reviews)
"Great hosts and great stay. The place was super clean and the hosts were excellent with communication and accommodating our requests. The beds were also very comfortable and the house has an excellent location."
United States
Debra T.
The price is AU$562
includes taxes & fees
24 Oct - 25 Oct
Family retreat. 3-br house in serene Bolton Landing. 2 miles to Bolton village.
A hot tub in a room with wooden walls, two potted plants, and a clock on the wall.

12. Adirondack Victorian Vacations and Wedding Venue

Adirondack Victorian Vacations and Wedding Venue
North Creek
10.0 out of 10, Exceptional, (32 reviews)
"Our 3rd time staying here and it's always wonderful!"
United States
Blair G.
The price is AU$873
includes taxes & fees
18 Oct - 19 Oct
Adirondack Victorian Vacations and Wedding Venue
A porch with green railings and red rocking chairs.

13. 7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
Johnsburg
10.0 out of 10, Exceptional, (5 reviews)
"Nice place and area, nice and quiet"
United States
thomas c.
The price is AU$687
includes taxes & fees
18 Oct - 19 Oct
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
A wooden room with two large circular windows, a blue floor, and a wooden bench.

14. Sweet New Cabin With Amazing Views Of The Hudson River

Sweet New Cabin With Amazing Views Of The Hudson River
North River
9.8 out of 10, Exceptional, (52 reviews)
"Overall great time"
United States
Dave C.
The price is AU$376
includes taxes & fees
7 Nov - 8 Nov
Sweet New Cabin With Amazing Views Of The Hudson River
A single-story building with a red door and a garage door.

15. 6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
North Creek
10.0 out of 10, Exceptional, (3 reviews)
"This is a wonderful location. We thoroughly enjoyed the town of North Creek!"
United States
Jane H W.
The price is AU$592
includes taxes & fees
19 Oct - 20 Oct
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A two-story wooden house with a covered porch and a staircase leading to the upper level.

16. Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
Warrensburg
9.8 out of 10, Exceptional, (63 reviews)
"House was great, experience was even better. Laney was a tremendous host."
United States
Brandon M.
The price is AU$841
includes taxes & fees
18 Oct - 19 Oct
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
An outdoor seating area with four chairs and a square table with a fire pit.

17. Cozy Upstate Adirondack Cottage Getaway

Cozy Upstate Adirondack Cottage Getaway
Warrensburg
9.8 out of 10, Exceptional, (37 reviews)
"Property was very clean. Plenty of room for family of eight. My only complaint is the beds were extremely soft for me. Would consider staying again."
United States
Robin M.
The price is AU$754
includes taxes & fees
19 Oct - 20 Oct
Cozy Upstate Adirondack Cottage Getaway
A spacious living area with a wooden ceiling, a sofa set, a coffee table, and a fireplace.

18. Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces

Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
Lake Luzerene
9.8 out of 10, Exceptional, (17 reviews)
"Great stay. Barn is fun for hanging out with a group. Would recommend bringing your own camp chairs. Hottub was great. House was awesome for cooking and hanging out"
United States
Ryen H.
The price is AU$752
includes taxes & fees
18 Oct - 19 Oct
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
A fire pit with Adirondack chairs in a forested area with a lake view.

19. Copeland Cabin - Charming Lake House in the Adirondacks

Copeland Cabin - Charming Lake House in the Adirondacks
Fort Ann
10.0 out of 10, Exceptional, (48 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is AU$1,052
includes taxes & fees
8 Nov - 9 Nov
Copeland Cabin - Charming Lake House in the Adirondacks
A cabin with a view of a stream and surrounding trees.

20. Three Bedroom House Lake George

Three Bedroom House Lake George
Lake George
6.0 out of 10, (3 reviews)
"House was nice and clean. We did not use any of the amenities "
United States
Madonna G.
The price is AU$496
includes taxes & fees
19 Oct - 20 Oct
Three Bedroom House Lake George
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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Top Chestertown Hotel Reviews

Depe Dene Lakeside Resort

Depe Dene Lakeside Resort

10/10 Excellent
"The lake views were amazing!! The room was big and clean, nice amenities. However the grounds are hard to Navigate. It is a very steep hill bumpy road not well maintained roads"
Carole 3-night trip
Posted 4 hours ago
Depe Dene Lakeside Resort

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
423
Accommodation
559 Holiday Homes
Lowest Price
AU$310
Highest Price
AU$2,673