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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 €377
includes taxes & fees
25 Oct - 26 Oct
The Lily Pad at Loon Lake near Gore Mountain
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

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 €169
includes taxes & fees
25 Oct - 26 Oct
Gore MTN & Saratoga ADK Crash Pad! The Cocoon
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

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 €226
includes taxes & fees
23 Oct - 24 Oct
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
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 €300
includes taxes & fees
25 Oct - 26 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, (26 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
The price is €221
includes taxes & fees
25 Oct - 26 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 €228
includes taxes & fees
25 Oct - 26 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, (89 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 €234
includes taxes & fees
25 Oct - 26 Oct
Adirondack Bungalow Getaway
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 Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is €1,702
includes taxes & fees
26 Oct - 27 Oct
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
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 €926
includes taxes & fees
9 Nov - 10 Nov
Gore Mountain Views | Luxury Lodge for 12 | Pets
A yurt with an open door, surrounded by rocks and trees, under a sunset sky.

10. 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 €242
includes taxes & fees
25 Oct - 26 Oct
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
A porch with green railings and red rocking chairs.

11. 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 €340
includes taxes & fees
27 Oct - 28 Oct
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
A dining area with a wooden table and chairs, large windows, and a view of trees.

12. 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 €355
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.

13. 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 €556
includes taxes & fees
23 Oct - 24 Oct
Adirondack Victorian Vacations and Wedding Venue
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, (53 reviews)
"Overall great time"
United States
Dave C.
The price is €236
includes taxes & fees
1 Nov - 2 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 €367
includes taxes & fees
1 Nov - 2 Nov
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 €520
includes taxes & fees
26 Oct - 27 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, (38 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 €471
includes taxes & fees
25 Oct - 26 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 €430
includes taxes & fees
25 Oct - 26 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 €675
includes taxes & fees
8 Nov - 9 Nov
Copeland Cabin - Charming Lake House in the Adirondacks
A dining area with a large table, chairs, and a view of autumn trees through large windows.

20. Luxurious Lake George Getaway

Luxurious Lake George Getaway
Lake George
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful home and in a great location!"
United States
Jennifer H.
The price is €863
includes taxes & fees
8 Nov - 9 Nov
Luxurious Lake George Getaway
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

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

8/10 Good
"Dejeuner excellent, propreté pourrait être relevé un peu partout."
Pierre 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Lake George

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
439
Accommodation
538 Holiday Homes
Lowest Price
€169
Highest Price
€1,702