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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chestertown holiday homes

Pair your adventure with the comfort of our cozy vacation rental, and create memories filled with the flavors of the Adirondacks. Cheers to local taste and timeless relaxation!

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 HK$1,177
HK$3,483 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$573
HK$1,428 total
includes taxes & fees
1 Nov - 2 Nov
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)
"Thank you for an amazing stay. Everything was fantastic! "
United States
Tara F.
The price is HK$808
HK$1,963 total
includes taxes & fees
1 Nov - 2 Nov
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
A single-story building with a red door and a garage door.

4. 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 HK$808
HK$1,963 total
includes taxes & fees
31 Oct - 1 Nov
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.

5. 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 HK$857
HK$2,034 total
includes taxes & fees
12 Nov - 13 Nov
The Office at North Creek All Season Rental
A wooden cabin with a porch, wooden furniture, and a view of a forest.

6. 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 HK$1,467
HK$2,639 total
includes taxes & fees
31 Oct - 1 Nov
Lovely 3-bedroom house close to Gore Mountain for skiing.
A log cabin interior with a fireplace, leather seating, and a ceiling fan.

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is HK$6,158
HK$15,250 total
includes taxes & fees
9 Nov - 10 Nov
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A spacious room with a high ceiling and large windows offering a mountain view.

8. 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 HK$2,856
HK$7,434 total
includes taxes & fees
1 Nov - 2 Nov
Gore Mountain Views | Luxury Lodge for 12 | Pets
A sign for 'Ski Bowl Park' with illuminated tree decorations.

9. 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 HK$388
HK$2,364 total
includes taxes & fees
3 Nov - 4 Nov
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
A spacious yurt interior with a wooden dining area, a kitchen with cabinets, and a birch tree.

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 HK$1,059
HK$2,128 total
includes taxes & fees
11 Nov - 12 Nov
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
A wooden room with two large circular windows, a blue floor, and a wooden bench.

11. 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, (54 reviews)
"Overall great time"
United States
Dave C.
The price is HK$1,412
HK$2,081 total
includes taxes & fees
1 Nov - 2 Nov
Sweet New Cabin With Amazing Views Of The Hudson River
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 HK$3,138
HK$4,972 total
includes taxes & fees
11 Nov - 12 Nov
Adirondack Victorian Vacations and Wedding Venue
A single-story building with a red door and a garage door.

13. 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 HK$1,061
HK$3,258 total
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.

14. 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.
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
A spacious living area with a wooden ceiling, a sofa set, a coffee table, and a fireplace.

15. 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 HK$1,451
HK$3,823 total
includes taxes & fees
1 Nov - 2 Nov
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.

16. Copeland Cabin - Charming Lake House in the Adirondacks

Copeland Cabin - Charming Lake House in the Adirondacks
Fort Ann
10.0 out of 10, Exceptional, (49 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is HK$2,323
HK$5,609 total
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.

17. 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 HK$3,389
HK$7,533 total
includes taxes & fees
16 Nov - 17 Nov
Luxurious Lake George Getaway
A modern living room with a flat-screen TV, a black entertainment unit, and a 'Welcome to our home' sign.

18. Cozy 3 bedroom house

Cozy 3 bedroom house
South Glens Falls
8.4 out of 10, Very good, (25 reviews)
"Nice place and location for visit to Saratoga"
United States
Gilison D.
The price is HK$1,294
HK$2,779 total
includes taxes & fees
20 Nov - 21 Nov
Cozy 3 bedroom house
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
"Everything was great we had a great time"
Besnik 3-night trip
Posted 2 days ago
Depe Dene Lakeside Resort

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
365
Accommodation
549 Vacation Homes
Lowest Price
HK$1,428
Highest Price
HK$15,250

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