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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chestertown vacation 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 AED 551
AED 1,631 total
includes taxes & fees
5 Oct - 6 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
10.0 out of 10, Exceptional, (1 review)
"Good place to stay for a quick trip to lake George"
United States
Matthew L.
The price is AED 314
AED 724 total
includes taxes & fees
4 Oct - 5 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 AED 364
AED 903 total
includes taxes & fees
26 Oct - 27 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 AED 693
AED 1,242 total
includes taxes & fees
6 Oct - 7 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, (24 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
The price is AED 375
AED 919 total
includes taxes & fees
26 Oct - 27 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 AED 444
AED 1,013 total
includes taxes & fees
2 Nov - 3 Nov
The Office at North Creek All Season Rental
A yurt with an open door, surrounded by rocks and trees, under a sunset sky.

7. 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 AED 496
AED 996 total
includes taxes & fees
4 Oct - 5 Oct
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
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 AED 2,883
AED 7,124 total
includes taxes & fees
5 Oct - 6 Oct
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A porch with green railings and red rocking chairs.

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 AED 413
AED 1,364 total
includes taxes & fees
5 Oct - 6 Oct
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
A small, single-bed room with wooden walls, a window, and a door.

10. 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
The price is AED 645
AED 1,478 total
includes taxes & fees
4 Oct - 5 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.

11. GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
North Creek
10.0 out of 10, Exceptional, (31 reviews)
"Our 3rd time staying here and it's always wonderful!"
United States
Blair G.
The price is AED 1,469
AED 2,308 total
includes taxes & fees
4 Oct - 5 Oct
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
A log cabin with a deck, outdoor seating, and a fire pit.

12. 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 AED 1,723
AED 3,869 total
includes taxes & fees
1 Nov - 2 Nov
Gore Mountain Views | Luxury Lodge for 12 | Pets
A wooden room with two large circular windows, a blue floor, and a wooden bench.

13. 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 AED 661
AED 950 total
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.

14. 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 AED 610
AED 1,667 total
includes taxes & fees
14 Oct - 15 Oct
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A room with a wooden bed, two bedside lamps, a ceiling fan, a framed picture on the wall, and a window with a view of trees.

15. Hot Tub • Sauna • 5 Min to Gore Mountain

Hot Tub • Sauna • 5 Min to Gore Mountain
North Creek
9.2 out of 10, Wonderful, (23 reviews)
"Perfect house for our family ski weekend at Gore! We loved the hot tub and plenty of beds and baths for everyone. Great communication with the manager and easy rental experience. Would definitely rent again."
United States
Lisa B.
Hot Tub • Sauna • 5 Min to Gore Mountain
A wooden deck with outdoor furniture, a grill, and a view of a forested area.

16. Sagamore Golf House|Wine Cellar|Movie Theater|15 beds|Hot Tub|Pet Friendly|

Sagamore Golf House|Wine Cellar|Movie Theater|15 beds|Hot Tub|Pet Friendly|
Bolton Landing
10.0 out of 10, Exceptional, (20 reviews)
"The house is massive, was very clean, and had so much to do. Great location and the hosts were very hospitable, nice, and helpful. We will definitely stay again."
United States
George C.
Sagamore Golf House|Wine Cellar|Movie Theater|15 beds|Hot Tub|Pet Friendly|
A spacious living area with a wooden ceiling, a sofa set, a coffee table, and a fireplace.

17. 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 AED 826
AED 1,974 total
includes taxes & fees
25 Oct - 26 Oct
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
A lakeside dock with boats, chairs, and a clear view of the lake and mountains.

18. Bolton Beach House|8 beds|Hot Tub|Lake Access|Pet Friendly|

Bolton Beach House|8 beds|Hot Tub|Lake Access|Pet Friendly|
Bolton Landing
10.0 out of 10, Exceptional, (17 reviews)
"The Bolton Beach House is a perfect location across from the beach, playground, public docks, and close walking distance to town. Plenty of space for all and something for everyone, including a great game room, coffee bar and beautiful outdoor setting. This is maybe our 5th time staying here & is definitely a favorite!"
United States
Diane D.
The price is AED 5,412
AED 9,214 total
includes taxes & fees
9 Oct - 10 Oct
Bolton Beach House|8 beds|Hot Tub|Lake Access|Pet Friendly|
A cabin with a view of a stream and surrounding trees.

19. 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 AED 918
AED 1,305 total
includes taxes & fees
4 Oct - 5 Oct
Three Bedroom House Lake George
A fire pit with Adirondack chairs in a forested area with a lake view.

20. Copeland Cabin - Charming Lake House in the Adirondacks

Copeland Cabin - Charming Lake House in the Adirondacks
Fort Ann
10.0 out of 10, Exceptional, (47 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is AED 1,329
AED 2,926 total
includes taxes & fees
5 Oct - 6 Oct
Copeland Cabin - Charming Lake House in the Adirondacks
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

Lodge at Schroon Lake

Lodge at Schroon Lake

10/10 Excellent
"What a beautiful spot! The property is well maintained and the staff are helpful and friendly. The grounds offer so many options for fun activities, and there are no additional fees to guests to use them! The evening fire pits and smores were a nice touch. We definitely plan to return!"
Laurie 1-night trip
Posted 10 hours ago
Lodge at Schroon Lake