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

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Check prices for these dates

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

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 ￥23,747
￥70,290 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥13,773
￥31,630 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥15,673
￥39,087 total
includes taxes & fees
Oct 13 - Oct 14
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
A compact living space with a wooden ceiling, a sofa, a dining table, and a TV mounted on the wall.

4. 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 ￥16,623
￥40,311 total
includes taxes & fees
Oct 13 - Oct 14
The Office at North Creek All Season Rental
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 ￥15,673
￥39,087 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
A cozy living room with a sofa, a television, a fireplace, and a bookshelf.

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 ￥29,604
￥53,244 total
includes taxes & fees
Oct 13 - Oct 14
Lovely 3-bedroom house close to Gore Mountain for skiing.
A porch with green railings and red rocking chairs.

7. 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 ￥17,810
￥58,781 total
includes taxes & fees
Oct 13 - Oct 14
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
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 ￥21,372
￥42,934 total
includes taxes & fees
Oct 25 - Oct 26
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.

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is ￥124,273
￥307,737 total
includes taxes & fees
Oct 14 - Oct 15
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.

10. 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 ￥59,208
￥1,024,107 total
includes taxes & fees
Nov 1 - Nov 2
Gore Mountain Views | Luxury Lodge for 12 | Pets
A small, single-bed room with wooden walls, a window, and a door.

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, (1 review)
"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 ￥27,783
￥63,700 total
includes taxes & fees
Oct 13 - Oct 14
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. 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, (32 reviews)
"Our 3rd time staying here and it's always wonderful!"
United States
Blair G.
The price is ￥63,324
￥99,460 total
includes taxes & fees
Oct 13 - Oct 14
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
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 ￥28,496
￥40,768 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥22,955
￥67,630 total
includes taxes & fees
Oct 14 - Oct 15
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A wooden deck with outdoor furniture, a grill, and a view of a forested area.

15. 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)
"Great house for a large group, ample space and great amenities, clean, great support by lakegeorgevacay."
United States
Chris B.
The price is ￥365,734
￥601,880 total
includes taxes & fees
Oct 18 - Oct 19
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.

16. 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 ￥37,203
￥86,996 total
includes taxes & fees
Oct 13 - Oct 14
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.

17. 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 ￥47,730
￥115,012 total
includes taxes & fees
Oct 14 - Oct 15
Copeland Cabin - Charming Lake House in the Adirondacks
A cabin with a view of a stream and surrounding trees.

18. 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 ￥39,578
￥56,232 total
includes taxes & fees
Oct 13 - Oct 14
Three Bedroom House Lake George
A dining area with a large table, chairs, and a view of autumn trees through large windows.

19. Luxurious Lake George Getaway

Luxurious Lake George Getaway
Lake George
9.8 out of 10, Exceptional, (16 reviews)
"Great house for a relaxing vacation for our family. Very clean. Everything was well stocked. Location was perfect to be able to do things in Lake George downtown and Bolton Landing. Very quiet. Was able to see the fireworks from the shared dock."
United States
IRIS L.
The price is ￥72,348
￥150,947 total
includes taxes & fees
Oct 27 - Oct 28
Luxurious Lake George Getaway
A swimming pool with a glass ceiling structure, surrounded by chairs and a view of greenery outside.

20. Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE

Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE
Lake George
10.0 out of 10, Exceptional, (2 reviews)
"Great location to all that Lake George has to offer. Staff and management were very helpful and nice. Parking gets a little tight in the evenings sometimes but it’s a poplar place during the summer months."
United States
Michelle T.
The price is ￥76,780
￥100,585 total
includes taxes & fees
Oct 14 - Oct 15
Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL 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

Lodge at Schroon Lake

Lodge at Schroon Lake

10/10 Excellent
"Great place to visit"
Marco 2-night trip
Posted 1 hour ago
Lodge at Schroon Lake

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
270
Accommodation
538 Vacation Homes
Lowest Price
￥31,630
Highest Price
￥1,024,107