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

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chestertown holiday homes

A view through a window of a deck area with outdoor furniture and a barbecue grill.

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$1,396
HK$3,760 total
includes taxes & fees
9 Sept - 10 Sept
The Lily Pad at Loon Lake near Gore Mountain
A bedroom with a bed, a window with blinds, a wall-mounted air conditioner, and a framed picture above the bed.

2. Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (122 reviews)
"Great house. Great location"
United States
David S.
The price is HK$2,156
HK$5,674 total
includes taxes & fees
13 Sept - 14 Sept
Eagles Nest at Loon Lake near Gore Mountain
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
The price is HK$677
HK$1,561 total
includes taxes & fees
8 Sept - 9 Sept
Gore MTN & Saratoga ADK Crash Pad! The Cocoon
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 HK$847
HK$2,031 total
includes taxes & fees
14 Sept - 15 Sept
The Office at North Creek All Season Rental
A white building with a red umbrella, a stone chimney, and a black fence in front.

5. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (84 reviews)
"Enjoyed our weekend stay here. Close to the main road and a short drive to Lake George. House was very clean and met all our needs. Will definitely stay here again if we visit the area."
United States
Virginia (Ginger) S.
The price is HK$769
HK$1,515 total
includes taxes & fees
13 Sept - 14 Sept
Adirondack Bungalow Getaway
A single-story building with a red door and a garage door.

6. 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 HK$902
HK$2,101 total
includes taxes & fees
7 Sept - 8 Sept
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.

7. 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$1,466
HK$2,637 total
includes taxes & fees
7 Sept - 8 Sept
Lovely 3-bedroom house close to Gore Mountain for skiing.
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, (1 review)
"Absolutely fantastic! Hosts were very kind and responsive. Property was clean and cozy. "
United States
Christine T.
The price is HK$1,058
HK$2,126 total
includes taxes & fees
7 Sept - 8 Sept
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
A single-story building with a red door and a garage door.

9. 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 HK$855
HK$2,032 total
includes taxes & fees
5 Oct - 6 Oct
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
A wooden room with two large circular windows, a blue floor, and a wooden bench.

10. 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, (51 reviews)
"The cabin has the most amazing views and the experience was truly incredible! Thanks to Leslie and her family for hosting us."
United States
Gregory P.
The price is HK$1,529
HK$2,193 total
includes taxes & fees
7 Sept - 8 Sept
Sweet New Cabin With Amazing Views Of The Hudson River
A log cabin interior with a fireplace, leather seating, and a ceiling fan.

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is HK$6,155
HK$15,093 total
includes taxes & fees
14 Sept - 15 Sept
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A cabin with a deck, outdoor seating, and a staircase.

12. Gather in 5BR Lodge with Epic View, AC, Near Lakes

Gather in 5BR Lodge with Epic View, AC, Near Lakes
North Creek
10.0 out of 10, Exceptional, (35 reviews)
"We enjoyed our stay here! "
United States
Jeremy H.
The price is HK$3,011
HK$6,553 total
includes taxes & fees
7 Sept - 8 Sept
Gather in 5BR Lodge with Epic View, AC, Near Lakes
A hot tub in a room with wooden walls, two potted plants, and a clock on the wall.

13. 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 HK$2,744
HK$4,430 total
includes taxes & fees
7 Sept - 8 Sept
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
A porch with green railings and red rocking chairs.

14. 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$2,548
HK$4,987 total
includes taxes & fees
30 Sept - 1 Oct
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
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 HK$1,529
HK$3,846 total
includes taxes & fees
29 Sept - 30 Sept
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.

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, (19 reviews)
"The Sagamore Golf house was everything advertised and more! James was a great host and the home was perfect. I recommend this house to anyone looking to visit lake George for a golf trip or just to relax and unwind."
United States
Nicholas F.
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)
"This was our second time staying at Potash Road. Just like the first time, it was a wonderful experience. We will definitely be booking here again."
United States
Laurie S.
The price is HK$1,960
HK$4,454 total
includes taxes & fees
27 Sept - 28 Sept
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
A multi-story house with a dock and boats, surrounded by dense trees.

18. Private Sandy Beach with 125 feet of lake frontage

Private Sandy Beach with 125 feet of lake frontage
Paradox
9.8 out of 10, Exceptional, (28 reviews)
"Great place, great location on the lake with a very short flat walk to the water! Would stay at this house again."
United States
Brandon Y.
The price is HK$3,486
HK$6,960 total
includes taxes & fees
10 Sept - 11 Sept
Private Sandy Beach with 125 feet of lake frontage
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, (47 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is HK$3,136
HK$6,710 total
includes taxes & fees
28 Sept - 29 Sept
Copeland Cabin - Charming Lake House in the Adirondacks
A modern living room with a flat-screen TV, a black entertainment unit, and a 'Welcome to our home' sign.

20. Cozy 3 bedroom house

Cozy 3 bedroom house
South Glens Falls
8.4 out of 10, Very good, (23 reviews)
"Nice place with comfortable beds"
United States
Anonymous traveller
The price is HK$1,164
HK$2,618 total
includes taxes & fees
7 Sept - 8 Sept
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

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"Na"
Jean 2-night trip
Posted less than an hour ago
Lakefront Terrace Resort

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
481
Accommodation
570 Vacation Homes
Lowest Price
HK$1,515
Highest Price
HK$23,537

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