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

Chestertown Vacation Rentals

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Check prices for these dates

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

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 CA $214
CA $622 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $126
CA $285 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $141
CA $350 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $283
CA $497 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $141
CA $350 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $150
CA $366 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $192
CA $386 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $1,119
CA $2,769 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $160
CA $529 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $250
CA $572 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $570
CA $895 total
includes taxes & fees
Oct 5 - Oct 6
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
An outdoor seating area with wicker chairs and a wooden bench, overlooking a forested landscape with hills.

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 CA $664
CA $1,496 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $257
CA $365 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 CA $180
CA $569 total
includes taxes & fees
Oct 6 - Oct 7
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A bedroom with a bed, a TV, a desk, a nightstand, a lamp, a ceiling fan, and a view of trees through a window.

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.
The price is CA $597
CA $1,444 total
includes taxes & fees
Oct 30 - Oct 31
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.
The price is CA $2,992
CA $4,933 total
includes taxes & fees
Oct 9 - Oct 10
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 CA $285
CA $713 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $2,100
CA $3,509 total
includes taxes & fees
Oct 9 - Oct 10
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 CA $356
CA $498 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $516
CA $1,151 total
includes taxes & fees
Oct 5 - Oct 6
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

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"Great for families. Pool was great. Coin wash machines a plus. Playground in the back kept kids additionally entertained. Close to Lake George and activities"
Karen 3-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Lake George

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
289
Accommodation
557 Vacation Homes
Lowest Price
CA $285
Highest Price
CA $4,933

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