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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 $630 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 CA $127
CA $283 total
includes taxes & fees
Oct 7 - Oct 8
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 $349 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 $266
CA $471 total
includes taxes & fees
Oct 7 - Oct 8
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 $349 total
includes taxes & fees
Oct 13 - Oct 14
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 $363 total
includes taxes & fees
Oct 7 - Oct 8
The Office at North Creek All Season Rental
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 CA $1,119
CA $2,769 total
includes taxes & fees
Oct 8 - Oct 9
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
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 CA $192
CA $386 total
includes taxes & fees
Oct 12 - Oct 13
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
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 $520 total
includes taxes & fees
Oct 7 - Oct 8
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 $570 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.

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, (32 reviews)
"Our 3rd time staying here and it's always wonderful!"
United States
Blair G.
The price is CA $570
CA $886 total
includes taxes & fees
Oct 13 - Oct 14
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 $659
CA $1,464 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 2 - Nov 3
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 $259
CA $669 total
includes taxes & fees
Oct 13 - Oct 14
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
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 CA $321
CA $752 total
includes taxes & fees
Oct 27 - Oct 28
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, (47 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is CA $512
CA $1,148 total
includes taxes & fees
Oct 19 - Oct 20
Copeland Cabin - Charming Lake House in the Adirondacks
A cabin with a view of a stream and surrounding trees.

17. 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 $501 total
includes taxes & fees
Oct 7 - Oct 8
Three Bedroom House Lake George
A dining area with a large table, chairs, and a view of autumn trees through large windows.

18. 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 CA $700
CA $1,398 total
includes taxes & fees
Oct 7 - Oct 8
Luxurious Lake George Getaway
A lakeside dock with boats, chairs, and a clear view of the lake and mountains.

19. 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 $2,101
CA $3,609 total
includes taxes & fees
Oct 9 - Oct 10
Bolton Beach House|8 beds|Hot Tub|Lake Access|Pet Friendly|
A swimming pool with a glass ceiling structure, surrounded by chairs and a view of greenery outside.

20. Adirondack Retreat Inn & Suites - Premier Rental House

Adirondack Retreat Inn & Suites - Premier Rental House
Lake George
The price is CA $798
CA $1,053 total
includes taxes & fees
Oct 16 - Oct 17
Adirondack Retreat Inn & Suites - Premier 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

The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"The property is quite nice with many amenities. Rooms were clean."
Tracy 1-night trip
Posted 7 hours ago
The Georgian Lakeside Resort

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
264
Accommodation
557 Vacation Homes
Lowest Price
CA $283
Highest Price
CA $3,609

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