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 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 CA $212
CA $622 total
includes taxes & fees
Oct 20 - Oct 21
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 $132
CA $290 total
includes taxes & fees
Nov 15 - Nov 16
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 $140
CA $344 total
includes taxes & fees
Oct 19 - Oct 20
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
A single-story building with a red door and a garage door.

4. 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, (25 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
The price is CA $140
CA $344 total
includes taxes & fees
Oct 19 - Oct 20
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.

5. 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 $148
CA $363 total
includes taxes & fees
Oct 19 - Oct 20
The Office at North Creek All Season Rental
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 CA $264
CA $469 total
includes taxes & fees
Oct 19 - Oct 20
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.

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 $191
CA $384 total
includes taxes & fees
Oct 19 - Oct 20
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
A white building with a red umbrella, a stone chimney, and a black fence in front.

8. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (88 reviews)
"Quiet surroundings and quiet neighbors makes for a restful vacation spot, close to many nature trails and lakes and rivers."
United States
Diana D.
The price is CA $211
CA $366 total
includes taxes & fees
Oct 19 - Oct 20
Adirondack Bungalow Getaway
An outdoor seating area with wicker chairs and a wooden bench, overlooking a forested landscape with hills.

9. 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 $526
CA $1,334 total
includes taxes & fees
Nov 9 - Nov 10
Gore Mountain Views | Luxury Lodge for 12 | Pets
A log cabin interior with a fireplace, leather seating, and a ceiling fan.

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is CA $1,110
CA $2,743 total
includes taxes & fees
Oct 19 - Oct 20
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A bedroom with a bed, a nightstand, a window, and wooden walls.

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, (2 reviews)
"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 CA $248
CA $569 total
includes taxes & fees
Oct 19 - Oct 20
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. Adirondack Victorian Vacations and Wedding Venue

Adirondack Victorian Vacations and Wedding Venue
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 $566
CA $876 total
includes taxes & fees
Oct 19 - Oct 20
Adirondack Victorian Vacations and Wedding Venue
A porch with green railings and red rocking chairs.

13. 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 $191
CA $565 total
includes taxes & fees
Oct 27 - Oct 28
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
A wooden room with two large circular windows, a blue floor, and a wooden bench.

14. 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 $255
CA $369 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.

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 CA $197
CA $585 total
includes taxes & fees
Oct 19 - Oct 20
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A two-story wooden house with a covered porch and a staircase leading to the upper level.

16. Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
Warrensburg
9.8 out of 10, Exceptional, (63 reviews)
"House was great, experience was even better. Laney was a tremendous host."
United States
Brandon M.
The price is CA $527
CA $849 total
includes taxes & fees
Oct 19 - Oct 20
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge
An outdoor seating area with four chairs and a square table with a fire pit.

17. Cozy Upstate Adirondack Cottage Getaway

Cozy Upstate Adirondack Cottage Getaway
Warrensburg
9.8 out of 10, Exceptional, (37 reviews)
"Property was very clean. Plenty of room for family of eight. My only complaint is the beds were extremely soft for me. Would consider staying again."
United States
Robin M.
The price is CA $453
CA $753 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Upstate Adirondack Cottage Getaway
A wooden deck with outdoor furniture, a grill, and a view of a forested area.

18. 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.
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.

19. 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 $311
CA $751 total
includes taxes & fees
Oct 19 - Oct 20
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.

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, (48 reviews)
"Extremely charming house! Perfect for a quiet get away!"
United States
Halley S.
The price is CA $465
CA $1,083 total
includes taxes & fees
Nov 8 - Nov 9
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

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"I have stayed at this place many times and will stay there again. Every time I’ve stayed there I’ve enjoyed my stay. Room is always clean and the people that work there are always nice. Easy walk into the center of town."
doug 2-night trip
Posted 2 hours ago
Adirondack Retreat Inn & Suites

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
440
Accommodation
557 Vacation Homes
Lowest Price
CA $300
Highest Price
CA $2,743

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