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 $213
CA $620 total
includes taxes & fees
Oct 15 - Oct 16
The Lily Pad at Loon Lake near Gore Mountain
A single-story building with a red door and a garage door.

2. 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 $351 total
includes taxes & fees
Oct 12 - Oct 13
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.

3. 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 $474 total
includes taxes & fees
Oct 14 - Oct 15
Lovely 3-bedroom house close to Gore Mountain for skiing.
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 CA $149
CA $365 total
includes taxes & fees
Oct 12 - Oct 13
The Office at North Creek All Season Rental
A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

5. 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 $128
CA $289 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.

6. 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 $351 total
includes taxes & fees
Oct 12 - Oct 13
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
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 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.

8. 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 $528 total
includes taxes & fees
Oct 12 - Oct 13
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
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 CA $1,117
CA $2,759 total
includes taxes & fees
Oct 12 - Oct 13
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
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
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 CA $250
CA $571 total
includes taxes & fees
Oct 12 - Oct 13
Family retreat. 3-br house in serene Bolton Landing. 2 miles to Bolton village.
An outdoor seating area with wicker chairs and a wooden bench, overlooking a forested landscape with hills.

11. 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 $500
CA $8,464 total
includes taxes & fees
Oct 28 - Oct 29
Gore Mountain Views | Luxury Lodge for 12 | Pets
A wooden room with two large circular windows, a blue floor, and a wooden bench.

12. 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 $256
CA $369 total
includes taxes & fees
Nov 1 - Nov 2
Sweet New Cabin With Amazing Views Of The Hudson River
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, (32 reviews)
"Our 3rd time staying here and it's always wonderful!"
United States
Blair G.
The price is CA $569
CA $894 total
includes taxes & fees
Oct 12 - Oct 13
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
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 $210
CA $606 total
includes taxes & fees
Oct 13 - Oct 14
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)
"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 $3,294
CA $5,319 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 CA $314
CA $743 total
includes taxes & fees
Nov 1 - Nov 2
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
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 $504 total
includes taxes & fees
Oct 12 - Oct 13
Three Bedroom House Lake George
A modern living room with a flat-screen TV, a black entertainment unit, and a 'Welcome to our home' sign.

18. Cozy 3 bedroom house

Cozy 3 bedroom house
South Glens Falls
8.4 out of 10, Very good, (25 reviews)
"Nice place and location for visit to Saratoga"
United States
Gilison D.
The price is CA $211
CA $478 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 3 bedroom house
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 CA $469
CA $1,090 total
includes taxes & fees
Nov 8 - Nov 9
Copeland Cabin - Charming Lake House in the Adirondacks
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 CA $569
CA $747 total
includes taxes & fees
Oct 12 - Oct 13
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

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

8/10 Good
"Breakfast wasn’t very good"
Robert 1-night trip
Posted 10 hours ago
Baymont by Wyndham Queensbury / Lake George

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
254
Accommodation
557 Vacation Homes
Lowest Price
CA $289
Highest Price
CA $8,464

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