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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chestertown vacation 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 CA $225
CA $639 total
includes taxes & fees
Sep 23 - Sep 24
The Lily Pad at Loon Lake near Gore Mountain
A log cabin interior with a fireplace, leather seating, and a ceiling fan.

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is CA $1,098
CA $2,717 total
includes taxes & fees
Sep 24 - Sep 25
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A hot tub in a room with wooden walls, two potted plants, and a clock on the wall.

3. 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 $491
CA $743 total
includes taxes & fees
Sep 23 - Sep 24
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
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 $262
CA $469 total
includes taxes & fees
Sep 24 - Sep 25
Lovely 3-bedroom house close to Gore Mountain for skiing.
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
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 $120
CA $275 total
includes taxes & fees
Sep 29 - Sep 30
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 $139
CA $325 total
includes taxes & fees
Sep 23 - Sep 24
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.

7. 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)
"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 CA $273
CA $388 total
includes taxes & fees
Sep 24 - Sep 25
Sweet New Cabin With Amazing Views Of The Hudson River
A wooden deck with outdoor furniture, a grill, and a view of a forested area.

8. 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.
The price is CA $2,947
CA $4,970 total
includes taxes & fees
Oct 9 - Oct 10
Sagamore Golf House|Wine Cellar|Movie Theater|15 beds|Hot Tub|Pet Friendly|
A yurt with an open door, surrounded by rocks and trees, under a sunset sky.

9. 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 CA $189
CA $356 total
includes taxes & fees
Oct 11 - Oct 12
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.

10. 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 $236
CA $635 total
includes taxes & fees
Oct 4 - Oct 5
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A cozy outdoor patio area with a fire pit, seating, and a hot tub.

11. CHILLBILLY BOLTON-Cozy & Convenient 3BR/2BA ADK home W/HOT TUB in Bolton Landing

CHILLBILLY BOLTON-Cozy & Convenient 3BR/2BA ADK home W/HOT TUB in Bolton Landing
Bolton Landing
The price is CA $537
CA $1,125 total
includes taxes & fees
Sep 24 - Sep 25
CHILLBILLY BOLTON-Cozy & Convenient 3BR/2BA ADK home W/HOT TUB in Bolton Landing
A compact living space with a wooden ceiling, a sofa, a dining table, and a TV mounted on the wall.

12. 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 $147
CA $356 total
includes taxes & fees
Sep 24 - Sep 25
The Office at North Creek All Season Rental
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 $423
CA $803 total
includes taxes & fees
Oct 5 - Oct 6
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
A white building with a red umbrella, a stone chimney, and a black fence in front.

14. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (86 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 CA $137
CA $269 total
includes taxes & fees
Sep 24 - Sep 25
Adirondack Bungalow Getaway
A single-story house with a porch, a small front yard, and a pathway leading to the entrance.

15. 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 $245
CA $541 total
includes taxes & fees
Sep 26 - Sep 27
Family retreat. 3-br house in serene Bolton Landing. 2 miles to Bolton village.
A swimming pool with a glass ceiling structure, surrounded by chairs and a view of greenery outside.

16. 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 $420
CA $542 total
includes taxes & fees
Oct 1 - Oct 2
Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE
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 $281
CA $707 total
includes taxes & fees
Sep 29 - Sep 30
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.

18. 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 $505
CA $1,131 total
includes taxes & fees
Sep 28 - Sep 29
Copeland Cabin - Charming Lake House in the Adirondacks
A modern kitchen with white cabinets, a dining area with a table set for four, and a living room with a grey sofa and a TV.

19. LAKE GEORGE VILLAGE. 1 Block to BEACH, SHEPHERDS PARK & CANADA St. PET Friendly

LAKE GEORGE VILLAGE. 1 Block to BEACH, SHEPHERDS PARK & CANADA St. PET Friendly
Lake George
9.8 out of 10, Exceptional, (16 reviews)
"Great spot- cute, clean, and close to everything!"
United States
Melinda W.
The price is CA $723
CA $1,407 total
includes taxes & fees
Sep 24 - Sep 25
LAKE GEORGE VILLAGE. 1 Block to BEACH, SHEPHERDS PARK & CANADA St. PET Friendly
A dining area with a large table, chairs, and a view of autumn trees through large windows.

20. Luxurious Lake George Getaway

Luxurious Lake George Getaway
Lake George
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful place, host was awesome in all communications. Great place will be back!"
United States
Wayne E.
The price is CA $598
CA $1,284 total
includes taxes & fees
Sep 30 - Oct 1
Luxurious Lake George Getaway
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

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent
"Very clean, helpful staff, convenient location to the town of LG"
Robert 3-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
295
Accommodation
596 Vacation Homes
Lowest Price
CA $269
Highest Price
CA $4,970

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