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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chestertown vacation homes

A bedroom with a large bed, two nightstands, a headboard, and wall-mounted animal decorations.

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 $210
CA $614 total
includes taxes & fees
Oct 29 - Oct 30
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)
"Thank you for an amazing stay. Everything was fantastic! "
United States
Tara F.
The price is CA $139
CA $343 total
includes taxes & fees
Oct 25 - Oct 26
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
A bedroom with a bed, a window with blinds, a wall-mounted TV, and a door.

3. 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 $104
CA $256 total
includes taxes & fees
Oct 25 - Oct 26
Gore MTN & Saratoga ADK Crash Pad! The Cocoon
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 $147
CA $355 total
includes taxes & fees
Oct 25 - Oct 26
The Office at North Creek All Season Rental
A wooden cabin with a porch, wooden furniture, and a view of a forest.

5. 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 $466 total
includes taxes & fees
Oct 25 - Oct 26
Lovely 3-bedroom house close to Gore Mountain for skiing.
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, (26 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
The price is CA $139
CA $343 total
includes taxes & fees
Oct 25 - Oct 26
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
A white building with a red umbrella, a stone chimney, and a black fence in front.

7. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (89 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 $209
CA $362 total
includes taxes & fees
Oct 25 - Oct 26
Adirondack Bungalow Getaway
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 $189
CA $377 total
includes taxes & fees
Oct 25 - Oct 26
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Interior

9. 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 $246
CA $559 total
includes taxes & fees
Oct 26 - Oct 27
Family retreat. 3-br house in serene Bolton Landing. 2 miles to Bolton village.
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 $1,099
CA $2,716 total
includes taxes & fees
Oct 28 - Oct 29
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A cabin with a deck, large windows, and a view of the surrounding landscape.

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 $582
CA $1,431 total
includes taxes & fees
Oct 29 - Oct 30
Gore Mountain Views | Luxury Lodge for 12 | Pets
A porch with green railings and red rocking chairs.

12. 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 $189
CA $553 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.

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, (53 reviews)
"Overall great time"
United States
Dave C.
The price is CA $252
CA $373 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.

14. 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 $560
CA $878 total
includes taxes & fees
Oct 25 - Oct 26
Adirondack Victorian Vacations and Wedding Venue
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 $186
CA $572 total
includes taxes & fees
Oct 25 - Oct 26
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 $522
CA $836 total
includes taxes & fees
Oct 29 - Oct 30
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, (38 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 $448
CA $737 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Upstate Adirondack Cottage Getaway
A spacious living area with a wooden ceiling, a sofa set, a coffee table, and a fireplace.

18. 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 $301
CA $725 total
includes taxes & fees
Oct 26 - Oct 27
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
A modern living room with a flat-screen TV, a black entertainment unit, and a 'Welcome to our home' sign.

19. 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 $231
CA $502 total
includes taxes & fees
Nov 20 - Nov 21
Cozy 3 bedroom house
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 $461
CA $1,072 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

Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Clean. Family friendly"
Emilia 1-night trip
Posted less than an hour ago
Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
423
Accommodation
557 Vacation Homes
Lowest Price
CA $256
Highest Price
CA $2,716

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