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

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 $617 total
includes taxes & fees
Sep 27 - Sep 28
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
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 $117
CA $273 total
includes taxes & fees
Sep 29 - Sep 30
Gore MTN & Saratoga ADK Crash Pad! The Cocoon
A white building with a red umbrella, a stone chimney, and a black fence in front.

3. 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 $139
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Adirondack Bungalow Getaway
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, (24 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
The price is CA $140
CA $344 total
includes taxes & fees
Sep 27 - Sep 28
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
A cozy living room with a sofa, a television, a fireplace, and a bookshelf.

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 $264
CA $468 total
includes taxes & fees
Sep 28 - Sep 29
Lovely 3-bedroom house close to Gore Mountain for skiing.
A single-story building with a red door and a garage door.

6. 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 compact living space with a wooden ceiling, a sofa, a dining table, and a TV mounted on the wall.

7. 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 $362 total
includes taxes & fees
Sep 29 - Sep 30
The Office at North Creek All Season Rental
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 $191
CA $380 total
includes taxes & fees
Sep 27 - Sep 28
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
A modern kitchen with stainless steel appliances, wooden cabinets, and a window with a view of greenery.

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
The price is CA $248
CA $567 total
includes taxes & fees
Sep 28 - Sep 29
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.

10. 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 $495
CA $794 total
includes taxes & fees
Sep 27 - Sep 28
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
A wooden room with two large circular windows, a blue floor, and a wooden bench.

11. 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 $276
CA $392 total
includes taxes & fees
Sep 27 - Sep 28
Sweet New Cabin With Amazing Views Of The Hudson River
A log cabin interior with a fireplace, leather seating, and a ceiling fan.

12. 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 $2,747 total
includes taxes & fees
Sep 28 - Sep 29
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
A single-story building with a red door and a garage door.

13. 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 $216
CA $606 total
includes taxes & fees
Oct 5 - Oct 6
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A log cabin with a deck, outdoor seating, and a fire pit.

14. 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 $1,485 total
includes taxes & fees
Oct 26 - Oct 27
Gore Mountain Views | Luxury Lodge for 12 | Pets
A porch with green railings and red rocking chairs.

15. 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 $474
CA $923 total
includes taxes & fees
Oct 12 - Oct 13
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
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 $325
CA $765 total
includes taxes & fees
Oct 1 - Oct 2
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.

17. 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 $509
CA $1,140 total
includes taxes & fees
Sep 28 - Sep 29
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.

18. 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 $424
CA $551 total
includes taxes & fees
Sep 27 - Sep 28
Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE
A cabin with a view of a stream and surrounding trees.

19. 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 $354
CA $494 total
includes taxes & fees
Sep 27 - Sep 28
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.

20. Cozy 3 bedroom house

Cozy 3 bedroom house
South Glens Falls
8.4 out of 10, Very good, (23 reviews)
"Nice place and location for visit to Saratoga"
United States
Gilison D.
The price is CA $210
CA $469 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 3 bedroom 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

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

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

8/10 Good
"Breakfast waffles and other offerings were plentiful even though the theme park was closed. Loved the ice cream across the street at Martha’s Dandee Creme"
Elly 1-night trip
Posted 18 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
340
Accommodation
596 Vacation Homes
Lowest Price
CA $273
Highest Price
CA $2,747

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