A waterfront town with a pier, dock, and several buildings.

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chestertown vacation homes

Exterior

1. 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 ￥20,137
￥44,780 total
includes taxes & fees
Aug 12 - Aug 13
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
Game room

2. 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 ￥21,396
￥46,520 total
includes taxes & fees
Aug 12 - Aug 13
The Office at North Creek All Season Rental
Exterior

3. 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, (22 reviews)
"Had a very nice stay, close to Gore"
United States
Terence M.
The price is ￥17,620
￥41,462 total
includes taxes & fees
Aug 10 - Aug 11
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
Property grounds

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 ￥31,960
￥56,082 total
includes taxes & fees
Sep 3 - Sep 4
Lovely 3-bedroom house close to Gore Mountain for skiing.
Exterior

5. 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 ￥21,238
￥42,665 total
includes taxes & fees
Aug 6 - Aug 7
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Outdoor dining

6. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (81 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.
Adirondack Bungalow Getaway
Interior

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, (49 reviews)
"Fab cabin and loved the Japanese hot tub. Close to restaurants short drive and also close to gore mountain. We loved our stay!! "
United States
Ashling
The price is ￥30,677
￥44,005 total
includes taxes & fees
Aug 13 - Aug 14
Sweet New Cabin With Amazing Views Of The Hudson River
Interior

8. 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 ￥55,062
￥88,884 total
includes taxes & fees
Aug 6 - Aug 7
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
Smart TV, fireplace, books

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is ￥123,496
￥303,019 total
includes taxes & fees
Aug 6 - Aug 7
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Exterior

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, (2 reviews)
"This is a wonderful location. We thoroughly enjoyed the town of North Creek!"
United States
Jane H W.
The price is ￥42,791
￥92,528 total
includes taxes & fees
Sep 1 - Sep 2
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
Smart TV

11. 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, (16 reviews)
"This was our second time staying at Potash Road. Just like the first time, it was a wonderful experience. We will definitely be booking here again."
United States
Laurie S.
The price is ￥42,476
￥93,327 total
includes taxes & fees
Aug 30 - Aug 31
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
TV, fireplace

12. La Bella Vita in Bolton Landing

La Bella Vita in Bolton Landing
Bolton Landing
9.6 out of 10, Exceptional, (17 reviews)
"The place was great and the view of the lake was wonderful to wake up to 10 out of 10 will be back next year"
United States
Michael Y.
La Bella Vita in Bolton Landing
Property grounds

13. 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 ￥39,330
￥55,880 total
includes taxes & fees
Sep 2 - Sep 3
Three Bedroom House Lake George
Miscellaneous

14. Waterfront, Pet Friendly Airstream near Lake George in the Adirondack, New York

Waterfront, Pet Friendly Airstream near Lake George in the Adirondack, New York
Corinth
The price is ￥46,328
￥56,685 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront, Pet Friendly Airstream near Lake George in the Adirondack, New York
A heated pool

15. 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 ￥76,300
￥100,655 total
includes taxes & fees
Aug 24 - Aug 25
Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE
Property grounds

16. Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.

Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.
Corinth
10.0 out of 10, Exceptional, (35 reviews)
"The host was incredibly friendly and accommodating. The cabin was stocked with everything you could need and perfect for a cozy, fun weekend getaway right on the water!"
United States
Sarah G.
The price is ￥70,794
￥107,292 total
includes taxes & fees
Aug 6 - Aug 7
Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.
Interior

17. Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls

Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
Glens Falls
10.0 out of 10, Exceptional, (7 reviews)
"Our stay was excellent!"
United States
Amanda S.
The price is ￥86,526
￥144,593 total
includes taxes & fees
Aug 23 - Aug 24
Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
Property grounds

18. Lakeshore Cottage- Family and Pet Friendly, Lakefront, Fireplace, and Gameroom

Lakeshore Cottage- Family and Pet Friendly, Lakefront, Fireplace, and Gameroom
Fort Ann
9.8 out of 10, Exceptional, (30 reviews)
"The lake was great, the game room was the best part"
United States
dylan c.
The price is ￥313,853
￥397,970 total
includes taxes & fees
Aug 21 - Aug 22
Lakeshore Cottage- Family and Pet Friendly, Lakefront, Fireplace, and Gameroom
Fridge, microwave, dishwasher, cookware/dishes/utensils

19. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

Gore MTN & Saratoga ADK Crash Pad! The Cocoon
Warrensburg
The price is ￥19,114
￥38,156 total
includes taxes & fees
Aug 9 - Aug 10
Gore MTN & Saratoga ADK Crash Pad! The Cocoon
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

Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Property was great. It wasn’t overpacked with people. Water park is small but for 4 year olds they love it."
Nicole 1-night trip
Posted less than an hour ago
Six Flags Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
276
Accommodation
623 Vacation Homes
Lowest Price
￥38,156
Highest Price
￥397,970