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

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chestertown vacation homes

Beach

True Adirondack living. 3-bedroom house in tranquil Diamond Point.

True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Diamond Point
10.0 out of 10, Exceptional, (10 reviews)
"Fantastic stay. Clean and welcoming. Plenty of staples supplied which is always helpful. Will visit again."
United States
Brad S.
The price is ￥96,604
￥163,639 total
includes taxes & fees
Jul 11 - Jul 12
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Property grounds

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 ￥47,606
￥58,440 total
includes taxes & fees
Jul 20 - Jul 21
Waterfront, Pet Friendly Airstream near Lake George in the Adirondack, New York
House, 5 Bedrooms | Exterior

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
The price is ￥37,562
￥131,810 total
includes taxes & fees
Jul 12 - Jul 13
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Interior

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 ￥56,826
￥87,947 total
includes taxes & fees
Jul 11 - Jul 12
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
Property grounds

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 ￥21,919
￥44,032 total
includes taxes & fees
Jul 12 - Jul 13
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Game room

The Office at North Creek All Season Rental

The Office at North Creek All Season Rental
North Creek
8.6 out of 10, Excellent, (12 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 ￥17,697
￥42,423 total
includes taxes & fees
Jul 13 - Jul 14
The Office at North Creek All Season Rental
TV, fireplace

9 Mi to Lake George Village: Home in Queensbury

9 Mi to Lake George Village: Home in Queensbury
Queensbury
9.0 out of 10, Wonderful, (11 reviews)
"Host was very welcoming and was easy to communicate with. Cute home across the street from a park"
United States
Jim A.
9 Mi to Lake George Village: Home in Queensbury
Fridge, microwave, oven, stovetop

Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.

Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
Diamond Point
9.8 out of 10, Exceptional, (59 reviews)
"We enjoyed our trip and the house was very comfortable and clean and well updated."
United States
Nuala D.
The price is ￥89,298
￥154,448 total
includes taxes & fees
Jul 11 - Jul 12
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
Smart TV

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
10.0 out of 10, Exceptional, (14 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 ￥43,025
￥95,251 total
includes taxes & fees
Jul 12 - Jul 13
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
Exterior

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 ￥19,158
￥44,051 total
includes taxes & fees
Jul 12 - Jul 13
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
Smart TV, fireplace, books

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

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Brant Lake
The price is ￥127,453
￥310,744 total
includes taxes & fees
Jul 15 - Jul 16
Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.
Interior

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, (48 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 ￥31,660
￥43,433 total
includes taxes & fees
Jul 12 - Jul 13
Sweet New Cabin With Amazing Views Of The Hudson River
Smart TV, fireplace

Hot Tub • Sauna • 5 Min to Gore Mountain

Hot Tub • Sauna • 5 Min to Gore Mountain
North Creek
9.2 out of 10, Wonderful, (21 reviews)
"Perfect house for our family ski weekend at Gore! We loved the hot tub and plenty of beds and baths for everyone. Great communication with the manager and easy rental experience. Would definitely rent again."
United States
Lisa B.
The price is ￥47,606
￥127,273 total
includes taxes & fees
Jul 14 - Jul 15
Hot Tub • Sauna • 5 Min to Gore Mountain
Interior

The Lake George Village House|EV Charger|King Bed|Outdoor Dining|Walkable

The Lake George Village House|EV Charger|King Bed|Outdoor Dining|Walkable
Lake George
10.0 out of 10, Exceptional, (8 reviews)
"Great property, it was perfect for our weekend attending a wedding. We really enjoyed our stay"
United States
Susan K.
The Lake George Village House|EV Charger|King Bed|Outdoor Dining|Walkable
Outdoor dining

Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (78 reviews)
"Adirondack Bungalow was a very nice place and I would stay again. We are just sorry we didn't have more time to explore the area. Communication with the host was easy and the place was clean and had everything you would have needed to make your stay comfortable."
United States
Gary A.
The price is ￥24,386
￥42,046 total
includes taxes & fees
Aug 5 - Aug 6
Adirondack Bungalow Getaway
Dining

Luxurious Lake George Getaway

Luxurious Lake George Getaway
Lake George
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful place, host was awesome in all communications. Great place will be back!"
United States
Wayne E.
The price is ￥94,981
￥178,238 total
includes taxes & fees
Jul 12 - Jul 13
Luxurious Lake George Getaway
Exterior

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
9.4 out of 10, Exceptional, (21 reviews)
"Had a very nice stay, close to Gore"
United States
Terence M.
The price is ￥20,295
￥45,493 total
includes taxes & fees
Jul 12 - Jul 13
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
Smart TV, fireplace, foosball

Luxury Retreat w Gorgeous Lake Views, Minutes to Marina, Beach & Dining

Luxury Retreat w Gorgeous Lake Views, Minutes to Marina, Beach & Dining
Diamond Point
8.0 out of 10, Very Good, (1 review)
"Host was very good."
United States
Mayura P.
The price is ￥140,279
￥301,327 total
includes taxes & fees
Aug 2 - Aug 3
Luxury Retreat w Gorgeous Lake Views, Minutes to Marina, Beach & Dining
Outdoor dining

Bolton Hill Lodge

Bolton Hill Lodge
Bolton
10.0 out of 10, Exceptional, (8 reviews)
"Awesome stay! Super close to town, spacious rooms, clean and new, comfortable, and lived the outdoor area. No complaints, world stay again!"
United States
Dana B.
The price is ￥161,548
￥282,043 total
includes taxes & fees
Jul 12 - Jul 13
Bolton Hill Lodge
Fridge, microwave, oven, stovetop

River Street - Lake George, Glens Falls

River Street - Lake George, Glens Falls
Warrensburg
8.0 out of 10, Very Good, (2 reviews)
The price is ￥48,546
￥159,651 total
includes taxes & fees
Jul 26 - Jul 27
River Street - Lake George, Glens Falls
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

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"The gentleman at the front desk was great. The room and pool were great. Great stay and looking forward to our return!"
Dan 3-night trip
Posted less than an hour ago
Howard Johnson by Wyndham Lake George

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
227
Accommodation
623 Vacation Homes
Lowest Price
￥42,046
Highest Price
￥310,744