Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Chestertown holiday homes

Outdoor dining

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, (41 reviews)
"The house is very clean and there was no shortage of fresh towels. "
United States
Sophia H.
The price is €384
includes taxes & fees
9 Jun - 10 Jun
The Lily Pad at Loon Lake near Gore Mountain
Exterior

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (118 reviews)
"Great house. Great location"
United States
David S.
The price is €598
includes taxes & fees
10 Jun - 11 Jun
Eagles Nest at Loon Lake near Gore Mountain
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 €251
includes taxes & fees
3 Jun - 4 Jun
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
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, (13 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 €430
includes taxes & fees
3 Jun - 4 Jun
Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces
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)
"Great for a ski trip to gore mountain!"
United States
Ryan H.
The price is €233
includes taxes & fees
9 Jun - 10 Jun
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
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 €195
includes taxes & fees
3 Jun - 4 Jun
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
Dining

Gorgeous Yurt in the Adirondacks for a Unique Glamping Getaway near Minerva, New York

Gorgeous Yurt in the Adirondacks for a Unique Glamping Getaway near Minerva, New York
Minerva
The price is €229
includes taxes & fees
3 Jun - 4 Jun
Gorgeous Yurt in the Adirondacks for a Unique Glamping Getaway near Minerva, New York
Property grounds

Lovely 3-bedroom house close to Gore Mountain for skiing.

Lovely 3-bedroom house close to Gore Mountain for skiing.
North Creek
10.0 out of 10, Exceptional, (2 reviews)
"Very cute and cozy / responsive and helpful host"
United States
Renee B.
The price is €284
includes taxes & fees
4 Jun - 5 Jun
Lovely 3-bedroom house close to Gore Mountain for skiing.
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 €726
includes taxes & fees
7 Jun - 8 Jun
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
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, (46 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 €241
includes taxes & fees
3 Jun - 4 Jun
Sweet New Cabin With Amazing Views Of The Hudson River
Exterior

Rustic Vacation Rental for Couples near Hoffman Notch, New York

Rustic Vacation Rental for Couples near Hoffman Notch, New York
Schroon Lake
9.0 out of 10, Wonderful, (2 reviews)
"Host was so sweet! Looking forward to staying here again"
United States
Bre Z.
The price is €146
includes taxes & fees
4 Jun - 5 Jun
Rustic Vacation Rental for Couples near Hoffman Notch, New York
Games 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 €199
includes taxes & fees
3 Jun - 4 Jun
The Office at North Creek All Season Rental
Outdoor dining

Secluded, Dog Friendly Tiny House on the Hudson River, near Saratoga Springs

Secluded, Dog Friendly Tiny House on the Hudson River, near Saratoga Springs
Corinth
The price is €536
includes taxes & fees
2 Jul - 3 Jul
Secluded, Dog Friendly Tiny House on the Hudson River, near Saratoga Springs
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, (9 reviews)
"Fantastic stay. Clean and welcoming. Plenty of staples supplied which is always helpful. Will visit again."
United States
Brad S.
The price is €871
includes taxes & fees
3 Jun - 4 Jun
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
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
10.0 out of 10, Exceptional, (58 reviews)
"We enjoyed our trip and the house was very comfortable and clean and well updated."
United States
Nuala D.
The price is €812
includes taxes & fees
3 Jun - 4 Jun
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
TV, DVD player

Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!
bolton landing
9.2 out of 10, Wonderful, (112 reviews)
"the host was great to work with and house was perfect! "
United States
jamie o.
Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!
Exterior

NEW! 10 Mi to Gore Mountain: Home in Adirondack Park

NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
Olmstedville
10.0 out of 10, Exceptional, (8 reviews)
"Exactly what we needed & was stocked with great games, cooking supplies & blankets! Can’t wait to come back."
United States
Katlyn H.
The price is €686
includes taxes & fees
4 Jun - 5 Jun
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
Bathtub, hair dryer, towels, shampoo

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 €398
includes taxes & fees
4 Jun - 5 Jun
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
A heated pool

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 €545
includes taxes & fees
3 Jun - 4 Jun
Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE
Interior

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
10.0 out of 10, Exceptional, (9 reviews)
"Great spot- cute, clean, and close to everything!"
United States
Melinda W.
The price is €981
includes taxes & fees
23 Jun - 24 Jun
LAKE GEORGE VILLAGE. 1 Block to BEACH, SHEPHERDS PARK & CANADA St. PET Friendly
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

Lodge at Schroon Lake

Lodge at Schroon Lake

10/10 Excellent
"Wonderful location, beautiful resort. The pool was incredible. There are no showers however so come prepared. Do not shower and change after you have finished swimming. The cookies when you check in are over the top delicious. So don’t have dessert before you come. All the little touches are wonderful, including the water with fruit at check-in. The staff was incredible and so also so helpful. My two granddaughters had a wonderful time. The room was very comfortable, the bedding was lovely. I would definitely stay here again and recommend it. The daily experience, the Swan, was wonderful and all of the staff there were fantastic."
Lisa 1-night trip
Posted 2 hours ago
Lodge at Schroon Lake

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
Accommodation
562 Holiday Homes
Lowest Price
€726
Highest Price
€726