Holiday Homes in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 June - 21 June
In two months
31 July - 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 AU$619
includes taxes & fees
9 June - 10 June
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 AU$962
includes taxes & fees
3 June - 4 June
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 AU$407
includes taxes & fees
6 June - 7 June
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
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 AU$308
includes taxes & fees
3 June - 4 June
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
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 AU$1,135
includes taxes & fees
9 June - 10 June
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
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 AU$717
includes taxes & fees
3 June - 4 June
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 AU$378
includes taxes & fees
9 June - 10 June
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
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 AU$233
includes taxes & fees
4 June - 5 June
Rustic Vacation Rental for Couples near Hoffman Notch, New York
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 AU$369
includes taxes & fees
6 June - 7 June
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 AU$468
includes taxes & fees
4 June - 5 June
Lovely 3-bedroom house close to Gore Mountain for skiing.
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 AU$390
includes taxes & fees
3 June - 4 June
Sweet New Cabin With Amazing Views Of The Hudson River
Smart TV

3BR Retreat w/ Game Room, Hot Tub Near Lake George

3BR Retreat w/ Game Room, Hot Tub Near Lake George
Lake Luzerne
10.0 out of 10, Exceptional, (3 reviews)
"All was good. Hot tub stayed a little cool. "
United States
leah c.
The price is AU$1,105
includes taxes & fees
3 June - 4 June
3BR Retreat w/ Game Room, Hot Tub Near Lake George
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 AU$325
includes taxes & fees
3 June - 4 June
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 AU$599
includes taxes & fees
7 June - 8 June
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 AU$1,378
includes taxes & fees
3 June - 4 June
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 AU$1,192
includes taxes & fees
15 June - 16 June
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.
The price is AU$484
includes taxes & fees
3 June - 4 June
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 AU$1,112
includes taxes & fees
3 June - 4 June
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
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 AU$880
includes taxes & fees
3 June - 4 June
Adirondack Retreat Inn & Suites - TOWNHOUSE RENTAL HOUSE
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 AU$649
includes taxes & fees
4 June - 5 June
6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

The Georgian Lakeside Resort

The Georgian Lakeside Resort

10/10 Excellent
"We thoroughly enjoyed our stay. I was traveling with two teen granddaughters. We had a problem with the hot water and we had an immediate response from the front desk and then an immediate response from the maintenance. The next morning, the hot water again didn’t work so I think this is just a beginning of the season glitch and I’m sure we’ll be fixed. Otherwise, everything about this day was wonderful. Was the chef, Antonio, was fantastic, as was Eugene, with the Wait staff"
Lisa 1-night trip
Posted 11 hours ago
The Georgian Lakeside Resort

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
286
Accommodation
552 Holiday Homes
Lowest Price
AU$233
Highest Price
AU$1,378