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Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Holiday Rentals in Chestertown

Outdoor dining
The Lily Pad at Loon Lake near Gore Mountain

Holiday Home in Chestertown

9.6 out of 10, Exceptional, (39)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is HK$1,175
HK$3,463 total
includes taxes & fees
10 Dec - 11 Dec
The Lily Pad at Loon Lake near Gore Mountain
Interior
Authentic Log Cabin with Lake Views and Sauna

Cabin in Chestertown

The price is HK$2,102
HK$3,655 total
includes taxes & fees
10 Dec - 11 Dec
Authentic Log Cabin with Lake Views and Sauna
Living area
Trout House Village Resort

Cabin in Hague

3.0 star property
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
The price is HK$1,164
HK$1,487 total
includes taxes & fees
17 Dec - 18 Dec
Trout House Village Resort
Fridge, microwave, oven, stovetop
Riverbend Cabin - Wonderful 2-bedroom home

Cabin in Hadley

2.0 star property
The price is HK$778
HK$2,336 total
includes taxes & fees
6 Jan - 7 Jan 2026
Riverbend Cabin - Wonderful 2-bedroom home
Outdoor dining
Gore Mountain Lift View: North Creek Main St Apt 2

Apartment in North Creek

9.0 out of 10, Wonderful, (10)
"Great location… Enjoyed our stay"
United States
Lynda N.
The price is HK$778
HK$1,985 total
includes taxes & fees
12 Dec - 13 Dec
Gore Mountain Lift View: North Creek Main St Apt 2
Interior
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

Cottage in Hudson Falls

3.0 star property
The price is HK$1,906
HK$5,259 total
includes taxes & fees
23 Dec - 24 Dec
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
Property grounds
Three Bedroom House Lake George

Holiday Home in Lake George

8.0 out of 10, Very good, (1)
"This is a neat, small house, that while a bit dated in decor, was very comfortable and clean for an overnight reunion of "senior" friends from high school. It provided us with the space to sit and reminisce and catch up on each other's lives. There was a nice deck overlooking a small picturesque stream, a large, comfortable living room and an adequate kitchen that met our needs. There is also a pool, which, being late in September was not open, but is a nice bonus in season, as well as an...
United States
Susan T.
The price is HK$973
HK$1,529 total
includes taxes & fees
6 Jan - 7 Jan 2026
Three Bedroom House Lake George
Interior
Beautiful cottage on scenic Adirondack hobby farm

Cabin in North River

9.6 out of 10, Exceptional, (60)
"This place was great! We enjoyed walking the property and hot tubbing. The farmhouse was unique, but amazing! Leslie and team were friendly, we enjoyed chats over breakfast and pizza. Would definitely visit again."
United States
Jake W.
The price is HK$1,167
HK$1,727 total
includes taxes & fees
10 Dec - 11 Dec
Beautiful cottage on scenic Adirondack hobby farm
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

Cabin in North River

10.0 out of 10, Exceptional, (93)
"Cabin was very well done, clean- bed was super comfortable! The view of the mountains was fantastic- great for star watching too!"
United States
millie h.
The price is HK$1,284
HK$1,865 total
includes taxes & fees
16 Dec - 17 Dec
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Property grounds
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access

Cottage in Hadley

2.0 star property
The price is HK$1,152
HK$1,623 total
includes taxes & fees
10 Dec - 11 Dec
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
Exterior
Gore Mountain Lift View: Wade St. Apt 2

Holiday Home in North Creek

9.4 out of 10, Exceptional, (12)
"Thank you for an amazing stay. Everything was fantastic! "
United States
Tara F.
The price is HK$778
HK$1,986 total
includes taxes & fees
10 Dec - 11 Dec
Gore Mountain Lift View: Wade St. Apt 2
Exterior
Adirondack Bungalow Getaway

Holiday Home in Warrensburg

10.0 out of 10, Exceptional, (67)
"Great spot "
United States
Winter R.
The price is HK$763
HK$1,512 total
includes taxes & fees
10 Dec - 11 Dec
Adirondack Bungalow Getaway
Interior
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

Cabin in North River

9.2 out of 10, Wonderful, (63)
"See you next year amazing stay great food loved the bird camp cabin—- Brian, Darlene, Gracie and Hayden "
United States
Brian W.
The price is HK$1,362
HK$2,073 total
includes taxes & fees
10 Dec - 11 Dec
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR
Interior
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park

Holiday Home in Olmstedville

10.0 out of 10, Exceptional, (8)
"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 HK$1,886
HK$5,873 total
includes taxes & fees
10 Dec - 11 Dec
NEW! 10 Mi to Gore Mountain: Home in Adirondack Park
Dining
Luxury Cabin Sleeps 4 to 7 - mins to Lake George

Cabin in Lake Luzerne

10.0 out of 10, Exceptional, (7)
"Cabin was great! It was nice and secluded, but at the same time clean and modern. Plenty of place for the kids to spread out and also enjoy family dinners together. Hot tub and firepit were a nice touch."
United States
Joel B.
The price is HK$1,167
HK$3,400 total
includes taxes & fees
11 Dec - 12 Dec
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Exterior
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Cottage in Fort Ann

10.0 out of 10, Exceptional, (24)
"Great little get away with the family and the dogs! Met both Linda and her husband. Both very friendly and accommodating "
United States
Allan G.
The price is HK$1,499
HK$2,978 total
includes taxes & fees
14 Dec - 15 Dec
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Interior
Huge Windows Downtown 2Bd Apt w/ Main Strip Access

Apartment in Glens Falls

10.0 out of 10, Exceptional, (2)
"Great location with rustic touches and fully renovated"
United States
Brian H.
The price is HK$2,334
HK$4,197 total
includes taxes & fees
8 Jan - 9 Jan 2026
Huge Windows Downtown 2Bd Apt w/ Main Strip Access
Exterior
Lake Escape- Cozy 4 bedroom retreat in Lake George

Holiday Home in Lake George

9.6 out of 10, Exceptional, (8)
"Really cozy home very close to town. Clean and ready on time. Great place to stay!"
United States
Adam F.
The price is HK$1,493
HK$3,395 total
includes taxes & fees
10 Dec - 11 Dec
Lake Escape- Cozy 4 bedroom retreat in Lake George
Outdoor dining
Gorgeous mountain views and private!

Cabin in North River

10.0 out of 10, Exceptional, (35)
"We enjoyed our stay very much. A little slice of heaven. "
United States
Kelly
The price is HK$1,168
HK$1,728 total
includes taxes & fees
10 Dec - 11 Dec
Gorgeous mountain views and private!
Outdoor dining
Camp Lillian Gorgeous New Cabin with Mountain Views

Cabin in North River

9.8 out of 10, Exceptional, (77)
"Just what we were looking for. Beautiful and peaceful. "
United States
Lisa S.
The price is HK$1,284
HK$1,874 total
includes taxes & fees
15 Dec - 16 Dec
Camp Lillian Gorgeous New Cabin with Mountain Views
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
"Yes, will be coming back "
Marc 1-night trip
Posted 2 days ago
Six Flags Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Terrace on the Lake – Private Lakefront with Breathtaking Views: This holiday home rental outside of Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chestertown?

With 58 Expedia holiday rentals, you're guaranteed to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.