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Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Chestertown vacation rentals

Outdoor dining
The Lily Pad at Loon Lake near Gore Mountain

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, (39 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is ￥28,603
￥76,480 total
includes taxes & fees
Jan 15 - Jan 16
The Lily Pad at Loon Lake near Gore Mountain
Interior
Rustic Adirondack Retreat on Tripp Lake

Rustic Adirondack Retreat on Tripp Lake

Rustic Adirondack Retreat on Tripp Lake
Chestertown
10.0 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay, the condo was very clean and beautifully decorated. The beds and couches were very comfortable and location was perfect with a local beach and lake and in driving distance to great restaurants and Lake George. Definitely recommend Linda’s property for your next vacation. "
United States
Natercia R.
The price is ￥39,508
￥85,251 total
includes taxes & fees
Jan 16 - Jan 17
Rustic Adirondack Retreat on Tripp Lake
Exterior
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (113 reviews)
"Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion. "
United States
Kathy B.
The price is ￥47,760
￥121,224 total
includes taxes & fees
Feb 4 - Feb 5
Eagles Nest at Loon Lake near Gore Mountain
Smart TV
Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
The price is ￥64,002
￥101,213 total
includes taxes & fees
Jan 19 - Jan 20
Authentic Log Cabin with Lake Views and Sauna
Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, individually decorated
Trout House Village Resort

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (21 reviews)
"Great updated cabin. "
United States
Diane
The price is ￥23,644
￥30,197 total
includes taxes & fees
Jan 20 - Jan 21
Trout House Village Resort
Property grounds
Three Bedroom House Lake George

Three Bedroom House Lake George

Three Bedroom House Lake George
Lake George
8.0 out of 10, Very Good, (1 review)
"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 ￥19,754
￥31,224 total
includes taxes & fees
Jan 19 - Jan 20
Three Bedroom House Lake George
Smart TV
Riverbend Cabin - Wonderful 2-bedroom home

Riverbend Cabin - Wonderful 2-bedroom home

Riverbend Cabin - Wonderful 2-bedroom home
2.0 star property
Hadley
The price is ￥15,803
￥49,716 total
includes taxes & fees
Jan 15 - Jan 16
Riverbend Cabin - Wonderful 2-bedroom home
Dining
Luxury Cabin Sleeps 4 to 7 - mins to Lake George

Luxury Cabin Sleeps 4 to 7 - mins to Lake George

Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Lake Luzerne
10.0 out of 10, Exceptional, (8 reviews)
"Awesome visit, everything as described!"
United States
Adam H.
The price is ￥31,606
￥84,944 total
includes taxes & fees
Jan 19 - Jan 20
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Property grounds
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access

The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access

The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
2.0 star property
Hadley
The price is ￥26,312
￥37,463 total
includes taxes & fees
Jan 19 - Jan 20
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
Terrace/patio
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Lake George
10.0 out of 10, Exceptional, (16 reviews)
"What a wonderful home away from home for the weekend! Cabin was exactly as described, extremely clean and welcoming. Host were very professional and kind. We definitely will be back"
United States
Taina R.
The price is ￥26,312
￥65,518 total
includes taxes & fees
Jan 19 - Jan 20
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Terrace/patio
Little Black Aframe by the Brook- 5m to Waterfall

Little Black Aframe by the Brook- 5m to Waterfall

Little Black Aframe by the Brook- 5m to Waterfall
Warrensburg
9.0 out of 10, Wonderful, (7 reviews)
"My wife and I had a great time. We would stay here again. Great communication with the host. Thanks!"
United States
Ted D.
The price is ￥16,549
￥33,391 total
includes taxes & fees
Jan 15 - Jan 16
Little Black Aframe by the Brook- 5m to Waterfall
Interior
Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
9.6 out of 10, Exceptional, (60 reviews)
"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 ￥23,705
￥35,083 total
includes taxes & fees
Jan 15 - Jan 16
Beautiful cottage on scenic Adirondack hobby farm
Outdoor dining
Adirondack Bungalow Getaway

Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
10.0 out of 10, Exceptional, (69 reviews)
"Great spot "
United States
Winter R.
The price is ￥15,503
￥30,713 total
includes taxes & fees
Jan 19 - Jan 20
Adirondack Bungalow Getaway
Property grounds
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
North River
10.0 out of 10, Exceptional, (95 reviews)
"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 ￥26,075
￥36,837 total
includes taxes & fees
Jan 15 - Jan 16
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
Interior
Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin
Indian Lake
10.0 out of 10, Exceptional, (1 review)
The price is ￥29,038
￥59,522 total
includes taxes & fees
Feb 2 - Feb 3
Beach - Family & Pet Friendly - Adirondack Cabin
Outdoor dining
Gore Mountain Lift View: North Creek Main St Apt 2

Gore Mountain Lift View: North Creek Main St Apt 2

Gore Mountain Lift View: North Creek Main St Apt 2
North Creek
9.0 out of 10, Wonderful, (10 reviews)
"Great location… Enjoyed our stay"
United States
Lynda N.
The price is ￥31,606
￥60,113 total
includes taxes & fees
Jan 19 - Jan 20
Gore Mountain Lift View: North Creek Main St Apt 2
Interior
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
North River
9.2 out of 10, Wonderful, (64 reviews)
"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 ￥27,655
￥42,099 total
includes taxes & fees
Jan 15 - Jan 16
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
Property grounds
Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
10.0 out of 10, Exceptional, (2 reviews)
"Simple mountain cabin in remote location. Space in great for a couple or two singles. Property has plenty of elbow room with several other structures spread out across a giant clearing next to a lake. We hiked, swam, kayaked, fished and relaxed and enjoyed the views. We cooked dinner on the charcoal grill, and drank our morning coffee while listening to the birds. Hosts were attentive and chatted with us a few times. "
United States
Kerstin Y.
The price is ￥25,910
￥55,149 total
includes taxes & fees
Feb 8 - Feb 9
Lakefront-Family & Pet Friendly-Adirondack Cabin
Property grounds
Gorgeous Mountain Top Cabin with Beautiful Views

Gorgeous Mountain Top Cabin with Beautiful Views

Gorgeous Mountain Top Cabin with Beautiful Views
North River
10.0 out of 10, Exceptional, (35 reviews)
"The cabin has everything you need in a small space, yet comfortable. The setting and views from it really cannot be beat!"
United States
Austin M.
The price is ￥26,075
￥37,889 total
includes taxes & fees
Jan 19 - Jan 20
Gorgeous Mountain Top Cabin with Beautiful Views
Exterior
Rustic Vacation Rental for Couples near Hoffman Notch, New York

Rustic Vacation Rental for Couples near Hoffman Notch, New York

Rustic Vacation Rental for Couples near Hoffman Notch, New York
2.0 star property
Schroon Lake
The price is ￥19,991
￥26,562 total
includes taxes & fees
Jan 17 - Jan 18
Rustic Vacation Rental for Couples near Hoffman Notch, New York
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

Home2 Suites by Hilton Queensbury Lake George

Home2 Suites by Hilton Queensbury Lake George

10/10 Excellent
"We arrived half an hour early before the check in and our room was ready. Staff was really friendly. Wide variety of selections for break fast, the lady who is in charge was very sweet and attentive."
Judith 2-night trip
Posted 1 day ago
Home2 Suites by Hilton Queensbury Lake George

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 vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

What are some of the best vacation home rentals in Chestertown?

Eagles Nest at Loon Lake near Gore Mountain: This highly rated vacation home rental in Chestertown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Chestertown?

With 57 Expedia vacation rentals, you're sure 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 vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.