Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Chestertown holiday rentals

Smart TV

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this property. Everything was very clean and well kept. The pictures shown on the listing are accurate, and it’s even better once you’re in. The couch is really comfortable, as well as the beds. The host is very responsive and willing to properly address any concerns/questions you may have. Would highly recommend."
United States
Eliyahu N.
The price is HK$1,763
HK$2,235 total
includes taxes & fees
28 Apr - 29 Apr
Authentic Log Cabin with Lake Views and Sauna
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 HK$1,175
HK$3,462 total
includes taxes & fees
28 Apr - 29 Apr
The Lily Pad at Loon Lake near Gore Mountain
Egyptian cotton sheets, premium bedding, individually decorated

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (22 reviews)
"spotless room w an incredible view!"
United States
Joanne
The price is HK$1,510
HK$1,872 total
includes taxes & fees
20 May - 21 May
Trout House Village Resort
Property grounds

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, (99 reviews)
"Perfectly cozy, and just right for me and my tiny dog to get away for a few days!"
United States
Bobby R.
The price is HK$1,058
HK$1,583 total
includes taxes & fees
29 Apr - 30 Apr
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
Interior

< 1 Mi to Boat Launch! Schroon Lake Basecamp

< 1 Mi to Boat Launch! Schroon Lake Basecamp
3.0 star property
Schroon Lake
The price is HK$674
HK$1,276 total
includes taxes & fees
28 Apr - 29 Apr
< 1 Mi to Boat Launch! Schroon Lake Basecamp
Property grounds

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Hadley
10.0 out of 10, Exceptional, (23 reviews)
"Perfect remote location for a weekend away! Jackie is a great host and cabin was very clean and delicate. "
United States
Hanna D.
The price is HK$1,269
HK$1,741 total
includes taxes & fees
29 Apr - 30 Apr
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Terrace/patio

Little Black Aframe by the Brook- 5m to Waterfall

Little Black Aframe by the Brook- 5m to Waterfall
Warrensburg
9.2 out of 10, Wonderful, (9 reviews)
"Cabin was super cozy and relaxing in a remote location. Perfect getaway "
United States
Blaine M.
The price is HK$838
HK$1,687 total
includes taxes & fees
28 Apr - 29 Apr
Little Black Aframe by the Brook- 5m to Waterfall
Outdoor dining

Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views
North River
9.8 out of 10, Exceptional, (81 reviews)
"Nice cozy cabin, close to the spa house."
United States
Anonymous traveller
The price is HK$1,058
HK$1,574 total
includes taxes & fees
29 Apr - 30 Apr
Camp Lillian Gorgeous New Cabin with Mountain Views
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
North River
9.2 out of 10, Wonderful, (67 reviews)
"Had a great stay. Camp had rustic feel and was off the beaten path. Would stay again."
United States
Marcia M.
The price is HK$1,136
HK$1,783 total
includes taxes & fees
29 Apr - 30 Apr
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
Property grounds

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 HK$1,058
HK$1,574 total
includes taxes & fees
28 Apr - 29 Apr
Gorgeous Mountain Top Cabin with Beautiful Views
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!
Lake George
10.0 out of 10, Exceptional, (23 reviews)
"Stay was great!"
United States
Lieishea
The price is HK$1,516
HK$3,518 total
includes taxes & fees
28 Apr - 29 Apr
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Exterior detail

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
10.0 out of 10, Exceptional, (51 reviews)
"Wonderful cabin, very peaceful. "
United States
Anna
The price is HK$1,058
HK$1,583 total
includes taxes & fees
28 Apr - 29 Apr
Handcrafted mountain cabin with gorgeous views
Dining

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 HK$1,332
HK$3,912 total
includes taxes & fees
28 Apr - 29 Apr
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Interior

Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
9.6 out of 10, Exceptional, (67 reviews)
"Cozy cabin, attentive host, wonderful amenities "
United States
Margaret P.
The price is HK$1,058
HK$1,574 total
includes taxes & fees
29 Apr - 30 Apr
Beautiful cottage on scenic Adirondack hobby farm
Property grounds

Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River
North Creek
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful cabin, clean, great location."
United States
Kyle D.
The price is HK$1,058
HK$1,574 total
includes taxes & fees
28 Apr - 29 Apr
Camp RiverWood on the Hudson River
Pool

PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga

PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga
Stony Creek
10.0 out of 10, Exceptional, (28 reviews)
"Great secluded cabin. "
United States
SUZANNE B.
PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga
Exterior

Beautiful cottage on quiet country road walking distance to charming North Creek

Beautiful cottage on quiet country road walking distance to charming North Creek
North Creek
9.8 out of 10, Exceptional, (51 reviews)
"It was exactly what I needed. Quiet and conveniently located for my plans. "
United States
Ruth A.
The price is HK$1,136
HK$1,687 total
includes taxes & fees
29 Apr - 30 Apr
Beautiful cottage on quiet country road walking distance to charming North Creek
Interior

ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain

ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain
North Creek
10.0 out of 10, Exceptional, (110 reviews)
"Our stay was amazing, we felt very at home, and we can’t wait to come back for another visit. "
United States
Michael G.
The price is HK$1,450
HK$1,818 total
includes taxes & fees
28 Apr - 29 Apr
ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain
Outdoor dining

Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
10.0 out of 10, Exceptional, (72 reviews)
"We enjoyed our stay! Very clean and cozy. Very quiet neighborhood and beautiful views of the mountains!! Host was excellent! Thank you!!"
United States
Laura W.
The price is HK$769
HK$1,523 total
includes taxes & fees
3 May - 4 May
Adirondack Bungalow Getaway
Beach

GLAMP RICHARD ON ADIRONDACK FLOWER FARM

GLAMP RICHARD ON ADIRONDACK FLOWER FARM
North River
9.4 out of 10, Exceptional, (21 reviews)
"Everything about this property was carefully designed and crafted to complement the Adirondack theme. The hosts were incredibly friendly and welcoming. After preparing dinner they started a fire in the pit where everyone congregated and traded stories. Highly recommend this property!"
United States
Arlene D.
The price is HK$932
HK$1,296 total
includes taxes & fees
12 May - 13 May
GLAMP RICHARD ON ADIRONDACK FLOWER FARM
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

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Very clean staff was professional and helpful and breakfast was amazing"
Evangelo 2-night trip
Posted 6 hours ago
Fort William Henry Hotel and Conference Center

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
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  • 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?

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.: This highly rated holiday home rental in Chestertown is located on a lake, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Chestertown?

With 60 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. Hudson River and Loon Lake 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.