Chestertown Vacation Rentals

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Our top choices for Chestertown vacation rentals

Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain
Chestertown
9.8 out of 10, Exceptional, (48 reviews)
"We had a great time at the Lily Pad. Spent a day at Lake Placid and another day at Lake George...plus took in some of the sights and enjoyed the nearby beach and kayaksThe place was very nice...we would stay there again"
United States
Ray V.
Lily Pad South at Loon Lake near Gore Mountain

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
The price is ¥53,140
¥67,362 total
includes taxes & fees
Mar 9 - Mar 10
Authentic Log Cabin with Lake Views and Sauna

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, (40 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is ¥34,117
¥83,244 total
includes taxes & fees
Feb 9 - Feb 10
The Lily Pad at Loon Lake near Gore Mountain

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 ¥39,305
¥84,290 total
includes taxes & fees
Feb 10 - Feb 11
Rustic Adirondack Retreat on Tripp Lake

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (115 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 ¥47,166
¥118,670 total
includes taxes & fees
Mar 8 - Mar 9
Eagles Nest at Loon Lake near Gore Mountain

Safari Tent nestled in the woods on the Schroon River with beach and island!

Safari Tent nestled in the woods on the Schroon River with beach and island!
North Hudson
4.0 out of 10, (4 reviews)
"well, we thought it was going to be glamping. It was worse than camping. It stunk it was dirty. The sheets were never changed. There was dirty dishes. The yard wasn’t mowed. It was just terrible. I would never do this again or recommend anyone to do it."
United States
Glynda
The price is ¥17,923
¥36,420 total
includes taxes & fees
Feb 15 - Feb 16
Safari Tent nestled in the woods on the Schroon River with beach and island!

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (22 reviews)
"Great updated cabin. "
United States
Diane
The price is ¥33,676
¥41,311 total
includes taxes & fees
Feb 9 - Feb 10
Trout House Village Resort

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 ¥16,343
¥33,673 total
includes taxes & fees
Feb 9 - Feb 10
Little Black Aframe by the Brook- 5m to Waterfall

Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin
Indian Lake
The price is ¥25,588
¥55,142 total
includes taxes & fees
Feb 19 - Feb 20
Beach - Family & Pet Friendly - Adirondack Cabin

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Fort Ann
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is ¥34,620
¥64,956 total
includes taxes & fees
Feb 9 - Feb 10
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

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 ¥25,941
¥37,869 total
includes taxes & fees
Feb 9 - Feb 10
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

Rustic Vacation Rental for Couples near Hoffman Notch, New York

Rustic Vacation Rental for Couples near Hoffman Notch, New York
Schroon Lake
The price is ¥19,888
¥26,425 total
includes taxes & fees
Feb 10 - Feb 11
Rustic Vacation Rental for Couples near Hoffman Notch, New York

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
The price is ¥26,727
¥56,542 total
includes taxes & fees
Feb 10 - Feb 11
Lakefront-Family & Pet Friendly-Adirondack Cabin

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
9.8 out of 10, Exceptional, (49 reviews)
"This spot was ideal for us. Beauty, privacy, quiet, comfort. We used it as a base camp for exploring the Adirondacks. Felt remote but nearby North Creek had everything we needed. We had glorious weather and were outside most of the time, but the cabin was big enough for reading and playing games if we had needed to be inside more."
United States
Donna T.
The price is ¥26,727
¥38,916 total
includes taxes & fees
Feb 9 - Feb 10
Handcrafted mountain cabin with gorgeous views

Little Red Cabin by the Brook- 5m to Waterfall

Little Red Cabin by the Brook- 5m to Waterfall
Warrensburg
9.4 out of 10, Exceptional, (19 reviews)
"Would definitely visit again!"
United States
Benjamin M.
The price is ¥18,571
¥41,553 total
includes taxes & fees
Feb 9 - Feb 10
Little Red Cabin by the Brook- 5m to Waterfall

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, (21 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 ¥25,470
¥35,453 total
includes taxes & fees
Feb 11 - Feb 12
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

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 ¥25,941
¥37,869 total
includes taxes & fees
Feb 9 - Feb 10
Gorgeous Mountain Top Cabin with Beautiful Views

Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views
North River
9.8 out of 10, Exceptional, (78 reviews)
"Just what we were looking for. Beautiful and peaceful. "
United States
Lisa S.
The price is ¥25,941
¥37,869 total
includes taxes & fees
Feb 9 - Feb 10
Camp Lillian Gorgeous New Cabin with Mountain Views

Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River
North Creek
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful cabin, clean, great location."
United States
Kyle D.
The price is ¥27,514
¥39,964 total
includes taxes & fees
Feb 9 - Feb 10
Camp RiverWood on the Hudson River

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
Hadley
The price is ¥26,177
¥37,098 total
includes taxes & fees
Feb 9 - Feb 10
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
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

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:

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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?

Elizabeth. A Guest House Near Lake George. : This highly rated vacation home rental in Chestertown is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 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. Our travelers also rate Eagles Nest at Loon Lake near Gore Mountain as a favorite home for rent in Chestertown.

How many vacation rentals will I find in Chestertown?

With 58 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.