Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Chestertown vacation rentals

Exterior

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.
$654 nightly
The price is $726
Feb 23 - Feb 24
Total with taxes and fees
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
Chestertown
$339 nightly
The price is $376
Mar 3 - Mar 4
Total with taxes and fees
Authentic Log Cabin with Lake Views and Sauna
Interior

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.
Rustic Adirondack Retreat on Tripp Lake
Cabin, 1 Bedroom, Non Smoking, Lake View | 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)
"Great updated cabin. "
United States
Diane
$237 nightly
The price is $263
Feb 22 - Feb 23
Total with taxes and fees
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, (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.
$217 nightly
The price is $241
Feb 22 - Feb 23
Total with taxes and fees
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
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, (79 reviews)
"Nice cozy cabin, close to the spa house."
United States
Anonymous traveler
$217 nightly
The price is $241
Feb 24 - Feb 25
Total with taxes and fees
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, (66 reviews)
"See you next year amazing stay great food loved the bird camp cabin—- Brian, Darlene, Gracie and Hayden "
United States
Brian W.
$240 nightly
The price is $266
Feb 22 - Feb 23
Total with taxes and fees
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN 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, (19 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.
$405 nightly
The price is $449
Feb 22 - Feb 23
Total with taxes and fees
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Property grounds

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.
$342 nightly
The price is $379
Feb 22 - Feb 23
Total with taxes and fees
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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.
$204 nightly
The price is $224
Feb 24 - Feb 25
Total with taxes and fees
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Terrace/patio

Lake George Water Front Cabin Spectacular Views

Lake George Water Front Cabin Spectacular Views
Ticonderoga
9.6 out of 10, Exceptional, (35 reviews)
"Incredible stay! The perfect spot "
United States
Ian S.
$1,017 nightly
The price is $1,129
Feb 22 - Feb 23
Total with taxes and fees
Lake George Water Front Cabin Spectacular Views
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, (50 reviews)
"It was exactly what I needed. Quiet and conveniently located for my plans. "
United States
Ruth A.
$246 nightly
The price is $273
Feb 22 - Feb 23
Total with taxes and fees
Beautiful cottage on quiet country road walking distance to charming North Creek
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, (42 reviews)
"The place was as charming as the pictures, and the views were incredible. We would also recommend the bath/hot tub as well, it was a relaxing and lovely stay!"
United States
Jennifer A.
$242 nightly
The price is $269
Feb 22 - Feb 23
Total with taxes and fees
Sweet New Cabin With Amazing Views Of The Hudson River
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.
$629 nightly
The price is $698
Feb 22 - Feb 23
Total with taxes and fees
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
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.
$480 nightly
The price is $524
Feb 22 - Feb 23
Total with taxes and fees
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Property grounds

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.
$229 nightly
The price is $254
Feb 23 - Feb 24
Total with taxes and fees
Camp RiverWood on the Hudson River
Exterior detail

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.
$223 nightly
The price is $248
Feb 24 - Feb 25
Total with taxes and fees
Handcrafted mountain cabin with gorgeous views
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
$739 nightly
The price is $835
Mar 2 - Mar 3
Total with taxes and fees
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Interior

Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls

Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
Glens Falls
10.0 out of 10, Exceptional, (7 reviews)
"Everything was exactly as advertised, wonderful stay!"
United States
Jim W.
$828 nightly
The price is $919
Feb 22 - Feb 23
Total with taxes and fees
Spectacular Roof Top Patio 3bd Apartment in Downtown Glens Falls
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
"Kind people"
Drew 1-night trip
Posted 2 days ago
Six Flags Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Everything you need to know about Chestertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $194 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 59 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.