Chestertown Vacation Rentals

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Chestertown vacation rentals

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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.
$204 nightly
The price is $227
Apr 8 - Apr 9
Total with taxes and fees
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.
$398 nightly
The price is $442
Apr 8 - Apr 9
Total with taxes and fees
The Lily Pad at Loon Lake near Gore Mountain
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.
$190 nightly
The price is $211
Apr 8 - Apr 9
Total with taxes and fees
Little Black Aframe by the Brook- 5m to Waterfall
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, (98 reviews)
"Perfectly cozy, and just right for me and my tiny dog to get away for a few days!"
United States
Bobby R.
$180 nightly
The price is $200
Apr 8 - Apr 9
Total with taxes and fees
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
Interior

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.
$238 nightly
The price is $264
Apr 8 - Apr 9
Total with taxes and fees
Little Red Cabin by the Brook- 5m to Waterfall
Dining

Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls

Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls
Glens Falls
6.4 out of 10, (5 reviews)
"Very large with everything we needed.Fast communication.We enjoyed our stay."
Canada
Mathieu T.
$332 nightly
The price is $369
Apr 8 - Apr 9
Total with taxes and fees
Charming Ground floor 2-bedroom apartment with WiFi, AC in tranquil Glens Falls
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
$189 nightly
The price is $210
Apr 23 - Apr 24
Total with taxes and fees
Trout House Village Resort
Interior

Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
9.6 out of 10, Exceptional, (63 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.
$180 nightly
The price is $200
Apr 8 - Apr 9
Total with taxes and fees
Beautiful cottage on scenic Adirondack hobby farm
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 traveler
$180 nightly
The price is $200
Apr 8 - Apr 9
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, (67 reviews)
"Had a great stay. Camp had rustic feel and was off the beaten path. Would stay again."
United States
Marcia M.
$202 nightly
The price is $224
Apr 8 - Apr 9
Total with taxes and fees
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.
$180 nightly
The price is $200
Apr 8 - Apr 9
Total with taxes and fees
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, (22 reviews)
"Stay was great!"
United States
Lieishea
$405 nightly
The price is $449
Apr 8 - Apr 9
Total with taxes and fees
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
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.
$173 nightly
The price is $192
Apr 16 - Apr 17
Total with taxes and fees
Adirondack Bungalow Getaway
Exterior detail

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
10.0 out of 10, Exceptional, (51 reviews)
"Lovely little cabin tucked away near many hiking trails and the cute town of North Creek. Thanks so much!"
United States
Aileen T.
$180 nightly
The price is $200
Apr 8 - Apr 9
Total with taxes and fees
Handcrafted mountain cabin with gorgeous views
Dining

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
$414 nightly
The price is $447
Apr 8 - Apr 9
Total with taxes and fees
Lakefront-Family & Pet Friendly-Adirondack Cabin
Sports facility

The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.4 out of 10, Very Good, (16 reviews)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
United States
Amanda
$315 nightly
The price is $350
May 3 - May 4
Total with taxes and fees
The Elms Waterfront Cottages
Exterior

Rustic Vacation Rental for Couples near Hoffman Notch, New York

Rustic Vacation Rental for Couples near Hoffman Notch, New York
Schroon Lake
9.0 out of 10, Wonderful, (2 reviews)
"Host was so sweet! Looking forward to staying here again"
United States
Bre Z.
$148 nightly
The price is $169
Apr 9 - Apr 10
Total with taxes and fees
Rustic Vacation Rental for Couples near Hoffman Notch, New York
Exterior

Serene 3-bedroom cabin in North Creek. Close to Gore Mountain ski resort.

Serene 3-bedroom cabin in North Creek. Close to Gore Mountain ski resort.
North Creek
$543 nightly
The price is $603
Apr 10 - Apr 11
Total with taxes and fees
Serene 3-bedroom cabin in North Creek. Close to Gore Mountain ski resort.
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.
$180 nightly
The price is $200
Apr 8 - Apr 9
Total with taxes and fees
Camp RiverWood on the Hudson River
Fireplace

Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin
Indian Lake
$349 nightly
The price is $377
Apr 8 - Apr 9
Total with taxes and fees
Beach - Family & Pet Friendly - Adirondack Cabin
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

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

4/10 Poor
"The front desk staff was great, but the room was lacking in house keeping. The pull out couch had disgusting stains all over it. I had to go to the front desk and ask for sheets and blankets for my daughter to sleep on the pull out couch. There were none in the room. I also had to go to the front desk for toilet paper. Nothing in the bathroom at all. The shower had a huge glob of red hair in the drain. The towels and wash clothes were all stained or dirty. The pool was lacking in supervision. Adults and teenagers jumping from the spa into the pool. Doing flips over top of young children. No clean towels in the pool area, I had to go to the front desk and ask for some. He pushed out a bin full and asked me to take it to the pool area. Other families complemented me for being a life saver. The bathroom located near the pool absolutely disgusting. No paper towels or toilet paper. Feces nothing sprayed all over the toilet and floor. Absolutely disgusting! We took our child back to the room and let her swim around in the Jacuzzi tub we had in our room. Which I had to wipe down with Clorox wipes and rinse prior to her getting into. The tables, ice bin and window sills were dusty. I'm absolutely disappointed and we will not book again. Of all the complaints I made the older man at the front desk was very understanding and tried to fix the problems as soon as possible. Not sure if it's understaffed or just has lazy housekeepers. "
Leeanne 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Lake George

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 $192 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?

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 vacation home rental in Chestertown is located on a lake and has a balcony, a selection of games, and a barbecue grill 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 you can cook with friends or family. 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 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.