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, (49 reviews)
"Very nice place and clean Host was great with emailing Looking forward to go again!"
United States
louis
$213 nightly
The price is $236
Jun 8 - Jun 9
Total with taxes and fees
Lily Pad South at Loon Lake near Gore Mountain

Lily Pad North at Loon Lake near Gore Mountain

Lily Pad North at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (30 reviews)
"Great getaway with a very homely touch, thank you Cheri"
United States
T
Lily Pad North 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, (41 reviews)
"The house is very clean and there was no shortage of fresh towels. "
United States
Sophia H.
$414 nightly
The price is $460
Jun 9 - Jun 10
Total with taxes and fees
The Lily Pad 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, (118 reviews)
"Great house. Great location"
United States
David S.
$632 nightly
The price is $702
Jun 10 - Jun 11
Total with taxes and fees
Eagles Nest at Loon Lake near Gore Mountain

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
9.4 out of 10, Exceptional, (3 reviews)
"Very nice cabin with amenities. Thank you for a great stay."
United States
Joe F.
$380 nightly
The price is $422
Jul 5 - Jul 6
Total with taxes and fees
Authentic Log Cabin with Lake Views and Sauna

Tent in Indian Lake+Pet Friendly+Lake Front

Tent in Indian Lake+Pet Friendly+Lake Front
Indian Lake
$100 nightly
The price is $108
Jun 12 - Jun 13
Total with taxes and fees
Tent in Indian Lake+Pet Friendly+Lake Front

Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.
Hadley
10.0 out of 10, Exceptional, (7 reviews)
"We loved this beautiful peaceful get away!"
United States
Kerrie F.
$195 nightly
The price is $214
Jun 8 - Jun 9
Total with taxes and fees
Lakefront Cabin & Campsite in the Adirondacks - Lake George/Saratoga vicinity.

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (23 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
$189 nightly
The price is $210
Jun 5 - Jun 6
Total with taxes and fees
Trout House Village Resort

Boat, Fish, Hike! Schroon Lake Getaway

Boat, Fish, Hike! Schroon Lake Getaway
3.0 star property
Schroon Lake
$113 nightly
The price is $127
Jun 7 - Jun 8
Total with taxes and fees
Boat, Fish, Hike! Schroon Lake Getaway

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.
$212 nightly
The price is $235
Jun 5 - Jun 6
Total with taxes and fees
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

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)
"This cabin was so cute and comfortable! It had everything we needed plus a view! Can’t wait to stay again "
United States
Amanda B.
$217 nightly
The price is $241
Jun 5 - Jun 6
Total with taxes and fees
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

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, (24 reviews)
"The host was responsive and the cabin is beautiful. Stay was amazing."
United States
Dylan O.
$205 nightly
The price is $226
Jun 8 - Jun 9
Total with taxes and fees
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

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.
$348 nightly
The price is $386
Jun 6 - Jun 7
Total with taxes and fees
PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga

Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
North Creek
9.4 out of 10, Exceptional, (15 reviews)
"The host was very responsive and helpful. The space was very cozy and had all the basics. Location was perfect for a ski weekend."
United States
annie k.
$209 nightly
The price is $228
Jun 8 - Jun 9
Total with taxes and fees
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

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, (54 reviews)
"It was a nice place, comfortable, nice location. Could have been cleaner but we had a nice relaxing time. "
United States
Mary M.
$223 nightly
The price is $248
Jun 14 - Jun 15
Total with taxes and fees
Beautiful cottage on quiet country road walking distance to charming North Creek

GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND VIEWS

GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND VIEWS
North River
9.0 out of 10, Wonderful, (26 reviews)
"Beautiful property...very unique "
United States
Ari
$129 nightly
The price is $143
Jun 5 - Jun 6
Total with taxes and fees
GLAMP SUZANNE: CANVAS CABIN ON PRETTY ADIRONDACK FARM OFFERS PRIVACY AND 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, (81 reviews)
"Beautiful place and the cabin was perfect for local skiing and hiking."
United States
Ken B.
$217 nightly
The price is $241
Jun 8 - Jun 9
Total with taxes and fees
Camp Lillian Gorgeous New Cabin with Mountain Views

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
$199 nightly
The price is $221
Jun 5 - Jun 6
Total with taxes and fees
Handcrafted mountain cabin with gorgeous views

< 1 Mi to Boat Launch! Schroon Lake Basecamp

< 1 Mi to Boat Launch! Schroon Lake Basecamp
3.0 star property
Schroon Lake
$126 nightly
The price is $142
Jun 5 - Jun 6
Total with taxes and fees
< 1 Mi to Boat Launch! Schroon Lake Basecamp

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.
$190 nightly
The price is $211
Jun 5 - Jun 6
Total with taxes and fees
Beautiful cottage on scenic Adirondack hobby 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

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 $115 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?

Adirondack Bungalow Getaway: Located near Chestertown, this vacation home rental is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals will I find in Chestertown?

With 61 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. Hudson River and Loon Lake 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.