Photo by Julie Miller

Search the Best Cabins in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chestertown cabin rentals

Exterior
Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
$629 nightly
The price is $698
Dec 23 - Dec 24
Total with taxes and fees
Authentic Log Cabin with Lake Views and Sauna
Luxury Cabin | Egyptian cotton sheets, premium bedding, individually decorated
Trout House Village Resort

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (19)
"Great updated cabin. "
United States
Diane
$189 nightly
The price is $210
Dec 23 - Dec 24
Total with taxes and fees
Trout House Village Resort
Exterior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
North River
10.0 out of 10, Exceptional, (94)
"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.
$216 nightly
The price is $240
Dec 23 - Dec 24
Total with taxes and fees
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Exterior
Little Black Aframe by the Brook- 5m to Waterfall

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)
"My wife and I had a great time. We would stay here again. Great communication with the host. Thanks!"
United States
Ted D.
$198 nightly
The price is $219
Dec 23 - Dec 24
Total with taxes and fees
Little Black Aframe by the Brook- 5m to Waterfall
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

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Hadley
10.0 out of 10, Exceptional, (21)
"Perfect remote location for a weekend away! Jackie is a great host and cabin was very clean and delicate. "
United States
Hanna D.
$206 nightly
The price is $222
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Exterior
Little Red Cabin by the Brook- 5m to Waterfall

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)
"Beautiful property, we enjoyed the quiet very much. "
United States
Susan T.
$238 nightly
The price is $264
Jan 4 - Jan 5, 2026
Total with taxes and fees
Little Red Cabin by the Brook- 5m to Waterfall
Exterior
Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm

Beautiful cottage on scenic Adirondack hobby farm
North River
9.6 out of 10, Exceptional, (60)
"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.
$199 nightly
The price is $221
Dec 23 - Dec 24
Total with taxes and fees
Beautiful cottage on scenic Adirondack hobby farm
Exterior
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR
North River
9.2 out of 10, Wonderful, (63)
"See you next year amazing stay great food loved the bird camp cabin—- Brian, Darlene, Gracie and Hayden "
United States
Brian W.
$239 nightly
The price is $265
Dec 23 - Dec 24
Total with taxes and fees
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR
Exterior
Camp Lillian Gorgeous New Cabin with Mountain 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, (77)
"Just what we were looking for. Beautiful and peaceful. "
United States
Lisa S.
$217 nightly
The price is $241
Jan 4 - Jan 5, 2026
Total with taxes and fees
Camp Lillian Gorgeous New Cabin with Mountain Views
Exterior detail
Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views

Handcrafted mountain cabin with gorgeous views
North River
9.8 out of 10, Exceptional, (49)
"Lovely little cabin tucked away near many hiking trails and the cute town of North Creek. Thanks so much!"
United States
Aileen T.
$222 nightly
The price is $246
Dec 24 - Dec 25
Total with taxes and fees
Handcrafted mountain cabin with gorgeous views
Exterior
Gorgeous mountain views and private!

Gorgeous mountain views and private!

Gorgeous mountain views and private!
North River
10.0 out of 10, Exceptional, (35)
"We enjoyed our stay very much. A little slice of heaven. "
United States
Kelly
$216 nightly
The price is $240
Dec 23 - Dec 24
Total with taxes and fees
Gorgeous mountain views and private!
Exterior
Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River
North Creek
9.8 out of 10, Exceptional, (6)
"Beautiful cabin, clean, great location."
United States
Kyle D.
$229 nightly
The price is $254
Dec 23 - Dec 24
Total with taxes and fees
Camp RiverWood on the Hudson River
Exterior
Riverbend Cabin - Wonderful 2-bedroom home

Riverbend Cabin - Wonderful 2-bedroom home

Riverbend Cabin - Wonderful 2-bedroom home
2.0 star property
Hadley
$285 nightly
The price is $308
Dec 23 - Dec 24
Total with taxes and fees
Riverbend Cabin - Wonderful 2-bedroom home
Exterior
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!

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Lake George
10.0 out of 10, Exceptional, (16)
"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.
$374 nightly
The price is $415
Jan 4 - Jan 5, 2026
Total with taxes and fees
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Interior
Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin

Beach - Family & Pet Friendly - Adirondack Cabin
Indian Lake
10.0 out of 10, Exceptional, (1)
$352 nightly
The price is $380
Jan 8 - Jan 9, 2026
Total with taxes and fees
Beach - Family & Pet Friendly - Adirondack Cabin
Exterior
Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
10.0 out of 10, Exceptional, (2)
"Simple mountain cabin in remote location. Space in great for a couple or two singles. Property has plenty of elbow room with several other structures spread out across a giant clearing next to a lake. We hiked, swam, kayaked, fished and relaxed and enjoyed the views. We cooked dinner on the charcoal grill, and drank our morning coffee while listening to the birds. Hosts were attentive and chatted with us a few times. "
United States
Kerstin Y.
$328 nightly
The price is $354
Jan 8 - Jan 9, 2026
Total with taxes and fees
Lakefront-Family & Pet Friendly-Adirondack Cabin
Exterior
Luxury Cabin Sleeps 4 to 7 - mins to Lake George

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, (7)
"Cabin was great! It was nice and secluded, but at the same time clean and modern. Plenty of place for the kids to spread out and also enjoy family dinners together. Hot tub and firepit were a nice touch."
United States
Joel B.
$474 nightly
The price is $518
Jan 11 - Jan 12, 2026
Total with taxes and fees
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Exterior
Superb Nature Lodge 5mns to Gore Mountain w/Large Hot Tub, Firepit & Fireplace!

Superb Nature Lodge 5mns to Gore Mountain w/Large Hot Tub, Firepit & Fireplace!

Superb Nature Lodge 5mns to Gore Mountain w/Large Hot Tub, Firepit & Fireplace!
Chester
10.0 out of 10, Exceptional, (10)
"Great house for a ski weekend at Gore mountain. Very close to the slopes, and the house is beautiful. "
United States
Samir R.
$625 nightly
The price is $666
Jan 2 - Jan 3, 2026
Total with taxes and fees
Superb Nature Lodge 5mns to Gore Mountain w/Large Hot Tub, Firepit & Fireplace!
Exterior
Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
$333 nightly
The price is $360
Dec 23 - Dec 24
Total with taxes and fees
Lakefront-Family & Pet Friendly-Adirondack Cabin
Exterior
Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
10.0 out of 10, Exceptional, (1)
"Perfect getaway for the Adirondacks- would 100% recommend and stay here again. Excellent cabin with plenty of room for everyone to stay and relax."
United States
Lainie H.
$488 nightly
The price is $527
Jan 8 - Jan 9, 2026
Total with taxes and fees
Lakefront-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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"An overall very pleasant stay. From the front desk staff member who helped check me in, to every other employee I interacted with throughout my short stay. Compliments to the chef for one of the best Huevos Rancharos I’ve had. "
Kyle 1-night trip
Posted 3 days ago
The Queensbury Hotel

Find out more about Chestertown

Chestertown Cabin Rentals information

Number of reviews
471
Accommodation
173 Cabin Rentals
Lowest Price
$210
Highest Price
$698

Frequently asked questions

What are the best cabins near Chestertown?
Stay in the great outdoors without sacrificing the comforts at one of our 588 cabins in and around Chestertown. Whether you have relaxation or adventure on your mind, Cabin - Romantic Retreat: Mt. Views, Hot Tub offers plenty of both. Alternatively, book Relaxing Log Cabin Retreat Minutes From Whiteface and kick back among picturesque surroundings.
Are there cheap cabins in Chestertown?
For a nicely priced vacation in nature, look no further than our cheap cabins in Chestertown. Wake in the morning to the sound of birds chirping from one of our cozy cabins priced from $210 to $698 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best luxury cabins near Chestertown?
After spending your day adventuring in Mother Nature, return home to the comfort and style of a Chestertown luxury cabin. Robert Frost Mountain Cabins is a perfect option if you'd love to pamper yourself. You'll enjoy the plush touches here, such as pillow top mattresses and massage services. Killington Mountain Home Hottub And 5 Min To Skiing 3 Bedroom Home By Redawning is another impressive stay. Make the most of a spa tub, fitness classes and a whole lot more.
What are the best river cabins near Chestertown?
If you're seeking a homely abode steps from the water, a Chestertown river cabin is hard to go past. Head for Log Cabin On The Hudson and let any worries on your mind vanish downstream. Useful amenities here include snowsport activities and outdoor furniture. Another leading riverside rental is Cozy Cabin Near A Creek In The Forest. Its conveniences include snowsport activities, a nearby marina and more.
What are the best cabins with pools near Chestertown?
Slip on your swimwear and go for a few laps whenever you want when you stay at one of our cabin rentals with a pool. Canvas Cabin On Pretty Farm is a top choice. A porch and a patio are some other amenities that'll help make your stay comfortable. Alternatively, spend your escape at The Gold Eagle Cottage 15. As well as a refreshing pool, this cabin offers a porch and a swimming pool.
Can I find beach cabins near Chestertown?
Enjoy your fix of sun and sea air at Cozy Private Lake Cabin Minutes To Lake George And Saratoga Springs. One of our finest Chestertown beach cabins, it has on-site watersports and beach sun loungers. You can also spend carefree days along the shoreline at Log Cabin On The Hudson. Clothes washing facilities and children's activities will make your visit even more pleasurable.
What are the best weekend cabin rentals in Chestertown?
If you'd like to spend a handful of carefree days immersed in nature, Cabin - High Peaks Mountain Retreat is the perfect place. Head here for a long weekend and make use of amenities including on-site watersports and a porch. Another excellent choice is Private Lake - Front Cabin With Walk. Offering a patio, a firepit and plenty of peace and quiet, you'll go home feeling like a new person.
What are the best cabin prices in Chestertown?
If you want to save a few bucks on your stay, we've got some incredible offers on Chestertown cabins that won't hurt your hip pocket. How does $210 a night sound to you?
Can I find log cabins in Chestertown?
Start your day with a hot cup of coffee in your comfy log cabin and then spend the rest of your time snow shoeing and canoeing. Sound like your perfect vacation? Head for Log Cabin On The Hudson. Another wooden getaway with plenty of charm and comforts is Authentic Log Cabin - Mountain Views. Nearby activities like snowmobiling and canoeing will add to your experience here.
What are the highest-rated cabins in Chestertown?
There are some properties that tick just about every box. Ultimate Couples Getaway Quiet And Private Lakeside Cottage In The Adirondacks is a prime example. With an impressive rating, it comes with useful amenities like on-site watersports, a patio and much more. Another fantastic option is Athol Cabin With Deck And Fire Pit. A patio and a firepit are just a couple of the conveniences waiting for you here.
What are the top things to see and do in Chestertown?
Any unforgettable cabin stay just has to involve checking out some sights. For example, Loon Lake Beach. It's considered one of the most popular attractions in Chestertown. If you'd like to travel a little farther out, rent a set of wheels and make your way to Loon Lake.
Why should I book a cabin in Chestertown?
Comfort, affordability, rustic charm — there are countless great reasons to choose a Chestertown cabin. Leave behind the noise of the concrete jungle and wake up to the sweet sound of birdsong. There's so much adventure just beyond your door too. Whether you're on vacation with friends, relatives or your other half, you'll locate the perfect cabin on Expedia.
What are the top nature cabins in Chestertown?
The outdoors won't be the only thing you'll be experiencing lots of at a nature cabin in Chestertown. Adventure is everywhere you look too. Hide away at Log Cabin On The Hudson and make time for some nearby golfing and nearby cross-country skiing. Another standout is Cozy Cabin Near A Creek In The Forest. It's well known for its home comforts as well as its mountain climbing and nearby motor boating opportunities nearby.
What are some of the best cabins near Lake George Dog Beach in Chestertown?
Rustic Log Cabin - Walking Distance To Village is a popular option in Lake George Dog Beach. Plenty of comforts, a postcard-perfect backdrop and activities such as jet skiing and nearby rock climbing make it the ideal escape. Walking Distance To Downtown Lake George Village is another retreat where adventure and nature combine. Settle in here and add water tubing and hiking to your to-do list.

Explore a world of travel with Expedia