A waterfront town with a pier, dock, and several buildings.

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chestertown vacation rentals

Outdoor dining

1. 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, (50 reviews)
"Very nice place and clean Host was great with emailing Looking forward to go again!"
United States
louis
The price is SAR 428
SAR 1,017 total
includes taxes & fees
20 Sep - 21 Sep
Lily Pad South at Loon Lake near Gore Mountain
Outdoor dining

2. 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, (42 reviews)
"The house is very clean and there was no shortage of fresh towels. "
United States
Sophia H.
The price is SAR 751
SAR 1,901 total
includes taxes & fees
20 Sep - 21 Sep
The Lily Pad at Loon Lake near Gore Mountain
Smart TV

3. 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.
The price is SAR 1,014
SAR 1,288 total
includes taxes & fees
25 Aug - 26 Aug
Authentic Log Cabin with Lake Views and Sauna
Exterior

4. Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (122 reviews)
"Great house. Great location"
United States
David S.
The price is SAR 1,126
SAR 2,834 total
includes taxes & fees
13 Sep - 14 Sep
Eagles Nest at Loon Lake near Gore Mountain
Outdoor dining

5. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
9.8 out of 10, Exceptional, (130 reviews)
"Easy to get to yet very serene. Anything you want or need was provided in the cabin. "
United States
Roy M.
The price is SAR 597
SAR 1,530 total
includes taxes & fees
25 Aug - 26 Aug
Adirondack Mountains Cottage Near Gore Mountain!
WiFi (surcharge)

6. Lake George Escape - Campground

Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very Good, (195 reviews)
"Rent the golf carts and explore the whole campsite! Great and fun stay"
United States
Brittany
The price is SAR 616
SAR 684 total
includes taxes & fees
21 Sep - 22 Sep
Lake George Escape - Campground
Apartment (0 Bedroom) | Interior

7. Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
10.0 out of 10, Exceptional, (1 review)
"Clean, comfortable room. Very friendly and welcoming hosts."
United States
Kevin
The price is SAR 518
SAR 637 total
includes taxes & fees
24 Aug - 25 Aug
Schroon Lake Room < 1 Mi to Marina & Beach!
Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, iron/ironing board, WiFi (free)

8. Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.6 out of 10, Exceptional, (25 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is SAR 562
SAR 717 total
includes taxes & fees
8 Sep - 9 Sep
Trout House Village Resort
Exterior detail

9. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6
North Creek
9.6 out of 10, Exceptional, (5 reviews)
"Clean, convenient, and lots of space for the three of us. "
United States
Michael
The price is SAR 364
SAR 919 total
includes taxes & fees
24 Aug - 25 Aug
Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6
Living area

10. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain
Warrensburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was beautiful, lots of natural light. There was a snow storm the day we arrived and they had come and plowed the large drive the next night so we didnt need to shovel much. Everything was very clean and the host was very helpful and responsive! Would definitely stay again!"
United States
Teresa B.
The price is SAR 912
SAR 2,309 total
includes taxes & fees
31 Aug - 1 Sep
2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain
Exterior

11. 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.
The price is SAR 375
SAR 931 total
includes taxes & fees
16 Sep - 17 Sep
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
Property grounds

12. Camp RiverWood on the Hudson River

Camp RiverWood on the Hudson River
North Creek
9.8 out of 10, Exceptional, (11 reviews)
"Great cabin! Great location!"
United States
Paul N.
The price is SAR 676
SAR 979 total
includes taxes & fees
24 Aug - 25 Aug
Camp RiverWood on the Hudson River
Outdoor dining

13. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (84 reviews)
"Enjoyed our weekend stay here. Close to the main road and a short drive to Lake George. House was very clean and met all our needs. Will definitely stay here again if we visit the area."
United States
Virginia (Ginger) S.
The price is SAR 409
SAR 771 total
includes taxes & fees
13 Sep - 14 Sep
Adirondack Bungalow Getaway
Exterior

14. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
North Creek
9.0 out of 10, Wonderful, (24 reviews)
"Proximity to downtown and nearby attractions."
United States
joseph
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
TV

15. Lovely 3-bedroom house close to Gore Mountain for skiing.

Lovely 3-bedroom house close to Gore Mountain for skiing.
North Creek
9.4 out of 10, Exceptional, (3 reviews)
"Very cute and cozy / responsive and helpful host"
United States
Renee B.
The price is SAR 702
SAR 1,246 total
includes taxes & fees
21 Sep - 22 Sep
Lovely 3-bedroom house close to Gore Mountain for skiing.
Interior

16. Glamp Thomas On Adk Farm Offers Privacy, Stargazing And Mountain Views

Glamp Thomas On Adk Farm Offers Privacy, Stargazing And Mountain Views
North River
9.8 out of 10, Exceptional, (29 reviews)
"Perfect location "
United States
Laura F.
The price is SAR 488
SAR 679 total
includes taxes & fees
25 Aug - 26 Aug
Glamp Thomas On Adk Farm Offers Privacy, Stargazing And Mountain Views
Apartment (0 Bedroom) | Interior

17. Walk to Schroon Lake! Studio w/ Shared Fire Pit

Walk to Schroon Lake! Studio w/ Shared Fire Pit
3.0 star property
Schroon Lake
The price is SAR 518
SAR 637 total
includes taxes & fees
24 Aug - 25 Aug
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Game room

18. The Office at North Creek All Season Rental

The Office at North Creek All Season Rental
North Creek
8.8 out of 10, Excellent, (13 reviews)
"Fun property to stay at! We enjoyed our stay and hope to come back during ski season. "
United States
Brandon A.
The price is SAR 436
SAR 1,014 total
includes taxes & fees
24 Aug - 25 Aug
The Office at North Creek All Season Rental
Terrace/patio

19. 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, (11 reviews)
"Great communication from the host, and everything matched the listing perfectly as pictured! "
United States
Jakob M.
The price is SAR 401
SAR 817 total
includes taxes & fees
24 Aug - 25 Aug
Little Black Aframe by the Brook- 5m to Waterfall
Exterior

20. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Minerva
10.0 out of 10, Exceptional, (1 review)
"Absolutely fantastic! Hosts were very kind and responsive. Property was clean and cozy. "
United States
Christine T.
The price is SAR 507
SAR 1,018 total
includes taxes & fees
24 Aug - 25 Aug
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
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

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

10/10 Excellent
"Really clean. Very quaint. Lovely owners. Close to “town” and close to lake. Perfect for our purposes."
Meghan 2-night trip
Posted 2 hours ago
Pine Tree Motel & Cabins

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. Our travelers also rate Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool. as a favorite home for rent in Chestertown.

How many vacation rentals will I find in Chestertown?

With 60 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?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach 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.