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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chestertown vacation rentals

Smart TV

1. 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 ￥43,035
￥54,669 total
includes taxes & fees
Aug 18 - Aug 19
Authentic Log Cabin with Lake Views and Sauna
Outdoor dining

2. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
9.8 out of 10, Exceptional, (129 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 ￥25,343
￥64,931 total
includes taxes & fees
Aug 25 - Aug 26
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

3. 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 ￥18,011
￥42,361 total
includes taxes & fees
Aug 17 - Aug 18
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
Exterior detail

4. 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 ￥18,170
￥42,538 total
includes taxes & fees
Aug 19 - Aug 20
Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6
Terrace/patio

5. 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 ￥18,936
￥37,295 total
includes taxes & fees
Aug 31 - Sep 1
Little Black Aframe by the Brook- 5m to Waterfall
Game room

6. 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 ￥19,446
￥44,301 total
includes taxes & fees
Aug 17 - Aug 18
The Office at North Creek All Season Rental
Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, iron/ironing board, WiFi (free)

7. 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 ￥21,197
￥27,513 total
includes taxes & fees
Sep 8 - Sep 9
Trout House Village Resort
Property grounds

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

Walk to Schroon Lake! Studio w/ Shared Fire Pit
Schroon Lake
10.0 out of 10, Exceptional, (1 review)
"Our room was very comfortable. Had everything that we needed. Julie was very friendly and greeted us as we arrived. It was very clean, quiet and close to the village of Schroon Lake. It was a busy weekend for the area. We got take out at DeCeseare's Pizza. Took it back to the room and relaxed.There were plenty of toiletries and soft towels in the bathroom. Definitely would stay there again."
United States
Kim
The price is ￥15,768
￥27,896 total
includes taxes & fees
Aug 19 - Aug 20
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Apartment (0 Bedroom) | Interior

9. 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 ￥21,979
￥27,037 total
includes taxes & fees
Aug 26 - Aug 27
Schroon Lake Room < 1 Mi to Marina & Beach!
Property grounds

10. 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 ￥28,669
￥41,546 total
includes taxes & fees
Aug 26 - Aug 27
Camp RiverWood on the Hudson River
Outdoor dining

11. Gore Mountain Lift View: North Creek Main St Apt 2

Gore Mountain Lift View: North Creek Main St Apt 2
North Creek
9.0 out of 10, Wonderful, (10 reviews)
"Great location… Enjoyed our stay"
United States
Lynda N.
The price is ￥22,139
￥47,280 total
includes taxes & fees
Aug 18 - Aug 19
Gore Mountain Lift View: North Creek Main St Apt 2
Exterior

12. 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 ￥21,501
￥43,014 total
includes taxes & fees
Aug 14 - Aug 15
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
TV

13. 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 ￥29,941
￥53,580 total
includes taxes & fees
Sep 12 - Sep 13
Lovely 3-bedroom house close to Gore Mountain for skiing.
Living area

14. 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 ￥40,405
￥100,185 total
includes taxes & fees
Aug 19 - Aug 20
2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain
Interior

15. GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM

GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
North River
9.8 out of 10, Exceptional, (42 reviews)
"We had such a wonderful time! The location is so peaceful and scenic and the drive to 13th lake for swimming was just a few minutes. Absolutely hope to stay again!"
United States
Gretta G.
The price is ￥20,705
￥28,286 total
includes taxes & fees
Sep 1 - Sep 2
GLAMP BERNICE ON BEAUTIFUL ADIRONDACK HOBBY FARM
Exterior

16. 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, (22 reviews)
"Had a very nice stay, close to Gore"
United States
Terence M.
The price is ￥19,112
￥43,036 total
includes taxes & fees
Sep 9 - Sep 10
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
Beach

17. GLAMP RICHARD ON ADIRONDACK FLOWER FARM

GLAMP RICHARD ON ADIRONDACK FLOWER FARM
North River
9.4 out of 10, Exceptional, (22 reviews)
"Peaceful weekend with family. "
United States
Timothy
The price is ￥20,705
￥28,286 total
includes taxes & fees
Sep 1 - Sep 2
GLAMP RICHARD ON ADIRONDACK FLOWER FARM
Interior

18. 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, (21 reviews)
"Would definitely visit again!"
United States
Benjamin M.
The price is ￥21,501
￥45,435 total
includes taxes & fees
Aug 31 - Sep 1
Little Red Cabin by the Brook- 5m to Waterfall
Apartment (0 Bedroom) | Interior

19. Cozy Room Near Schroon Lake Marina, Town & Beach!

Cozy Room Near Schroon Lake Marina, Town & Beach!
3.0 star property
Schroon Lake
6.0 out of 10, (2 reviews)
"Help!! We didn’t stay at this property due to the property stating it was lakefront and marina. The property was in complete disrepair condition. Junk cars, high weeds, room smelled of smoke. I would request a refund."
United States
Pamela
The price is ￥21,979
￥27,037 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Room Near Schroon Lake Marina, Town & Beach!
Terrace/patio

20. 7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
Johnsburg
10.0 out of 10, Exceptional, (4 reviews)
"Nice place and area, nice and quiet"
United States
thomas c.
The price is ￥22,218
￥64,617 total
includes taxes & fees
Aug 17 - Aug 18
7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10
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

Depe Dene Lakeside Resort

Depe Dene Lakeside Resort

10/10 Excellent
"Overall great stay"
Rob 1-night trip
Posted 7 hours ago
Depe Dene Lakeside Resort

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
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  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

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 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?

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.