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

Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Chestertown holiday rentals

Smart TV

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 HK$2,118
HK$2,690 total
includes taxes & fees
3 Aug - 4 Aug
Authentic Log Cabin with Lake Views and Sauna
Outdoor dining

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.
Adirondack Mountains Cottage Near Gore Mountain!
Games room

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 HK$823
HK$2,014 total
includes taxes & fees
28 Jul - 29 Jul
The Office at North Creek All Season Rental
Interior

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 HK$1,082
HK$1,331 total
includes taxes & fees
28 Jul - 29 Jul
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Exterior

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 HK$1,059
HK$2,127 total
includes taxes & fees
28 Jul - 29 Jul
Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied
Exterior

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 HK$776
HK$1,945 total
includes taxes & fees
30 Jul - 31 Jul
Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6
Living area

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 HK$1,906
HK$4,788 total
includes taxes & fees
28 Jul - 29 Jul
2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &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, (11 reviews)
"Great communication from the host, and everything matched the listing perfectly as pictured! "
United States
Jakob M.
The price is HK$1,101
HK$2,049 total
includes taxes & fees
4 Aug - 5 Aug
Little Black Aframe by the Brook- 5m to Waterfall
Property grounds

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 HK$1,412
HK$2,020 total
includes taxes & fees
30 Jul - 31 Jul
Camp RiverWood on the Hudson River
Exterior detail

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 HK$800
HK$1,971 total
includes taxes & fees
28 Jul - 29 Jul
Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6
Exterior

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, (55 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
The price is HK$1,490
HK$2,142 total
includes taxes & fees
30 Jul - 31 Jul
Beautiful cottage on quiet country road walking distance to charming North Creek
Outdoor dining

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 HK$878
HK$2,067 total
includes taxes & fees
28 Jul - 29 Jul
Gore Mountain Lift View: North Creek Main St Apt 2
Interior

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 HK$1,137
HK$1,567 total
includes taxes & fees
28 Jul - 29 Jul
Glamp Thomas On Adk Farm Offers Privacy, Stargazing And Mountain Views
Interior

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 HK$1,082
HK$1,331 total
includes taxes & fees
28 Jul - 29 Jul
Schroon Lake Room < 1 Mi to Marina & Beach!
Beach

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 HK$1,137
HK$1,550 total
includes taxes & fees
28 Jul - 29 Jul
GLAMP RICHARD ON ADIRONDACK FLOWER FARM
Exterior

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
9.4 out of 10, Exceptional, (21 reviews)
"Had a very nice stay, close to Gore"
United States
Terence M.
The price is HK$776
HK$1,945 total
includes taxes & fees
28 Jul - 29 Jul
Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8
Property grounds

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 HK$1,680
HK$2,909 total
includes taxes & fees
28 Jul - 29 Jul
Lovely 3-bedroom house close to Gore Mountain for skiing.
Outdoor dining

Adirondack Bungalow Getaway

Adirondack Bungalow Getaway
Warrensburg
9.8 out of 10, Exceptional, (81 reviews)
"Adirondack Bungalow was a very nice place and I would stay again. We are just sorry we didn't have more time to explore the area. Communication with the host was easy and the place was clean and had everything you would have needed to make your stay comfortable."
United States
Gary A.
Adirondack Bungalow Getaway
WiFi

Lake George Escape - Campground

Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very good, (181 reviews)
"Place and space"
United States
Laser Brookes
The price is HK$2,327
HK$2,582 total
includes taxes & fees
24 Aug - 25 Aug
Lake George Escape - Campground
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, (21 reviews)
"Would definitely visit again!"
United States
Benjamin M.
The price is HK$1,059
HK$2,237 total
includes taxes & fees
28 Jul - 29 Jul
Little Red Cabin by the Brook- 5m to Waterfall
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

Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

8/10 Good
"We didn't appreciate when we asked for towels that they were left outside our room door in a garbage bag. No housekeeping"
Andreas 3-night trip
Posted less than an hour ago
Six Flags Great Escape Lodge & Indoor Waterpark

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:

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

Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Eagles Nest at Loon Lake near Gore Mountain: This highly rated holiday home rental in Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Chestertown?

With 60 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.