Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

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)
"House is great… improvements are in the works and look to be amazing! "
United States
Serena
The price is HK$2,819
HK$3,581 total
includes taxes & fees
25 May - 26 May
Authentic Log Cabin with Lake Views and Sauna
2 bedrooms, desk, iron/ironing board, travel cot

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
The price is HK$861
HK$2,086 total
includes taxes & fees
1 Jun - 2 Jun
Lily Pad South at Loon Lake near Gore Mountain
Exterior

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.
The price is HK$2,083
HK$5,624 total
includes taxes & fees
26 May - 27 May
Eagles Nest at Loon Lake near Gore Mountain
Outdoor dining

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
The price is HK$767
HK$1,973 total
includes taxes & fees
25 May - 26 May
Lily Pad North at Loon Lake near Gore Mountain
Outdoor dining

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.
The price is HK$1,308
HK$3,651 total
includes taxes & fees
20 May - 21 May
The Lily Pad at Loon Lake near Gore Mountain
WiFi

Lake George Escape - Campground

Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very good, (169 reviews)
"Nice place to staying "
United States
RAFAL
The price is HK$955
HK$1,060 total
includes taxes & fees
20 May - 21 May
Lake George Escape - Campground
Egyptian cotton sheets, premium bedding, individually decorated

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (22 reviews)
"spotless room w an incredible view!"
United States
Joanne
The price is HK$1,172
HK$1,496 total
includes taxes & fees
5 Jun - 6 Jun
Trout House Village Resort
Sports facility

The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.4 out of 10, Very good, (16 reviews)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
United States
Amanda
The price is HK$2,467
HK$2,738 total
includes taxes & fees
20 May - 21 May
The Elms Waterfront Cottages
Exterior

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
The price is HK$1,752
HK$6,270 total
includes taxes & fees
7 Jun - 8 Jun
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Terrace/patio

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, (23 reviews)
"Stay was great!"
United States
Lieishea
The price is HK$2,290
HK$4,646 total
includes taxes & fees
20 May - 21 May
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Pool

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.
The price is HK$1,403
HK$3,026 total
includes taxes & fees
22 May - 23 May
PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga
Exterior

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)
"Perfectly cozy, and just right for me and my tiny dog to get away for a few days!"
United States
Bobby R.
The price is HK$1,292
HK$1,825 total
includes taxes & fees
18 Jun - 19 Jun
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
Living area

Beach Cottages at Lake George

Beach Cottages at Lake George
3.0 star property
Lake George
9.0 out of 10, Wonderful, (7 reviews)
"We were amazed how cute and comfortable the cabin was definitely staying here again."
United States
Jessie
The price is HK$1,552
HK$1,723 total
includes taxes & fees
2 Jun - 3 Jun
Beach Cottages at Lake George
Dining

Lakefront-Family & Pet Friendly-Adirondack Cabin

Lakefront-Family & Pet Friendly-Adirondack Cabin
Indian Lake
The price is HK$2,006
HK$3,638 total
includes taxes & fees
20 May - 21 May
Lakefront-Family & Pet Friendly-Adirondack Cabin
Exterior

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Fort Ann
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is HK$2,647
HK$4,346 total
includes taxes & fees
17 Jun - 18 Jun
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Interior

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.
The price is HK$1,370
HK$2,086 total
includes taxes & fees
25 May - 26 May
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
Smart TV

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, (8 reviews)
"Awesome visit, everything as described!"
United States
Adam H.
The price is HK$1,253
HK$3,815 total
includes taxes & fees
21 May - 22 May
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Exterior

Lake George Water Front Cabin Spectacular Views

Lake George Water Front Cabin Spectacular Views
Ticonderoga
9.6 out of 10, Exceptional, (35 reviews)
"Super pretty views and a very quiet and tranquil stay :)"
United States
Mackenzie C.
The price is HK$5,082
HK$9,918 total
includes taxes & fees
6 Jun - 7 Jun
Lake George Water Front Cabin Spectacular Views
Exterior detail

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
The price is HK$1,331
HK$1,869 total
includes taxes & fees
16 Jun - 17 Jun
Handcrafted mountain cabin with gorgeous views
Outdoor dining

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)
" The host was very helpful, the camp was awesome the views of the mountains were very good and the hot tub was a great time!!!"
United States
Beth S.
The price is HK$1,292
HK$1,886 total
includes taxes & fees
25 May - 26 May
Camp Lillian Gorgeous New Cabin with Mountain Views
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

Lodges At Cresthaven

Lodges At Cresthaven

10/10 Excellent
"The room was beautiful and the view was spectacular."
Farima 1-night trip
Posted 4 hours ago
Lodges At Cresthaven

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 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?

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

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?

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 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.