Photo by Julie Miller

Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (151)
"This is our third time staying at this property. Each and every time, I am so sad to leave. The hosts are fantastic and answer promptly any questions we may have. This property is so beautiful and we can't wait to come back again next spring."
Walk to Million Dollar Beach from this awesome Cottage!

Bolton Landing Mountain House!

8.8 out of 10, Excellent, (6)
"Beautiful house! Kids and adults loved it. Crappy weather let us inside which did not disappoint. Host was so quick to respond to my messages "
The price is €914
includes taxes & fees
22 Feb - 23 Feb
Bolton Landing Mountain House!

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (48)
"The house was very cute. We enjoyed our stay. "
The price is €159
includes taxes & fees
26 Feb - 27 Feb
Adirondack Bungalow Getaway

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

10.0 out of 10, Exceptional, (75)
"My family and I loved the stay. Great place to enjoy the nature. The house had everything we needed such as great kitchen, fireplace, and jacuzzi. "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (7)
"Owners were very friendly and had everything you could think of, including local trails, equipment to go out on the lake which was included with the cabin games, local eats, etc."
The price is €177
includes taxes & fees
23 Feb - 24 Feb
Trout House Village Resort

PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events

9.0 out of 10, Wonderful, (52)
"Loved our stay in February, very close to skiing at Gore. House had enough supplies in the kitchen to make it easy for us to cook for the 7 of us who stayed. (There is not much in the way of restaurants in the area, especially open mid-week.) Vasili was quick to answer any questions I had, accessing the house was a breeze, and everything went smoothly during our stay."
PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events

Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

9.6 out of 10, Exceptional, (160)
"Actually had more room than I thought, we could have fit another 2 people in there! Very spacious. Photos on the website are a little outdated since the TVs have been upgraded since. There were some questionable items like piles of sheets on the floor that looked like they where not cleaned or doors to the closets that where falling off. The master bed rooms remote to the tv was no where to be found so didn't get to use that. But the communication with the host was great. Our safety of making it...
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

Lakefront home private beach on Schroon Lake

9.6 out of 10, Exceptional, (21)
"We are incredibly grateful to have been able to rent this house for our wedding. The house allowed us to have plenty of room for family to stay and everyone to get ready. The beach was perfect with gorgeous views as our backdrop. Our concerns were minor, and Lorraine was very responsive, kind and accommodating. "
Lakefront home private beach on Schroon Lake

Beautiful cottage on quiet country road walking distance to charming North Creek

9.8 out of 10, Exceptional, (34)
"We loved the cottage from the moment we pulled into the driveway. The location was ideal. The interior of the cottage was warmly decorated. It was clear that the owners have an eye for detail and a gift for creating such a cozy and welcoming place. There was plenty of room to cook and relax. We hope to visit again. Thank you. "
The price is €211
includes taxes & fees
4 Mar - 5 Mar
Beautiful cottage on quiet country road walking distance to charming North Creek

Handcrafted mountain cabin with gorgeous views

9.8 out of 10, Exceptional, (41)
"Just as described. Loved the cabin. Beautiful views. Perfectly stocked with cooking utensils and pans that finally aren’t beat up teflon. One of the best rentals we have ever stayed in. Hot tub was a huge plus. Looking forward to returning. "
The price is €208
includes taxes & fees
24 Feb - 25 Feb
Handcrafted mountain cabin with gorgeous views

Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

9.2 out of 10, Wonderful, (94)
"Warm and family friendly "
Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

The Owl of Lake George 2 BR deck lake views fireplace

9.0 out of 10, Wonderful, (11)
"The cabin was fantastic. Would have been nice to have a working fire place and pit. This was expected to enjoy the full experience. We still enjoyed the stay. Thank you"
The Owl of Lake George 2 BR deck lake views fireplace

Terrace on the Lake, Spectacular Large Home with Private Beach

10.0 out of 10, Exceptional, (305)
"We stayed at Terrace on the Lake with several friends and their families and had a great time! The house was clean and had everything we needed--including space for the kids to play. Since it was winter we also appreciated the proximity to Gore Mountain. "
Terrace on the Lake, Spectacular Large Home with Private Beach

Hickory Hill Mountaintop charming family friendly quiet very private lake view

10.0 out of 10, Exceptional, (128)
"Had a wonderful time with friends. Location was spacious and quite. Great views of the lake. House had everything we needed. Hope to stay here again in the future "
Hickory Hill Mountaintop charming family friendly quiet very private lake view

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (82)
"Amazing"
The price is €202
includes taxes & fees
26 Feb - 27 Feb
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

9.8 out of 10, Exceptional, (85)
"Close to gore, on nice dirt road along brook, rustic but cute"
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

10.0 out of 10, Exceptional, (11)
"Fantastic experience from start to end! Very new and upscale remodel with an open floor concept. Large lot with plenty of parking, basketball, patio dining, firepit, and grill. Very cool screened in porch overlooking the lake. Plenty warm and excellent water pressure. There's also a bar/restaurant right next door which was very convenient. Five stars! "
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
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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Other types of properties in Chestertown you may be interested in

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

3.0 star property
9.2 out of 10, Wonderful, (1006)
"😊"
The price is €103
includes taxes & fees
27 Feb - 28 Feb
Holiday Inn Resort Lake George - Adirondack Area by IHG

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1226)
"Very Nice"
The price is €108
includes taxes & fees
23 Feb - 24 Feb
The Queensbury Hotel
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.

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 patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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. Loon Lake and Hudson River 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.