Photo by Julie Miller

Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

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

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

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

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 AU$292
includes taxes & fees
18 Feb - 19 Feb
Trout House Village Resort

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (48)
"The house was very cute. We enjoyed our stay. "
The price is AU$259
includes taxes & fees
26 Feb - 27 Feb
Adirondack Bungalow Getaway

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 AU$346
includes taxes & fees
23 Feb - 24 Feb
Beautiful cottage on quiet country road walking distance to charming North Creek

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

10.0 out of 10, Exceptional, (19)
"Everything about this property is how it should be and accommodating small animals is even a bonus. The owners/hosts are easy to communicate w and eager to make your stay comfortable. Everything extra you may need is here. Thank you to the Kiel’s! "
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (82)
"Amazing"
The price is AU$328
includes taxes & fees
23 Feb - 24 Feb
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

9.6 out of 10, Exceptional, (41)
"Amazing view from the back deck, very clean home, plenty of room for our family of 6. Will definitely be staying here again next time we're in Lake George!"
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

9.8 out of 10, Exceptional, (310)
"We rented the house for a weekend to accomodate a large group and the house was perfect for that purpose. The home was clean and we woke up to amazing mountain and river views. The common areas were spacious and the kitchen was large and had everything we needed for a fun weekend. The only draw back to the house was that you can hear the people walking above you from the upstairs or the main floor which can make for an early rising in the AM. Other than that the home is perfect and I highly...
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Terrace on the Lake, Spectacular Large Home with Private Beach

10.0 out of 10, Exceptional, (304)
"This was the best weekend and the best accomodations! It was incredibly clean and we were all comfortable. They had everything we needed and more. "
Terrace on the Lake, Spectacular Large Home with Private Beach

Quiet Cabin on Glen Lake w/ Boat Dock & Deck!

8.8 out of 10, Excellent, (16)
"Nice location near lake George village and amenities. Beautiful view, lots of Eagles and Osprey. Plenty of room. Decent fishing on Glen Lake. Recommended for peaceful getaway. "
Quiet Cabin on Glen Lake w/ Boat Dock & Deck!

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.

Cozy South Bay Cabin w/ Lake & Mountain Views

9.8 out of 10, Exceptional, (17)
"Amazing piece of property, beautiful views, and direct access to water, Cabin is very clean and offers everything needed for a comfortable stay. A fishermans paradise. Will book again for sure !!"
Cozy South Bay Cabin w/ Lake & Mountain Views

Housekeeping Cottage - near Lake George & Adirondacks - Belmont Special June 3-8

10.0 out of 10, Exceptional, (33)
"Stayed for 4 nights. We didn’t spend a lot of time in the cottage, but it was pefect for us. Great location"
Housekeeping Cottage - near Lake George & Adirondacks - Belmont Special June 3-8

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!

Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

8.6 out of 10, Excellent, (11)
"Nice waterfront location "
Direct lakefront cottage with wood burning fireplace in great room. Pet 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

Cozy, pet friendly cabin minutes to lake George village

8.8 out of 10, Excellent, (20)
"Excellent location! Minutes to restaurants and shops! Very nice rental! "
Cozy, pet friendly cabin minutes to lake George village
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, (1004)
"😊"
The price is AU$176
includes taxes & fees
25 Feb - 26 Feb
Holiday Inn Resort Lake George - Adirondack Area by IHG

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1230)
"Great customer service. Chris at front desk was really professional and make sure our stay was comfortable. Great breakfast and tasty food. "
The price is AU$179
includes taxes & fees
17 Feb - 18 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 61 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.