Photo by Julie Miller

Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access

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

10.0 out of 10, Exceptional, (53)
"Host John was like best of friends. Couldn’t have done more for us. Sue too was very nice. Pearl and ruby, their do"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Private child-friendly home with game room, high-speed WiFi, and wraparound deck

9.8 out of 10, Exceptional, (54)
"We enjoyed our stay at this beautiful property so much! We may have to return next time we are in the area. It had everything we needed, including a wide variety of kitchen supplies. The kids enjoyed the basement activities (ping pong especially!). We loved how secluded it was but also easy to get to nearby towns."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck

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

10.0 out of 10, Exceptional, (69)
"We were looking for something for our “baby moon” before I go back to work. We had a dream checklist and this home checked off everything on our list. We brought our 3mo old and our dog and had a peaceful weekend enjoying the hot tub, the Blackstone, and the cozy fireplace. We had some questions that were answered immediately. Can’t wait to go back with friends when it’s warmer not enjoy the pool and yard more! Love love lovd"
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Terrace on the Lake, Spectacular Large Home with Private Beach

10.0 out of 10, Exceptional, (301)
"The space is great for a family gathering. Spacious shared spaces and comfortable bedrooms. "
Terrace on the Lake, Spectacular Large Home with Private Beach

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

10.0 out of 10, Exceptional, (301)
"Beautiful log home in a quiet neighborhood right on the river. Such a nice home. Highly recommend you stay here. Great for large family gatherings. "
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Cottage - near Lake George & Adirondacks - year round

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"
Cottage - near Lake George & Adirondacks - year round

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

9.2 out of 10, Wonderful, (93)
"Beautiful property and location is ideal for a getaway "
Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

3 Bedroom Adirondack Cabin 400m From Lake, 10 min to Lake George, 20 to Saratoga

8.8 out of 10, Excellent, (8)
"A nice weekend getaway! Enjoyed the fireplace and outside fire pit. Host was very accommodating and helpful with local restaurant suggestions and more. Thank so much!"
3 Bedroom Adirondack Cabin 400m From Lake, 10 min to Lake George, 20 to Saratoga

Lakefront luxury, Lake George log cabin home with your own private sandy beach

9.8 out of 10, Exceptional, (13)
"Wonderful trip with friends for our annual kid free weekend! Excellent location with beautiful views! Great location and close enough to village for easy access to restaurants and shopping. "
Lakefront luxury, Lake George log cabin home with your own private sandy beach

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (80)
"Spent 7 days/6 nights in our cabin. We brought our dog, Sheilah. Clearing around the cabin was a perfect place for a well behavedo my y WeWe’re"
The price is €208
includes taxes & fees
25 Nov - 26 Nov
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

Camp Lillian Gorgeous New Cabin with Mountain Views

10.0 out of 10, Exceptional, (61)
"We use this cabin as a base for exploring south Adirondack hiking trails. We really enjoy the location, the cabin itself, the quiet place and the scenery at diner time after long hike. One of our favorite was very near by : Peaked mountain trail."
The price is €208
includes taxes & fees
25 Nov - 26 Nov
Camp Lillian Gorgeous New Cabin with Mountain Views

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

2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!

8.6 out of 10, Excellent, (24)
"We thought the property was nicely decorated. Everything was functional and a good condition. At the time of the year we were going the pool was not an issue."
2 STORY ADIRONDACK LOG CABIN-SKI ! SKI! SKI!

Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay

9.8 out of 10, Exceptional, (106)
"This home is very clean and conveniently located within the Adirondacks. Close to towns with lots of dining and shopping options. Nice beach for the neighborhood, close and easy walking distance. "
Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay

Lake George Great Location with Lake Access

10.0 out of 10, Exceptional, (12)
"Right next to the lake!"
Lake George Great Location with Lake Access

Log Cabin on the Hudson

9.8 out of 10, Exceptional, (86)
"Our family absolutely loved our stay! The house is so beautiful! The kids loved the playground. We all loved making s’mores at the fire pit. The house was big enough to comfortably accommodate our family of 9. The house is in a private wooded area with the river across the road. You can not see the neighbors once you are on the property. It was only 20 minutes away from downtown Lake George. We are definitely planning on staying at this house again next time we go on vacation. "
Log Cabin on the Hudson

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

Cabin, lake and moose...OH MY!!

10.0 out of 10, Exceptional, (36)
"This cabin was very comfortable and had everything we wanted and expected. It is located at the top of a steep driveway but we had no problem with our four wheel drive Jeep. The yard is down some steps to the front of the home. Home was nicely decorated and beds were cozy and comfortable. One bathroom but spacious with a nice shower. Kitchen was large and had everything we needed to cook. The home is a bit remote from restaurants so plan for some meals after a day on the lake. Lake access...
Cabin, lake and moose...OH MY!!
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

Six Flags Lodge & Indoor Waterpark

3.5 star property
7.8 out of 10, Good, (1020)
"A great stay. Staff very friendly. "
The price is €167
includes taxes & fees
8 Dec - 9 Dec
Six Flags Lodge & Indoor Waterpark

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1193)
"it was a great experience "
The price is €109
includes taxes & fees
25 Nov - 26 Nov
The Queensbury Hotel

La Quinta Inn & Suites by Wyndham Lake George

2.0 star property
9.0 out of 10, Wonderful, (1503)
"Very nice hotel. Only issue were the tons of kids running around unattended … they were in the fitness room, dripping wet from the pool with no shoes on and no adults watching them. "
The price is €105
includes taxes & fees
3 Dec - 4 Dec
La Quinta Inn & Suites by Wyndham Lake George
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?

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub! : This holiday home rental outside of Chestertown is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 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 selection of games and 1 hot tub.

How many holiday rentals will I find in Chestertown?

With 59 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.