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

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chestertown vacation rentals

Egyptian cotton sheets, premium bedding, individually decorated

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.6 out of 10, Exceptional, (24 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
Trout House Village Resort
Interior

Boat, Fish, Hike! Schroon Lake Getaway

Boat, Fish, Hike! Schroon Lake Getaway
3.0 star property
Schroon Lake
The price is P11,097
P13,387 total
includes taxes & fees
Jul 1 - Jul 2
Boat, Fish, Hike! Schroon Lake Getaway
WiFi

Lake George Escape - Campground

Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very Good, (178 reviews)
"We had a great stay at Lake George Escape Campground! The campground was clean, peaceful, and well maintained. Our cabin was comfortable, the staff was friendly, and there was plenty to do throughout our stay. We loved the atmosphere and made some great memories. We will definitely be back and highly recommend it to anyone visiting the Lake George area!"
United States
Alana
The price is P17,562
P19,494 total
includes taxes & fees
Jun 29 - Jun 30
Lake George Escape - Campground
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 P23,175
P25,724 total
includes taxes & fees
Jul 1 - Jul 2
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 P17,701
P54,899 total
includes taxes & fees
Jul 13 - Jul 14
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Interior

Cozy Room Near Schroon Lake Marina, Town & Beach!

Cozy Room Near Schroon Lake Marina, Town & Beach!
3.0 star property
Schroon Lake
The price is P8,461
P10,408 total
includes taxes & fees
Jun 29 - Jun 30
Cozy Room Near Schroon Lake Marina, Town & Beach!
Interior

Easy Schroon Lake Living! Close to Marina & Town

Easy Schroon Lake Living! Close to Marina & Town
3.0 star property
Schroon Lake
The price is P8,461
P10,408 total
includes taxes & fees
Jun 29 - Jun 30
Easy Schroon Lake Living! Close to Marina & Town
Interior

Close to Marina, Beach & Town! Schroon Lake Escape

Close to Marina, Beach & Town! Schroon Lake Escape
3.0 star property
Schroon Lake
The price is P8,461
P10,408 total
includes taxes & fees
Jun 29 - Jun 30
Close to Marina, Beach & Town! Schroon Lake Escape
Front of property

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 P8,461
P10,408 total
includes taxes & fees
Jun 29 - Jun 30
Walk to Schroon Lake! Studio w/ Shared Fire Pit
Interior

Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
The price is P8,461
P10,408 total
includes taxes & fees
Jun 29 - Jun 30
Schroon Lake Room < 1 Mi to Marina & Beach!
Interior

< 1 Mi to Boat Launch! Schroon Lake Basecamp

< 1 Mi to Boat Launch! Schroon Lake Basecamp
3.0 star property
Schroon Lake
The price is P11,097
P13,387 total
includes taxes & fees
Jun 29 - Jun 30
< 1 Mi to Boat Launch! Schroon Lake Basecamp
Interior

9 Mi to Lake George Village: Home in Queensbury

9 Mi to Lake George Village: Home in Queensbury
3.0 star property
Queensbury
4.0 out of 10, (1 review)
"The house was a bit old-fashioned, but spacious. There were issues with cleanliness and attention to detail, and the apparent lack of effort and investment was quite a disappointment. If the house were better cared for, and if some effort were put into a couple of improvements, it could’ve been a comfortable stay, but cleanliness and attention to basic necessities should be met at minimum for a place that you’ll be sleeping or showering."
United States
Kathryn
The price is P11,097
P28,968 total
includes taxes & fees
Jul 19 - Jul 20
9 Mi to Lake George Village: Home in Queensbury
Interior

Boat, Fish & Hike! All-season Schroon Lake Getaway

Boat, Fish & Hike! All-season Schroon Lake Getaway
3.0 star property
Schroon Lake
The price is P8,461
P10,408 total
includes taxes & fees
Jul 6 - Jul 7
Boat, Fish & Hike! All-season Schroon Lake Getaway
Interior

Warrensburg Home ~ 6 Mi to Lake George!

Warrensburg Home ~ 6 Mi to Lake George!
3.0 star property
Warrensburg
10.0 out of 10, Exceptional, (1 review)
The price is P38,073
P63,073 total
includes taxes & fees
Jul 6 - Jul 7
Warrensburg Home ~ 6 Mi to 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.
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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

8/10 Good
"The rooms are clean and they are dog friendly. The pool was perfect for my child. This hotel is close to the outlets. The breakfast was okay."
Jennifer 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Lake George

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 vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

How many vacation rentals will I find in Chestertown?

With 60 Expedia vacation rentals, you're sure 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 vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.