Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Chestertown vacation rentals

Cabin, 1 Bedroom, Non Smoking, Lake View | 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 ￥23,441
￥29,938 total
includes taxes & fees
May 31 - Jun 1
Trout House Village Resort
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 ￥19,115
￥21,218 total
includes taxes & fees
May 12 - May 13
Lake George Escape - Campground
Apartment (0 Bedroom) | 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 ￥13,474
￥22,264 total
includes taxes & fees
May 10 - May 11
< 1 Mi to Boat Launch! Schroon Lake Basecamp
Corner Cottage | Living area | Flat-screen TV

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 ￥31,054
￥34,471 total
includes taxes & fees
Jun 9 - Jun 10
Beach Cottages at Lake George
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 ￥49,354
￥54,783 total
includes taxes & fees
May 11 - May 12
The Elms Waterfront Cottages
House, 5 Bedrooms | 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 ￥35,451
￥126,038 total
includes taxes & fees
May 27 - May 28
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
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

Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George

10/10 Excellent
"room clean and spacious. pool one of cleanest I've ever seen. Breakfast ok. many choices just not many I liked. Nice fire pit in the evening. If you want your room cleaned every day and clean towels. your need to let staff know. it's done every other day. "
Kim 2-night trip
Posted 5 hours ago
Hampton Inn & Suites 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:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • 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 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.

What are some of the best vacation home rentals in Chestertown?

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

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.