167+ Private Villas and Holiday Rentals in Chestertown |
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  2. New York
  3. Lake George
  4. Chestertown

Chestertown Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chestertown

Discover more than 167 vacation rentals available in Chestertown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chestertown.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chestertown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chestertown. On average, places to stay near Chestertown offer 1190.09 ft², with nightly prices averaging CA $510.

With Casai, finding and comparing holiday rentals in Chestertown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Chestertown

Type Count
Vacation Homes 105
Cottages 11
Holiday Apartments 9

Use these Quick Filters to Find a Holiday Rental in Chestertown

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chestertown.

Weather in Chestertown, NY

View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chestertown, NY

Casai offers a large selection of top attractions around Chestertown . Research things to do on your vacation before you visit Chestertown.


Friends Lake
Loon Lake Beach
Tripp Pond
Loon Lake
Gore Mountain Ski Resort
Outlets at Lake George
Great Escape and Splashwater Kingdom
Fort William Henry
West Mountain Ski Resort
Million Dollar Beach
Lake George Dog Beach
Shepard's Beach Park
Lake George Steamboat Company
Adirondack Outlet Mall
Cool Insuring Arena
Lake George Shoreline Cruises
Magic Forest Family Fun Park
Charles R. Wood Theater
Hickory Ski Center
Wild West Ranch and Western Town

Other Places to Stay in Chestertown, NY


Friends Lake Inn 129 Properties
Loon Lake Beach 129 Properties
Chester Shores 127 Properties
Loon Lake 106 Properties
Friends Lake 99 Properties
Tripp Pond 56 Properties

Frequently Asked Questions About Chestertown?

What are the top holiday rentals in Chestertown?

With numerous options available in Chestertown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chestertown:

How many holiday rentals have private pools in Chestertown?

Discover a selection of holiday rentals with private pools near Chestertown with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chestertown are best for families?

If you're searching for a family-friendly holiday home in Chestertown, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chestertown:

How many Casai.ca holiday rentals are available in Chestertown?

As of 2025, Casai boasts over 167 properties listed in the Chestertown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chestertown.

Nearby Neighborhood (2) 
Neighborhood Property Count
Chester Shores Vacation Rentals in Lake George, New York 127
Friends Lake Inn Vacation Rentals in Lake George, New York 129

People Also Ask

There are 167 Chestertown, NY Holiday Rentals

Recently Booked Holiday Rentals in Chestertown