166+ Luxury Vacation Rentals & Cabins in Chestertown |
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  2. New York
  3. Lake George
  4. Chestertown

Chestertown Cabin Rentals

About Chestertown Vacation Rentals

There are more than 166 incredible getaway rentals that are available in Chestertown. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Chestertown.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Chestertown, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Chestertown. Places to stay near Chestertown are 1128.24 ft² on average, with prices averaging CA $517 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Chestertown. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Chestertown

Type Count
Vacation Homes 104
Cabin Rentals 20
Cottages 11
Holiday Apartments 9
Ski Chalet Rentals 3
B&B 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chestertown with Cabinns.ca.

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

Activities Chestertown Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Chestertown. Discover Top Attractions For Your Next Outdoor Adventure.


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

Find Nearby Cabin Rentals in these Cities & Neighborhoods


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 cabins, lake houses & summer homes in Chestertown?

We provide an array of great vacation destinations in Chestertown. If you are looking to stay in or around the Chestertown area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chestertown:

How many cabin rentals and resorts have private pools in Chestertown?

We have 2 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Chestertown. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Chestertown is best for families?

Searching for a family-friendly cabin in Chestertown? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Chestertown?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 166 in the Chestertown area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Chestertown.

Nearby Neighborhood (2) 
Neighborhood Property Count
Chester Shores Rental Cabins and Private Getaways in Lake George, New York 127
Friends Lake Inn Rental Cabins and Private Getaways in Lake George, New York 129

People Also Ask

There are 3 hotels in Chestertown 1 resorts, and 133 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Chestertown