166+ Vacation Rentals in Chestertown |
  1. USA
  2. New York
  3. Lake George
  4. Chestertown

Chestertown Vacation Rentals, Hotels, & Places to Stay

About Chestertown Vacation Rentals

There are more than 166 places to stay that are available in Chestertown. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Chestertown.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. 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 Varoom's places in Chestertown, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Chestertown. Places to stay near Chestertown are 1128.24 ft² on average, with prices averaging US $370 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Chestertown. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Chestertown

Type Count
Vacation Homes 104
Cottages 11
Holiday Apartments 9

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Chestertown today.

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

Varoom 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 vacation rentals in Chestertown?

We have scoured the web to find you options in Chestertown. If you plan on staying near or in the Chestertown area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the the Top Places to Stay in Chestertown:

How many vacation rentals have private pools in Chestertown?

We have found 1 places to stay that feature a private swimming pool in or near Chestertown. Some of the best places to stay that feature or have access to a swimming pool are:

Which vacation homes in Chestertown are best for families?

If you are looking for a place to stay that is family-friendly in Chestertown, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Chestertown:

How many Varoom vacation rentals are available in Chestertown?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 166 in the Chestertown area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay 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 166 Chestertown, NY Vacation Rentals

Recently Booked Vacation Rentals in Chestertown