165+ Hotel & Resort Deals in Chestertown |
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Chestertown Hotels, Resorts, and Rentals

About Chestertown Vacation Rentals

There are more than 165 places to stay in Chestertown that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chestertown.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chestertown, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chestertown. Places to stay near Chestertown are 1185.92 ft² on average, with prices averaging US $369 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chestertown with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chestertown

Type Count
Vacation Homes 103
Cabin Rentals 19
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: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay 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

Stay Near Chestertown's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Chestertown's top attractions, neighborhoods, and points of interest.


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 Hotels, Resorts, and Rentals Nearby 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 hotels or resorts in Chestertown?

You have a lot of choices in or near Chestertown. If you need a hotel in the Chestertown area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chestertown:

How many vacation rentals have private pools in Chestertown?

There are 2 accommodation options with private pools in or near Chestertown. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 165 in the Chestertown area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chestertown.

Nearby Neighborhood (2) 
Neighborhood Property Count
Chester Shores Hotel & Resort Deals in Lake George, New York 127
Friends Lake Inn Hotel & Resort Deals in Lake George, New York 129

People Also Ask

There are 4 hotels in Chestertown 1 resorts, and 131 rentals

Recently Booked Hotels, Resorts, or Rentals in Chestertown