Chestertown Hotels

THE 10 BEST Hotels in Chestertown 2024

Chestertown Hotels

and Places to Stay
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Distance from

25 mi

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13 properties in Chestertown
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    Properties ranked using exclusive Tripadvisor data, including traveler ratings, confirmed availability from our partners, prices, booking popularity and location, as well as personal user preferences and recently viewed hotels.
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    Highest rated hotels on Tripadvisor, based on traveler reviews.
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This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Small Hotel
#2 Best Value of 13 places to stay in Chestertown
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
#13 Best Value of 13 places to stay in Chestertown
No other properties are available in Chestertown. View nearby results below.
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This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
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Cabin/Campground

Chestertown Hotels Information

Hotels in Chestertown

13

Hotels Prices From

$188

Hotels Reviews

811

Hotels Photos

831

Travel high season

Dec - Feb

Travel low season

Jun - Aug

High season avg price

$400

Low season avg price

$248
Not sure when to visit?
Price trends, weather and things to do can help you make a decision.
Season
Avg. price/night
Avg. temperature
Avg. precipitation
Dec - Feb
Avg. price/night
$398
HIGHEST
$176$599
Avg. temperature
22ºF
COLDEST
-16ºF93ºF
Avg. precipitation
32in
DRIEST
26 in48 in
Mar - May
Avg. price/night
$364
$176$599
Avg. temperature
43ºF
-16ºF93ºF
Avg. precipitation
34in
26 in48 in
Jun - Aug
Avg. price/night
$248
LOWEST
$176$599
Avg. temperature
68ºF
WARMEST
-16ºF93ºF
Avg. precipitation
45in
WETTEST
26 in48 in
Sep - Nov
Avg. price/night
$298
$176$599
Avg. temperature
48ºF
-16ºF93ºF
Avg. precipitation
38in
26 in48 in
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Chestertown. Select dates and complete search for nightly totals inclusive of taxes and fees.

Hotels near the sights

  • C&C Snowmobile Tours
    Experience the excitement & adventure of snowmobiling with New York's newest and most experienced snowmobile tour. Our staff of C+C Adirondack Snowmobile Tours has a combined 40+ years riding on the trails, so get ready for an exciting trip. We offer a range of riding that is suited for everyone from the beginner to the most advanced rider.
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  • The Crossroads
    We have a little of everything here at The Crossroads Deli and Cafe: We brew the best coffee around: fair trade organic coffee from Deans's Beans and Barkeater Coffee Co. Breakfast sandwiches are made fresh every morning. Our subs and sandwiches are made fresh to order with Boar's Head Meats and Cheese. We also have homemade soups and salads daily. Eat in at one of our tables or call an order in to take with you. Sporting Goods: Anything you need for the Great Outdoors! Whether you are hunting, fishing, headed to the lake or up a high peak; we have what you need. Sporting licenses, fishing and fly fishing equipment, live bait, lures, camping gear, axes and knives, snowshoes, and hunting supplies for any season. We buy and sell new and used guns. Clothing and Footwear: Woolrich, Carhartt, Columbia, Johnson Woolen, Outdoor Research, Red Ledge, Keen, Teva, Minnetonka, Georgia, Rocky, Bogs, Buff: If you are hiking, hunting, fishing, working, or enjoying the outdoors; we have what you need to stay warm and dry or cool and happy. Adirondack Books, Gifts, and Candy: Something for everyone! Locally made chocolates and candy, maple syrup, peanut butter, spices, gifts, books, and prints by local photographers. Craft Beer: We have a fantastic selection of craft beer, always updating and changing with the seasons. Ice Cream and Stand Up Paddleboards: When the weather is warm, come visit our soft serve stand and try one of our SUP's.
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  • Rustic Charm
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  • Circle B Ranch
    Circle B Ranch has been family owned and operated since 1961. Prior to 1961 the ranch was known as "Circle R At Circle B Ranch we specialize in Guided Trail Rides through the Mighty Adirondack Forrest on more than 500 acres. We offer 1 hour, 2 hour and 3 hour rides from beginner to experienced riders. New for 2019 our recently completed beaver pond trail takes you over two working beaver dams, across potter brook via bridge to a stunning Adirondack marsh vista. Also new and improved for 2019 are our Mountain Lookout Trail & Fawn Ridge Preserve Trail. Each trail offers riders with a different perspective of the Adirondack landscape. In the winter months we offer Horse Drawn Sleigh Rides both group and private in our antique sleighs complete with stunning mountain views. Our private rides are great for couples wishing for a romantic outing. During the spring, summer and fall we offer hay rides. Great for small or large groups that wish to experience the beauty of the Adirondacks.
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Frequently Asked Questions about Chestertown hotels

The Alpine Lodge, Gore Mountain Lodge, and Friends Lake Inn are some of the most popular hotels for travelers looking to stay near C&C Snowmobile Tours. See the full list: Hotels near C&C Snowmobile Tours.

Popular hotels close to Rustic Charm include The Alpine Lodge, Gore Mountain Lodge, and Friends Lake Inn. See the full list: Hotels near Rustic Charm.

Popular hotels close to Albany Intl Airport include Tru by Hilton Albany Airport, Hilton Garden Inn Albany Airport, and Albany Airport Inn and Suites. See the full list: Hotels near Albany Intl Airport.

The above hotel descriptions were created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for any of the above hotel descriptions. Please read full traveler reviews for more details and information. If you believe something in one of these AI-generated descriptions is inaccurate, please share your feedback.