Find & compare ski resorts in Chestertown, NY from $526

Name: Friends Lake Inn
Rating: 8.6

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Top Chestertown Ski Resorts and Hotels

The Fern Lodge

46 Fiddlehead Bay Rd. Chestertown NY

$473 nightly

$526 total

Dec 12 - Dec 13

Total with taxes and fees

This bed & breakfast's 8 hot tubs and gym are among the featured amenities. Enjoy the sauna and free perks like local cuisine breakfast and free self parking. ...

Friends Lake Inn

963 Friends Lake Rd Chestertown NY

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A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, ...

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

It’s that time of the year—the mountains are calling and you are ready to hit the slopes. There’s no better place than ski hotels in Chestertown. With access to various places to ski, from bunny hills for the newbies to black diamonds for the experts, Chestertown ski resorts are your best bet to enjoy some wintry fun.

If you're a beginner skier and want to start with a few trips down the bunny slopes, see if your Chestertown ski hotel or the nearby facilities offer lessons. If you're a veteran on the slopes, take the chair lift up to the top of the mountain and take in the views as you slalom down the fresh snow. After a full day on the slopes, retreat to your Chestertown ski resort to warm up. Take a dip in the hot tub on property, drink some cocktails at the lobby bar to warm you up or get cozy in your hotel room and order room service.

Travelocity is here to help you find the best deals on Chestertown ski hotels and resorts, so you can hit the ski lift without breaking the bank! Book today and Wander Wisely.