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Featured Chester Ski Hotels

See all 95 Hotels in Chester
Chester House Inn

Chester House Inn

266 Main St, Chester
4.1 out of 5 (13 reviews)
Felt right at homeInnkeeper Bob made us feel right at home at Chester House Inn. A classic New England style inn with all the charm and history you could want. Plus a tasty breakfast and perfect location for winter sports!
  Feb 6, 2017

$139

$139
Rose Arbour Bed & Breakfast

Rose Arbour Bed & Breakfast

55 School Street, Chester
2.5 out of 5.0
3.7 out of 5 (18 reviews)
Cute VictorianSuzie was a congenial and accommodating host. Her scones are excellent. They compare very favorably with what we've had in England! Very pleasant stay.
  Aug 21, 2017

$85

$85
The Karass Inn

The Karass Inn

225 Pleasant Street, Chester
3.0 out of 5.0
4.9 out of 5 (8 reviews)
Karass Inn(credible)We booked the Karass Inn on a whim during an extended weekend jaunt through New England. We wanted a quaint (my wife's word) place to rest our head for the Vermont leg of our leaf peeping journey - the Karass provided. The Innkeeper was a pleasant and accommodating (bonus points for providing us ...
  Oct 17, 2017

$109

$109
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Chester Ski Resorts Information

Carve up the slopes with reservations at Chester ski resorts.
  • Check out our impressive variety of ski lodges
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Strap on your ski boots, slip into your snow pants, and brave the fresh powder on black diamond trails when you make reservations here on Expedia.com. Our Chester ski hotels turn up the heat on your adventures at the chilly slopes.

Whether you’re flaunting your Shaun White-inspired half-pipe tricks or still trying to figure out how to do a “pizza,” book a stay at a ski-in-ski-out resort. There’s nothing better than staying at a Chester ski hotel right on the slopes to easily access both the chair lift and hot chocolate in the lodge. After sledding, cross-country skiing, and snowshoeing in Chester, cozy up around the fireplace in your ski chalet.

Calling all ski bunnies and snowboarding pros: we offer deals on ski resorts in Chester here on Expedia. You’ll slide right into our unbeatable deals with a ton of hotels to choose from and personalized recommendations to help you create the perfect mountain trip. Spend more of your hard-earned cash on new gear for your adventures skiing in Chester and less on your accommodation. From accommodations with fireplaces to rooms with a view of the trails, we have a ski hotel meeting all your needs and price range. Book one of 95 ski hotels today and get ready to carve up the slopes tomorrow.