Book the Best Chester Ski Hotels in 2026 from CA $118

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Our top choices for Chester ski hotels

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

1. Fullerton Inn

Chester Depot

CA $199 total

includes taxes & fees

Nov 10 - Nov 11

A cozy cabin interior with a wooden ceiling, a sofa, a red armchair, a small table with magazines, and a window with curtains.

2. Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!

Andover

CA $598 total

includes taxes & fees

Nov 10 - Nov 11

A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

3. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Andover

CA $946 total

includes taxes & fees

Nov 10 - Nov 11

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

4. Best Western Springfield Hotel

Springfield

CA $236 total

includes taxes & fees

Nov 16 - Nov 17

A large two-story house with a front porch and a well-maintained lawn.

5. The Landgrove

Londonderry

CA $258 total

includes taxes & fees

Nov 16 - Nov 17

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

6. The Upper Pass Lodge at Magic Mountain

Londonderry

Slope-side tranquility awaits at Magic Mountain, where ski-in access meets cozy mountain lodge comfort just steps from powder perfection.

CA $136 total

includes taxes & fees

Nov 16 - Nov 17

A rustic dining area with wooden beams, tables, chairs, and a fireplace.

7. The Inn at Weathersfield

Perkinsville

Alpine ski retreat nestled in Vermont mountains offers cozy luxury with nearby cross-country and downhill adventures.

CA $361 total

includes taxes & fees

Nov 29 - Nov 30

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

8. Pointe at Castle Hill Resort

Cavendish

Winter wonderland awaits at this mountain retreat, offering direct access to Okemo resort with shuttle service and spa relaxation.

CA $219 total

includes taxes & fees

Nov 17 - Nov 18

A modern outdoor lounge area with two lounge chairs and a wooden deck.

9. Otherland Hotel

Newfane

CA $225 total

includes taxes & fees

Nov 10 - Nov 11

A large stone building with a steep roof, surrounded by dense forest and hills.

10. Castle Hill Resort And Spa

Cavendish

Mountain majesty meets adventure at this historic luxury hotel, where Okemo Mountain skiing awaits after spa indulgence.

CA $257 total

includes taxes & fees

Nov 10 - Nov 11

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Choose what matters most at ski hotels in Chester

Resort

4 stars

Top Chester Hotel Reviews

Fullerton Inn

Chester Depot

10/10 Excellent

Marian

The Inn at Weathersfield

Perkinsville

10/10 Excellent

WilliamWoodwort

Best Western Springfield Hotel

Springfield

10/10 Excellent

tim

A rustic lodge with stone walls, a stone fireplace, and outdoor seating.

Seesaw's Lodge

Peru

10/10 Excellent

We enjoyed our stay immensely! Our room was lovely and clean. The pillows and bed were very comfortable! The Green Mountain coffee in our room was a nice touch! Our only complaint was that there wasn’t real cream for our coffee, so next time, we will bring our own. The large walk-in shower was very nice as well. The main common area was beautiful and homey! The kitchen seemed fully equipped, but we didn’t have any meals there. We will definitely come back for a longer stay!

Joy