Book the Best Chester Ski Hotels in 2026 from CA $117

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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 $196 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Andover

CA $936 total

includes taxes & fees

Nov 6 - Nov 7

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

3. Best Western Springfield Hotel

Springfield

CA $234 total

includes taxes & fees

Nov 12 - Nov 13

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.

4. 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 $137 total

includes taxes & fees

Nov 16 - Nov 17

A cozy room with a fireplace, green sofas, a pool table, and a lamp.

5. Bromley View Inn

Bondville

Ski adventures await at this mountainside bed & breakfast, just steps from Green Mountain National Forest with premium slopes nearby.

CA $129 total

includes taxes & fees

Nov 22 - Nov 23

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

6. The Inn at Weathersfield

Perkinsville

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

CA $351 total

includes taxes & fees

Dec 1 - Dec 2

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

7. 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 $253 total

includes taxes & fees

Dec 6 - Dec 7

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

8. The Landgrove

Londonderry

CA $255 total

includes taxes & fees

Nov 16 - Nov 17

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

9. Castle Hill Resort And Spa

Cavendish

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

CA $232 total

includes taxes & fees

Nov 8 - Nov 9

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

10. The Hartness House

Springfield

CA $289 total

includes taxes & fees

Nov 8 - Nov 9

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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

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

Dave

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