A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check availability on Chester Ski Hotels

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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.
A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.
A variety of dishes including a steak, muffins, and a dessert with fruit.
A bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.

1. Fullerton Inn

Fullerton Inn
Chester Depot
CA $193
CA $211 total
includes taxes & fees
Sep 1 - Sep 2
Fullerton Inn

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

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
CA $389
CA $899 total
includes taxes & fees
Aug 31 - Sep 1
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A spacious lobby with a fireplace, leather seating, and a chandelier.
An indoor swimming pool with four chairs and a hot tub.

3. Pointe at Castle Hill Resort

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 $132
CA $151 total
includes taxes & fees
Sep 2 - Sep 3
Pointe at Castle Hill Resort
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.
A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.
A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.

4. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
CA $249
CA $274 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Springfield Hotel
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.
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".
A hotel room with a large bathtub, a bed with a colorful quilt, two bedside lamps, and a framed picture on the wall.

5. The Upper Pass Lodge at Magic Mountain

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 $116
CA $129 total
includes taxes & fees
Sep 29 - Sep 30
The Upper Pass Lodge at Magic Mountain
A cozy room with a fireplace, green sofas, a pool table, and a lamp.
A bedroom with a wooden floor, a bed with a white bedspread, a nightstand with a lamp, a dresser, and a television on the dresser.
A wooden interior with a dining table set for four, a wooden cabinet with glass doors, and a kitchen area with a refrigerator and cabinets.
A deck with white railings overlooking a forested area and a mountain in the distance.

6. Bromley View Inn

Bromley View Inn
Bondville
  • Ski adventures await at this mountainside bed & breakfast, just steps from Green Mountain National Forest with premium slopes nearby.
CA $106
CA $117 total
includes taxes & fees
Aug 31 - Sep 1
Bromley View Inn
A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.
A stone facade with a wooden door, steps leading up to a porch, and a small white chair outside.
A room with a red sofa, armchairs, a coffee table, and a fireplace. There is a window with a view of trees and a chandelier.
A restaurant with a stone wall bar area, wooden tables, and chairs.

7. The Hartness House

The Hartness House
Springfield
CA $246
CA $271 total
includes taxes & fees
Aug 31 - Sep 1
The Hartness House
A red house with a covered porch and a chimney.
A living room with a wood-burning stove, a blue armchair, and a bookshelf.
A kitchen with white cabinets, a microwave, a stove, and a sink.
Two single beds with wooden frames and striped bedding, a small wooden nightstand with a lamp, and a window with a view of greenery.

8. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
CA $236
CA $511 total
includes taxes & fees
Aug 31 - Sep 1
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.
A cozy room with a large bed, a fireplace, and a brick wall.
A wooden interior with a pool, benches, and a clock.
A banquet hall with multiple round tables set for dining, featuring chandeliers and brick walls.

9. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
CA $186
CA $202 total
includes taxes & fees
Sep 7 - Sep 8
The Common Man Inn & Restaurant
A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.
A lobby with a leather sofa, a television mounted on the wall, a painting, and a security control panel.
A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.
A stone wall surrounding a swimming pool with a metal handrail.

10. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
  • Discover slope-side luxury at this Stratton Mountain Resort with a free ski shuttle, hot tub, and sauna for perfect winter getaways.
CA $169
CA $204 total
includes taxes & fees
Sep 6 - Sep 7
The Black Bear Lodge at Stratton Mountain Resort
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Choose what matters most at ski hotels in Chester

Resort
4 stars
5 stars
Spa
Family-friendly

Top Chester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Room was clean and staff was excellent. Breakfast was good and plentiful."
David 2-night trip
Posted less than an hour ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice room and property. With was down."
Amanda 1-night trip
Posted 20 hours ago
The Palmer House Resort, an Ascend Collection Hotel
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."
Maryalice 2-night trip
Posted 21 hours ago
The Equinox Golf Resort And Spa
On The River Inn

On The River Inn

10/10 Excellent
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."
Christopher 4-night trip
Posted 1 day ago
On The River Inn
Bromley View Inn

Bromley View Inn

10/10 Excellent
"Beautiful cozy inn surrounded by trees and mountains. An incredible view with a cabin setting. Check-in was simple with coffee available 24/7"
Marvin 1-night trip
Posted 3 days ago
Bromley View Inn
The Shire Woodstock

The Shire Woodstock

8/10 Good
"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."
Ann 3-night trip
Posted 3 days ago
The Shire Woodstock
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Very clean. Good full breakfast."
Barbara 1-night trip
Posted 4 days ago
Hampton Inn Brattleboro
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 4 days ago
Best Western Plus Keene Hotel
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 7 days ago
Colonial Motel

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