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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chester chalets

A two-story wooden house with a porch, surrounded by snow-covered trees.

1. Mountain Chalet, sleeps 8, with hot tub

Mountain Chalet, sleeps 8, with hot tub
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
The price is NZ$1,266
includes taxes & fees
2 Dec - 3 Dec
Mountain Chalet, sleeps 8, with hot tub
A wooden house with a porch lit by string lights, surrounded by snow.

2. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
The price is NZ$663
includes taxes & fees
11 Nov - 12 Nov
Chalet Mount Snow/Stratton Skiing/hiking
A white, single-story cabin with a red door, surrounded by trees.

3. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "
United States
fran g.
The price is NZ$1,827
includes taxes & fees
11 Nov - 12 Nov
Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

4. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is NZ$787
includes taxes & fees
23 Nov - 24 Nov
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A wooden cabin with a front porch, surrounded by a forest.

5. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (14 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is NZ$834
includes taxes & fees
16 Nov - 17 Nov
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A small, single-story house with a front porch, a red door, and a white fence.

6. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
Wardsboro
9.6 out of 10, Exceptional, (4 reviews)
"Everything was wonderful and perfect for our family. Super clean and great Vermont experience"
United States
Lisa B.
The price is NZ$808
includes taxes & fees
16 Nov - 17 Nov
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

7. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is NZ$839
includes taxes & fees
16 Nov - 17 Nov
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A two-story cabin with a deck, large windows, and a hot tub.

8. Chalet 1mi to Mount Snow with cinema and hot tub

Chalet 1mi to Mount Snow with cinema and hot tub
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Awesome stay!"
United States
Liz E.
The price is NZ$1,375
includes taxes & fees
15 Nov - 16 Nov
Chalet 1mi to Mount Snow with cinema and hot tub
A spacious living room with a fireplace, blue sofas, a leather armchair, and a ceiling fan.

9. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
Stratton
10.0 out of 10, Exceptional, (7 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
The price is NZ$1,262
includes taxes & fees
11 Nov - 12 Nov
Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna
A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

10. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
The price is NZ$920
includes taxes & fees
22 Nov - 23 Nov
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

11. NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great place close enough to everything you need but set off the road for quiet evenings. Clean, spacious open floor plan great accommodation that checks all the needs for a ski getaway. "
United States
Mark C.
The price is NZ$1,114
includes taxes & fees
16 Nov - 17 Nov
NEW Private Chalet - 4 mins to Mt Snow
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.
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Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top reviews in Chester

A large stone building with a steep roof, surrounded by dense forest and hills.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish

10/10 Excellent

Fully met our expectations. Spacious condo, quality fit out, quiet and a high quality restaurant on site in a beautiful building.
Australia
peter
Reviewed June 29, 2016
Castle Hill Resort And Spa