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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Chester chalets

Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is €356
includes taxes & fees
30 Jun - 1 Jul
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

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, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is €391
includes taxes & fees
14 Jul - 15 Jul
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Exterior

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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is €396
includes taxes & fees
29 Jun - 30 Jun
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Outdoor dining

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, (8 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 €465
includes taxes & fees
14 Jul - 15 Jul
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Outdoor spa tub

Mt Snow Game Room Chalet with Hot Tub

Mt Snow Game Room Chalet with Hot Tub
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Awesome stay!"
United States
Liz E.
The price is €722
includes taxes & fees
29 Jun - 30 Jun
Mt Snow Game Room Chalet with Hot Tub
Exterior

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC

Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
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 €729
includes taxes & fees
30 Jun - 1 Jul
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
Exterior

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Stratton
10.0 out of 10, Exceptional, (6 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
The price is €663
includes taxes & fees
28 Jun - 29 Jun
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Exterior

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 €882
includes taxes & fees
28 Jun - 29 Jun
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (3 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 €578
includes taxes & fees
26 Jun - 27 Jun
NEW Private Chalet - 4 mins to Mt Snow
Property grounds

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
Killington
9.0 out of 10, Wonderful, (6 reviews)
"Took a week long vacation with friends and this was the perfect place for us. A lot bigger than we had anticipated, equipped with every we needed and only a short 10 minute drive to Killington. The only issue we had was the wifi. We didn’t have any reception but luckily none of us needed to check in with work."
United States
Brigid P.
The price is €1,037
includes taxes & fees
26 Jun - 27 Jun
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
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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Top Chester Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."
Lauren 2-night trip
Posted 3 hours ago
Woodstock Inn & Resort

Find out more about Chester

Chester Chalets information

Number of reviews
13,777
Accommodation
104 Chalets
Lowest Price
€77
Highest Price
€200