Lodging Image

Search Chalets in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 NZ$766
includes taxes & fees
30 June - 1 July
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 NZ$784
includes taxes & fees
14 July - 15 July
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 NZ$792
includes taxes & fees
29 June - 30 June
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 NZ$917
includes taxes & fees
14 July - 15 July
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 NZ$1,396
includes taxes & fees
29 June - 30 June
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 NZ$1,400
includes taxes & fees
29 June - 30 June
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 NZ$1,303
includes taxes & fees
28 June - 29 June
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 NZ$1,705
includes taxes & fees
28 June - 29 June
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 NZ$1,153
includes taxes & fees
26 June - 27 June
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 NZ$2,025
includes taxes & fees
26 June - 27 June
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Out of the way location, so it was quite quiet. The pool was closed for some unknown reason. I stayed on the first floor and I could hear people walking on the floors above me, so if you consider yourself a light sleeper, this may not be the place for you unless you’re on an upper floor."
Kristen 1-night trip
Posted less than an hour ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Chalets information

Number of reviews
10,047
Accommodation
108 Chalets
Lowest Price
NZ$150
Highest Price
NZ$374

Explore a world of travel with Expedia