Chester Chalets
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Chalets in Chester
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Plymouth VT
Located in Plymouth, this chalet is in the mountains, within a 5-minute drive of Calvin Coolidge Historic Site and Calvin Coolidge Homestead.
Kitchen
Washer
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Ludlow VT
With a stay at this chalet in Ludlow, you'll be within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the Arts and Crafts.
Kitchen
Washer
Green Mountain Manor - Ski and Summer Chalet
Winhall VT
With a stay at this chalet in Winhall, you'll be next to a golf course, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
Pool
Hot Tub
Cozy Creekside Chalet centrally located near 4 ski resorts
Weston VT
Located in Weston, this chalet is in the mountains, within a 5-minute drive of West River and Mill Museum.
Kitchen
Washer
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Winhall VT
With a stay at this chalet in Winhall, you'll be in the mountains, within a 10-minute drive of Bromley Mountain Ski Resort and Green Mountain National Forest.
Hot Tub
Kitchen
Private 6 bedroom Chalet 5min to Mt Snow
Dover VT
With a stay at this chalet in West Dover, you'll be next to a golf course, within a 10-minute drive of Mount Snow and Green Mountain National Forest.
Kitchen
Washer
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Winhall VT
When you stay at this chalet in Winhall, you'll be in the mountains, within a 15-minute walk of Stratton Mountain Resort and Green Mountain National Forest.
Pool
Hot Tub
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
Mount Holly VT
A stay at this chalet places you in the heart of Belmont, within a 5-minute drive of Green Mountain National Forest and Star Lake.
Kitchen
Washer
Cozy chalet w/ hot tub & fire pit
Stratton Mountain VT
When you stay at this chalet in Stratton, you'll be on a lake, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National Forest.
Pool
Hot Tub
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Ludlow VT
With a stay at this chalet in Ludlow, you'll be in the mountains, within a 5-minute drive of Okemo Mountain Resort and Sunshine Ski Lift.
Hot Tub
Kitchen
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro VT
$703 nightly
The price is $794 total per night
$794 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
With a stay at this chalet in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Kitchen
Washer
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.
Chester Chalets essential information
Accommodation | 112 Chalets |
|---|---|
Lowest Price | $794 |
Highest Price | $794 |
Popular accommodation | Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt. , Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails, Green Mountain Manor - Ski and Summer Chalet, Cozy Creekside Chalet centrally located near 4 ski resorts, Beautiful Manchester VT Mountain Retreat w/Hot Tub, Private 6 bedroom Chalet 5min to Mt Snow, Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!, Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni, Cozy chalet w/ hot tub & fire pit, Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!, Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!, Cozy 4bd - Ski Okemo, Killington, Magic & Bromley |
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