Chester Vacation Rentals

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Vacation Rentals in Chester

Dog-friendly chalet cabin with valley view, deck, and private hot tub

With a stay at this vacation home in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.

Hot Tub

Kitchen

BruinsDen - Ski On Ski Off (Home Stretch Trail)

$1,208

includes taxes & fees

$1,083 per night

Dec 25 - Dec 26

When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 4-minute drive from Skye Peak Express Quad Ski Lift.

Hot Tub

Kitchen

5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!

With a stay at this vacation home in Jamaica, you'll be within a 10-minute drive of Stratton Mountain Resort and Green Mountain National Forest.

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

With a stay at this vacation home in Wardsboro, you'll be next to a golf course, within a 15-minute drive of Mount Snow and Green Mountain National Forest.

Pool

Hot Tub

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.

Pool

Hot Tub

4 Season Secluded Lakefront Home near Ski Mountains

Located in Mount Holly, this vacation home is on the waterfront, within a 15-minute drive of Lake Ninevah and Buttermilk Falls.

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

With a stay at this vacation home in West Dover, you'll be within a 15-minute walk of Mount Snow and Green Mountain National Forest.

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 3-minute drive from Sunrise Village Triple Ski Lift.

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.

Pool

Hot Tub

Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE

With a stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute drive of Okemo Mountain Resort and Red Lot.

Hot Tub

Kitchen

'Luna Stella' - West Dover Home 1 Mi. to Mt Snow!

With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and North Branch Deerfield River.

Log manor on 65 private acres of land with entertaining amenities & hot tub

This vacation home is 5.8 mi (9.3 km) from Woodstock Town Hall Theatre and 5.8 mi (9.4 km) from Red Wagon Toy Company.

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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.