Chester Vacation Rentals

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Vacation Rentals in Chester

4 Season Secluded Lakefront Home near Ski Mountains

Mt Holly VT

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

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Ludlow VT

With a stay at this vacation home in Ludlow, you'll be in the mountains, within a 10-minute drive of Okemo Mountain Resort and Dorsey Park.

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub

Peru VT

With a stay at this vacation home in Peru (Bromley Mountain), you'll be within a 15-minute walk of Bromley Mountain Ski Resort and Green Mountain National Forest.

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow VT

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

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Plymouth VT

Located in Plymouth, this vacation home is in the mountains, within a 10-minute drive of Amherst Lake and Echo Lake.

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow VT

With a stay at this vacation home, you'll be centrally located in Ludlow, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the Arts and Crafts.

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT

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

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Bridgewater Corners VT

With a stay at this vacation home in Bridgewater Corners, you'll be on a lake, within a 5-minute drive of Killington Resort and Skyeship Express Gondola Stage I.

Ski in Ski out Condo! Pool access

Stratton VT

$507 nightly

$573 total

Dec 17 - Dec 18

Total with taxes and fees

When you stay at this vacation home in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National Forest.

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Ludlow VT

With a stay at this vacation home in Ludlow, you'll be on a lake, within a 10-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall VT

$1,077 nightly

$1,212 total

Dec 17 - Dec 18

Total with taxes and fees

With a stay at this vacation home 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

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT

Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.

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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.