Chester Vacation Rentals

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Vacation Rentals in Chester

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.

Kitchen

Washer

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock VT

Located in Woodstock, this vacation home is in a rural location, within a 10-minute drive of Union Arena Community Center and Five Elm Arches.

Kitchen

Washer

Shuttle or walk to village and lifts! Hot Tub + More!

Winhall VT

With a stay at this vacation home in Winhall, you'll be just steps from Green Mountain National Forest and 7 minutes by foot from Stratton Mountain Resort.

Hot Tub

Kitchen

Private Cabin 4BR 3BA, Fire pit, Pool table, BBQ Weber, Babbling Brook, Cornhole

Dover VT

With a stay at this vacation home in West Dover, you'll be a 2-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.

Kitchen

Washer

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish VT

With a stay at this vacation home in Cavendish, you'll be within a 15-minute drive of Okemo Mountain Resort and Phineas Gage Memorial.

Kitchen

Washer

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Woodstock VT

When you stay at this vacation home in Woodstock, you'll be on a river, within a 15-minute drive of Green Mountain National Forest and Quechee Gorge Bridge.

Kitchen

Washer

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

Plymouth VT

With a stay at this vacation home, you'll be centrally located in Plymouth, within a 10-minute drive of Amherst Lake and Echo Lake.

Hot Tub

Kitchen

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend VT

With a stay at this vacation home in Townshend, you'll be on the waterfront, within a 10-minute drive of Green Mountain National Forest and West River.

Pool

Kitchen

New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow VT

$529 nightly

$598 total

Oct 20 - Oct 21

Total with taxes and fees

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 Blue Lot.

Kitchen

Washer

Escape to Shadow Peak Retreat: Your Luxurious Vermont Getaway

manchester VT

Located in Manchester Center, this vacation home is within a 15-minute drive of Green Mountain National Forest and Bromley Mountain Ski Resort.

Kitchen

Washer

Charming VT ski retreat with hot tub, pool, fire pit & endless mountain views

Weston VT

With a stay at this vacation home in Weston, you'll be on a river, within a 10-minute drive of Green Mountain National Forest and West River.

Pool

Hot Tub

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT

With a stay at this vacation home in Jamaica (Pikes Falls), you'll be a 1-minute drive from Green Mountain National Forest and 9 minutes from Stratton Mountain Resort.

Kitchen

Washer

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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.