Chester Vacation Rentals

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Vacation Rentals in Chester

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

Idyllic Lakefront House Suited Two Families

Ludlow VT

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

Kitchen

Washer

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT

With a stay at this vacation home in Jamaica (Pikes Falls), you'll be within a 15-minute drive of Stratton Mountain Resort and Solstice Ski Lift.

Kitchen

Washer

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

Dorset VT

When you stay at this vacation home in Dorset, you'll be on a river, just steps from Green Mountain National Forest and Emerald Lake State Park.

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

Ski Chalet with Hot Tub on Okemo Mountain

Ludlow VT

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 Blue Lot.

Hot Tub

Kitchen

LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views

Peru VT

Located in Peru, this vacation home is on the waterfront, within a 10-minute drive of Wild Wings Ski Touring Center and Taylor Farm.

Hot Tub

Kitchen

Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

Woodstock VT

With a stay at this vacation home in Woodstock (West Woodstock), you'll be within a 15-minute drive of Green Mountain National Forest and Union Arena Community Center.

Pool

Hot Tub

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

Ludlow VT

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

4 BR Mt Snow Okemo Ski Chalet w Amazing views!

Brattleboro VT

Located in Brattleboro, this vacation home is a 2-minute drive from Southern Vermont Natural History Museum and 6 minutes from Hogback Mountain Conservation Area.

Kitchen

Washer

Greystone 1830

Reading VT

When you stay at this vacation home in Reading, you'll be 11 minutes by car from Mt Ascutney State Park.

Washer

Dryer

Must-Visit Okemo Mountain Resort, 1 bedroom in a 3-bedroom house Springfield VT

Springfield VT

Located in Springfield, this vacation home is within a 5-minute drive of Muckross State Park and Eureka Schoolhouse.

Kitchen

Air conditioning

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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.