Chester Vacation Rentals

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Vacation Rentals in Chester

Bright, Family-Friendly Lake View House Close to Okemo, Killington, Pico, Lakes

Plymouth VT

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

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.

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.

Birch Lodge - mountain views, hottub, minutes to Okemo!

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 Fletcher Farm School for the Arts and Crafts.

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

Winhall VT

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

Hot Tub

Kitchen

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.

SALE! MUSIC on the Mountain! Come enjoy this cozy, renovated home by Okemo Mtn!

Ludlow VT

With a stay at this vacation home in Ludlow, you'll be within a 15-minute drive of Okemo Mountain Resort and Fletcher Farm School for the Arts and Crafts.

Kitchen

Washer

Family Friendly Hilltop House In Putney Vermont

Putney VT

$268 nightly

$301 total

Sep 1 - Sep 2

Total with taxes and fees

Located in Putney, this vacation home is on a lake, within a 5-minute drive of Harlow's and Next Stage Arts.

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater VT

With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing Company.

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

Bridgewater VT

With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing Company.

As featured in the NY Times: charming, home on Lake Rescue, minutes from Okemo.

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 Lake Rescue.

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset VT

When you stay at this vacation home in Rupert, you'll be on a river, just steps from Green Mountain National Forest and a 4-minute drive from Dorset Historical Society Museum.

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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.