Chester vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Private room in Chester

Bohemian Guest Suite

Travel for work or pleasure, you'll love staying with us in our bohemian inspired suite. Chester, is a small but quaint town with many cute boutiques to visit. If you're an outdoor enthusiast, you'll love the abundance of hiking trails, rivers and streams to explore. Okemo, Bromley and Stratton Mountain Ski Resorts are all within 30 minutes. One queen bed and two twin mattresses in separate closets/cubby & pack-n-play available upon request. Snow tires and 4wheel drive recommended in winter.

$90 per night

SUPERHOST

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

$90 per night

SUPERHOST

Private room in Chester

Bright and cheery!

Bright and cheery, the Summer room is an ode to the long warm days of Summer in Vermont. Located just off the Green in Chester, VT with a plethora of things to do in the area. From skiing and boarding at one of the 5 nearby skiing areas, to shopping the charming village of Chester, you're sure to have a relaxing and memorable visit.

$120 per night

SUPERHOST