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Chester vacation rentals

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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
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
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

Stay near Chester's top sights

Photo of Country Girl Diner
Country Girl Diner29 locals recommend
Photo of MacLaomainn's Scottish Pub
MacLaomainn's Scottish Pub31 locals recommend
Photo of The Pizza Stone VT.
The Pizza Stone VT.27 locals recommend
Photo of Stone House Antique Center
Stone House Antique Center30 locals recommend
Photo of Southern Pie Cafe
Southern Pie Cafe18 locals recommend
Photo of the Free Range
the Free Range17 locals recommend

Other great vacation rentals in Chester

Tiny home in Chester
Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo
$229 per night
Private room in Chester
Whimsical Room & Private Bathroom in Historic Inn
$108 per night
Private room in Chester
Honeymoon Suite with Jacuzzi Tub in Historic Inn
$110 per night
Guest suite in Chester
Stone House Apartment- 2nd Floor
$152 per night
Rental unit in Chester
Beautiful 1BD Apartment w/ Mtn view
$138 per night
Rental unit in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
$156 per night
Guest suite in Chester
1868 Carriage House-Peaceful Getaway-Cozy+Quaint!
$171 per night
Rental unit in Chester
Vermont village apartment
$155 per night
Cottage in Chester
Quaint stone house!
$201 per night
Vacation home in Town of Rockingham
Cozy studio at Leslie's Tavern in Rockingham
$133 per night
Cabin in Chester
Candlelight Cabin
$182 per night
Guest suite in Chester
Adorable, Cozy 2 bedroom apartment walk to village
$129 per night
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  2. United States
  3. Vermont
  4. Windsor County
  5. Chester