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Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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

The Stone Schoolhouse
SUPERHOST
Entire cottage · 3 guests · 2 beds · 1 bath

The Stone SchoolhouseThe Stone Schoolhouse is in an amazing location - 100 yards from the historic Bartonsville Covered bridge -Five minutes from I 91 exit 6 -Five minutes from Chester VT -Two miles from The Vermont Country Store -Located in the heart of Southern Vermont skiing, hiking and biking The light airy 1840 house itself is charming, filled with art, books and enticing artifacts. The property includes a lovely woodland screened chalet. You will have the entire house to yourself.

Inviting studio apartment above barn in Vermont
SUPERHOST
Barn · 4 guests · 2 beds · 1 bath

Inviting studio apartment above barn in VermontThis 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.

Green Mountain Guest Suite
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Green Mountain Guest SuiteEnjoy the beauty of Vermont in this private guest suite on 10 stunning acres at the foot of the Green Mountains. You'll be walking distance to Chester's Village Green and only minutes to Ludlow and Okemo Mountain Resort. Panoramic mountain views, wildflower meadows, private access to the Williams River, nature trails, and three private ponds are yours to explore. Need to store your ski gear? No problem! The barn has plenty of space. Friendly dogs are welcome!

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Popular amenities for Chester vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Chester

  1. Entire chalet
  2. Chester
Spacious Chalet near Golf, Breweries & Live Music
SUPERHOST
  1. Entire rental unit
  2. Chester
Beautiful 2 Bedrooms in Mountains w/ full kitchen
SUPERHOST
  1. Entire guest suite
  2. Cavendish
Historic Jenny House Guest Suite
SUPERHOST
  1. Entire rental unit
  2. Andover
Private Hilltop farm apartment
SUPERHOST
  1. Entire rental unit
  2. Ludlow
Okemo Vermont Getaway
SUPERHOST
  1. Private room
  2. Chester
Stone House Bed & Breakfast - Clark Room
SUPERHOST
  1. Entire residential home
  2. Ludlow
Okemo Mtn. 4-Seasons destination! Come visit soon!
  1. Entire residential home
  2. Chester
Charm Near the Heart of Chester
SUPERHOST
  1. Entire residential home
  2. Grafton
Modern Grafton Artist Retreat Near Skiing
SUPERHOST
  1. Entire rental unit
  2. Chester
Beautiful 1BD Apartment w/ Mtn view
SUPERHOST
  1. Private room
  2. Baltimore
Wake up to Mountain views in a Vermont studio Apt.
  1. Farm stay
  2. Baltimore
Hawk Mtn Farm's lovely one bedroom apartment!

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