Where to stay around Chester, VT?

Our 2018 property listings offer a large selection of 538 vacation rentals near Chester. From 275 houses to 129 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Chester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chester:

  • Okemo Mountain Resort: 161 vacation rentals
  • Stratton Mountain Resort: 74 vacation rentals
  • Killington Ski Area: 245 vacation rentals
  • Stratton Mountain: 67 vacation rentals
  • West Woodstock: 19 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Chester?

VRBO offers a large selection of vacation rentals near lovely places in Chester. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Vermont Institute of Contemporary Arts: 828 vacation rentals
  • Bromley Mountain Ski Resort: 1,055 vacation rentals
  • Jackson Gore Ski Resort at Okemo: 1,165 vacation rentals
  • Tamarack Ski Lift: 902 vacation rentals
  • Long Trail Brewing Company: 1,196 vacation rentals

But there are many other points of interest around Chester listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent houses in Chester?

Yes, of course. VRBO has 275 houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Condos: 129 rentals available
  • Cabins: 29 rentals available
  • Chalets: 22 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including farmhouses and more.

Can I rent golf rental rentals in Chester?

Absolutely, VRBO has 392 golf rental rentals in Chester. You have also many other possibilities in Chester area, including:

  • Mountain view rentals: 248 rentals
  • Ski rentals: 191 rentals
  • Lake view rentals: 54 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Chester?

Yes, you can select your prefered vacation rental with online bookable among our 534 vacation rentals with online bookable available in Chester. Please use our search bar to access the selection of vacation rentals available.

    The cozy area of Chester awaits your stay

    The mountains and surrounding scenery provide a peaceful ambiance to your vacation home in Chester. Well known for its hiking, skiing and coffeehouses, this relaxing city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

    Activities and attractions in Chester

    Are you hoping to discover top things to see and do while you're in town? Venture out of your cozy vacation rental and experience everything that makes Chester a one-of-a-kind vacation spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

    • Okemo Mountain Resort (11.2 mi / 18 km)
    • Viking Nordic Center (9.8 mi / 15.7 km)
    • Magic Mountain Ski Resort (9.8 mi / 15.8 km)
    • Okemo Valley Golf Club (11.7 mi / 18.8 km)
    • Jackson Gore Ski Resort at Okemo (12.5 mi / 20.1 km)
    • Jamaica State Park (13.6 mi / 22 km)

    Seasonal weather in Chester

    Travelers enjoy Chester for its skiing. To make the most of the cold weather activities, you might consider visiting in December, March, February or January, when snowfall averages 23.26 inches and temperatures average 12°F.

    Exploring the natural features in Chester

    Whether you're an active traveler or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Chester. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

    • Grafton Ponds Outdoor Center (7 mi / 11.3 km)
    • Lowell Lake State Park (8.9 mi / 14.3 km)
    • Dorsey Park (10.5 mi / 16.8 km)
    • Ball Mountain State Park (12.9 mi / 20.8 km)
    • Buttermilk Falls (13.6 mi / 21.9 km)
    • Jamaica State Park (13.6 mi / 22 km)