Destination guide

The cosy area of Chester awaits your stay

The mountains and surrounding scenery provide a peaceful ambience to your holiday home in Chester. Well known for its hiking, skiing and coffee shops, 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 cosy holiday rental and experience everything that makes Chester a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers 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 59.08 inches and temperatures average -11°F.

Natural features

Exploring the natural features in Chester

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

  • 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)
How to get there

Transport options to and around Chester

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.2 mi (40.6 km) away.

How many holiday rentals are available around Chester?

Our 2020 accommodation listings offer a large selection of 1,051 holiday lettings around Chester. From 344 flats & apartments to 462 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chester:

  • Quechee: 99 holiday homes
  • West Dover: 562 holiday homes
  • Bondville: 202 holiday homes
  • Bridgewater Corners: 23 holiday homes
  • Forest Farms: 18 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Chester? offers a large selection of holiday accommodations near great places in Chester. From travellers, the most popular points of interest to stay near are:

  • Bonnie's Bundles Dolls: 890 holiday lettings
  • DaVallia Art & Accents: 903 holiday lettings
  • Skyeship Express Stage I: 1,179 holiday lettings
  • Baltimore Covered Bridge: 598 holiday lettings
  • Claremont Opera House: 433 holiday lettings

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

Can I rent Flats in Chester?

Yes, of course. offers 344 Flats in Chester. Our other popular types of Chester holiday rentals include:

  • Houses: 462 self catering accommodations
  • Cottages: 58 self catering accommodations
  • Cabins: 58 self catering accommodations

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

Can I find a holiday accommodation with pool in Chester?

Yes, you can select your preferred holiday accommodation with pool among our 318 holiday homes with pool available in Chester. Please use our search bar to access the selection of holiday rentals available.