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Chester, Vermont, United States of America

Chester holiday rentals

We found 964 holiday rentals — enter your dates for availability

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Find spaces that suit your style

Houses

View 555 Houses

Cabins

View 65 Cabins

Condos/Apartments

View 301 Condos/Apartments

Cottages

View 65 Cottages

Chalets

View 31 Chalets

Bungalows

View 65 Bungalows

Farmhouses

View 25 Farmhouses

Townhouses

View 36 Townhouses

Studios

View 26 Studios

Hotels

View 52 Hotels
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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

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)
Weather

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 highlights

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 accommodation are available around Chester?

Our 2021 accommodation listings offer a large selection of 964 holiday rentals around Chester. From 555 holiday houses to 65 cabins, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Chester is on Stayz.

Can I rent Houses in Chester?

Yes, of course. Stayz offers 555 Houses in Chester. Our other popular types of Chester holiday rentals include:

  • Cabins: 65 holiday houses
  • Condos/Apartments: 301 holiday houses
  • Cottages: 65 holiday houses

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

Can I find a holiday accommodation with pool in Chester?

Yes, you can select your preferred holiday accommodation with pool among our 281 holiday homes with pool available in Chester. Please use our search bar to access the selection of holiday rentals available.