Windsor County holiday lettings

We found 2,371 holiday rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
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Select from 620 houses, 65 apartments and other holiday rentals to find the perfect place for your stay in Windsor County. Whether you're going on holiday with family or friends, holiday homes have the amenities that you expect for your stay, which might include a garden and pool. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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Choose a holiday rental for your Windsor County getaway

Learn about the unique charm of Windsor County with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Windsor County

Are you searching for top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Windsor County a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sugarbush Farm (3.8 mi / 6.1 km)
  • Quechee State Park (5.5 mi / 8.9 km)
  • Upper Valley Aquatic Center (8.8 mi / 14.2 km)
  • Killington Golf Course (13.7 mi / 22.1 km)
  • Killington Resort (13.9 mi / 22.3 km)
  • Killington Adventure Center (13.9 mi / 22.4 km)

Exploring the natural landscape of Windsor County

Whether you're an active traveller or just want to spend some time taking in the scenery, Windsor County is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Marsh-Billings-Rockefeller National Historical Park (1.2 mi / 2 km)
  • Quechee State Park (5.5 mi / 8.9 km)
  • Quechee Gorge Bridge (5.6 mi / 9 km)
  • Mount Ascutney (12.9 mi / 20.8 km)
  • Mt Ascutney State Park (13 mi / 20.9 km)
  • Gifford Woods State Park (14.9 mi / 24 km)

Transport options to and around Windsor County

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 19.5 mi (31.3 km) from the city centre.

If you'd rather travel by train, make your way to White River Junction Station or Windsor Station to see more of the city.

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