Discover a selection of 299 vacation rentals in Windsor, VT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including kitchens and WiFi. Prices start at $95 per night, and houses and cabins are popular options for a stay in Windsor. Either way, you'll find a rental for everyone's needs.
Destination guide

Travel to beautiful Windsor

The forests, mountains and countryside display a scene truly unique to Windsor. Travelers to this scenic city praise the golfing, hiking and bird watching. Okemo Mountain Resort and Killington Resort are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Sightseeing in and around Windsor

Are you searching for attractions to visit while you're in the area? Venture out of your vacation home and experience everything that makes Windsor a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Okemo Mountain Resort (15 mi / 24.2 km)
  • Killington Resort (19.5 mi / 31.4 km)
  • Union Arena Community Center (9.2 mi / 14.8 km)
  • Quechee State Park (9.8 mi / 15.7 km)
  • Vermont Institiute of Natural Science (10 mi / 16.2 km)
  • Quechee Ski Hill (10.9 mi / 17.5 km)
Natural features

Exploring the natural landscape of Windsor

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Windsor is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Path of Life Garden (2.6 mi / 4.2 km)
  • Mt Ascutney State Park (3.7 mi / 6 km)
  • Billings Park and Trail (9.3 mi / 14.9 km)
  • Quechee Gorge (9.8 mi / 15.7 km)
  • Quechee State Park (9.8 mi / 15.7 km)
  • Mount Tom Peak (9.9 mi / 15.9 km)
How to get there

How to get to and around Windsor

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 11.2 mi (18 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Springfield, VT (VSF-Hartness State), which is 11.4 mi (18.3 km) away.

If you'd prefer to travel by train, the main station serving the city is Windsor Station.

How many vacation rentals are available around Windsor, VT?

Our 2020 property listings offer a large selection of 299 vacation rentals around Windsor. From 179 house rentals to 25 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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

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

  • Mount Ascutney: 780 vacation rentals
  • Old Constitution House: 773 vacation rentals
  • Windsor Station: 774 vacation rentals
  • Path of Life Garden: 756 vacation rentals
  • The Sustainable Farmer: 767 vacation rentals

But there are many other points of interest around Windsor 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 Windsor?

Yes, of course. Vrbo has 179 Houses in Windsor. Our other popular types of vacation rentals in Windsor include:

  • Cabins: 25 rentals available
  • Condos/Apartments: 57 rentals available
  • Bungalows: 25 rentals available

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

Can I find a vacation rental with pool in Windsor?

Yes, you can select your preferred vacation rental with pool among our 108 vacation rentals with pool available in Windsor. Please use our search bar to access the selection of vacation rentals available.

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