Windsor County vacation rentals

We found 2,411 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 640 houses, 63 apartments, and other vacation rentals to find the perfect place for your stay in Windsor County. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you need and want for your stay, which might include cable TV and a washer and dryer. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.

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Choose a vacation rental for your Windsor County getaway

Learn about the unique charm of Windsor County with a stay in a private vacation home. This city has something for everyone. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation 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 looking for top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Windsor County a one-of-a-kind vacation spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Saskadena Six Ski Area (3 mi / 4.8 km)
  • 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)

Exploring the natural landscape of Windsor County

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windsor County is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Lake Rescue (15.1 mi / 24.3 km)

Transportation 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 center.

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

Frequently asked questions

What is the best area to stay in Windsor County when booking a vacation rental?

If your itinerary includes Windsor County, Ludlow is regarded as one of the most popular locations to spend a vacation. While here, explore wonderful sights like Okemo Mountain Resort and Lake Rescue.

What is the most popular type of vacation rental accommodation in Windsor County?

Houses are the most popular type of vacation rental in Windsor County, according to our data. Even if you have a different idea in mind, Vrbo has vacation homes in many sizes and shapes. Look through our options to find your perfect Windsor County pad.

How much does it cost to rent a vacation rental in Windsor County?

The average price for a vacation home in Windsor County is determined by several factors, like season, property type and length of stay. Whether you're searching for a sprawling villa with a pool or a quaint cottage just enough for two, just enter your dates of travel to view some great-value stays.

How much does it cost to rent a beach house in Windsor County?

The average price for a vacation home by the beach in Windsor County will depend on when you'll be there and the size and type of property you want. Find prices quickly and easily on Vrbo by entering your travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.

What are popular rental amenities in Windsor County?

Off-street parking options, a microwave oven and a fridge head the list of most popular rental amenities in Windsor County. Whether you plan to travel as a party of one, with a partner or a group of friends, Vrbo can help you find a vacation home that matches your tastes with all the features you need.

Are there large group vacation rentals in Windsor County?

Choose from 240 vacation homes in Windsor County that can sleep 10 or more people. Whether you're planning a get-together with extended family or an event like a party, there's enough space to get your group together under one roof.

What are the top attractions for families in Windsor County?

Keeping the kids entertained during your stay in Windsor County is simple with these leading family-friendly attractions:

  • Saskadena Six Ski Area
  • Upper Valley Aquatic Center
  • Billings Farm and Museum

Can I find two-bedroom vacation rentals in Windsor County?

You can select from 157 two-bedroom vacation rentals in Windsor County. Put the kids in the second room or fill it with a couple of your best buddies. There's a comfy spot for whoever's fortunate enough to be joining your journey.

Are there vacation rentals with WiFi in Windsor County?

Whether you'd like to stay in touch with the news, reply to emails or surf social media, there are 256 vacation homes with WiFi in Windsor County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

How old do you have to be to rent a vacation rental in Windsor County?

The minimum required age is usually 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your preferred Windsor County vacation rental before booking your stay.

How long can I rent a vacation rental in Windsor County for?

The amount of time you can book a Windsor County vacation rental for differs depending on the property. Just tap in your preferred travel dates to view available options offering extended stays. They feature all you require to make your extended trip more convenient and comfortable, like kitchens and air conditioning. Some Vrbo vacation rentals may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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