Windsor County holiday rentals

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Select from 619 houses, 66 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.

Popular Windsor County destinations on Stayz

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Find the best place to stay - Windsor County

View of the house from the driveway. On over an acre, surrounded by trees.

"The Crooked House" with A/C and sauna on private wooded lot near Killington

Sleeps 8 · 3 bedrooms · 2+ bathrooms

living room with fireplace and gorgeous custom details

Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W/Jacuzzi&Swim Pond&CentralAC!

Sleeps 28 · 7 bedrooms · 3+ bathrooms

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Sleeps 8 · 3 bedrooms · 2 bathrooms

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:

Saskadena Six Ski Area (3 mi / 4.8 km)
Sugarbush Farm (3.8 mi / 6.1 km)
Quechee Ski Hill (4.4 mi / 7 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)

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)
Ottaquechee River (2.2 mi / 3.6 km)
Quechee Gorge Bridge (5.6 mi / 9 km)
Lakota Lake (7.7 mi / 12.3 km)
Silver Lake State Park (8.8 mi / 14.2 km)
Mount Ascutney (12.9 mi / 20.8 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.

Frequently asked questions

What is the best area to stay in Windsor County when booking a holiday home?

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

What is the most popular type of holiday home accommodation in Windsor County?

Houses are the most popular type of holiday home in Windsor County, according to our data. Even if you have a different idea in mind, Stayz has holiday 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 holiday home in Windsor County?

The average price for a holiday 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 holiday 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 Stayz 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 home amenities in Windsor County?

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

Are there large group holiday homes in Windsor County?

Choose from 240 holiday 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 Centre
Billings Farm and Museum

Can I find two-bedroom holiday homes in Windsor County?

You can select from 157 two-bedroom holiday homes 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 holiday homes 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 holiday homes with WiFi in Windsor County. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.

How old do you have to be to rent a holiday home in Windsor County?

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

How long can I rent a holiday home in Windsor County for?

The amount of time you can book a Windsor County holiday home 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 Stayz holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.