Windsor, Vermont holiday accommodation: short-term house rentals & properties

Discover a selection of 12 homes and other holiday rentals in Windsor that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find the best place to stay - Windsor

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Sleeps 10 · 4 bedrooms · 2 bathrooms

Find spaces that suit your style

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Condo/Apartment

Peace of mind
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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

The lush setting of Windsor is ready to explore

The forests, mountains and countryside are the perfect backdrop to your holiday home in Windsor. Travellers to this scenic city praise the golfing, hiking and bird watching. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Windsor

Are you hoping to find attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Windsor a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Quechee State Park (11 mi / 17.7 km)
Upper Valley Aquatic Center (11.4 mi / 18.3 km)
Quechee Ski Hill (12.7 mi / 20.5 km)
Whaleback Mountain (13 mi / 20.9 km)
Sugarbush Farm (13.4 mi / 21.5 km)
Saskadena Six Ski Area (15 mi / 24.1 km)

Exploring the natural features in Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Windsor. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

Mt Ascutney State Park (3.5 mi / 5.6 km)
Mount Ascutney (4.2 mi / 6.8 km)
Quechee Gorge Bridge (10.9 mi / 17.6 km)
Quechee State Park (11 mi / 17.7 km)
Marsh-Billings-Rockefeller National Historical Park (13.1 mi / 21.1 km)
Connecticut Lakes Region (13.4 mi / 21.5 km)

Travelling to and around Windsor

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.7 mi (17.3 km) from the city centre. 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 11.7 mi (18.8 km) away.

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

Frequently asked questions

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

Cabins are the most popular style of holiday home in Windsor, according to our data. Even if you have something different in mind, Stayz has properties in many sizes and shapes. Take a look at our options to find your perfect Windsor pad.

How much does it cost to rent a holiday home in Windsor?

Season, property type and length of stay are some factors that can determine the price of a holiday home. Simply add your travel dates to find your ideal fit. From cosy country cottages to sprawling villas, all Stayz holiday homes offer terrific value.

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

The average price for a holiday home by the beach in Windsor depends on when you're going and the type and size of property you're looking for. You can quickly and easily find prices on Stayz by entering your travel dates. Then use our handy filter tool to select the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.

What are popular home amenities in Windsor?

Some of the most popular home amenities people prefer in Windsor include tennis, a barbecue grill and a garden. Whether you're on the road with buddies, family or even pets, Stayz holiday properties include the best amenities for fun and relaxation with the people that matter most.

What are the top attractions for families in Windsor?

There's a ton of awesome things to do and see with the family in Windsor, including:

American Precision Museum
Maple Lanes
Mount Ascutney

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

It's advisable to check with the Windsor holiday property you're looking at on Stayz as age restrictions differ. However, it's generally 16, 18 or 21.

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

The length of time you can rent a holiday home in Windsor is down to the property. Simply enter your selected travel dates to look at a list of options offering extended stays. With tons of creature comforts such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get somewhere perfect to call your home away from home in Windsor.