Photo by William E Berry Jr.

Windsor vacation rentals

We found 256 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 12 homes and other vacation rentals in Windsor that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you expect for your stay, including WiFi and parking. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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The lush setting of Windsor is ready to explore

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

Activities and attractions in Windsor

Do you want to find attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to 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:

  • 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 an active traveler or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Windsor. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Windsor

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.7 mi (17.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away.

If you're traveling by train, the main station is Windsor Station.

Frequently asked questions

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

Cabins are the most popular style of vacation rental in Windsor, according to our data. Even if you have something different in mind, Vrbo 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 vacation rental in Windsor?

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

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

The average price for a vacation rental 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 Vrbo 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 rental amenities in Windsor?

Some of the most popular rental 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, Vrbo vacation 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 vacation rental in Windsor?

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

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

The length of time you can rent a vacation rental 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.

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