Windsor vacation rentals

We found 135 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from vacation rentals in Windsor to find one that's perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, such as parking and air conditioning. At the end of the day, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Book a vacation rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a private vacation home. This city is well-known for its restaurants and shopping. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Windsor

Are you hoping to find things to do in the city? Venture out of your vacation home and experience everything that makes Windsor a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Berkshire East Ski Resort (11.5 mi / 18.5 km)
  • Jiminy Peak Mountain Resort (12.9 mi / 20.8 km)
  • Bousquet Ski Area (13.6 mi / 21.8 km)
  • Wyndhurst Golf & Club (16.1 mi / 25.9 km)
  • Waubeeka Golf Links (14.2 mi / 22.9 km)
  • Kennedy Park (14.8 mi / 23.8 km)

Exploring the natural landscape of Windsor

Whether you're an adventurous traveler or just want to take in the scenery, Windsor is a great place to spend some time outside. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Savoy Mountain State Forest (8.1 mi / 13.1 km)
  • Mount Greylock State Reservation Visitor Center (9.1 mi / 14.6 km)
  • Mohawk Trail State Forest (10.1 mi / 16.2 km)
  • Mount Greylock (10.8 mi / 17.4 km)
  • October Mountain State Forest (13.1 mi / 21.1 km)
  • Brodie Mountain (13.4 mi / 21.5 km)

Transportation to and around Windsor

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 13.8 mi (22.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away.

Frequently asked questions

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

A number of factors determine what you'll pay for your vacation rental in Windsor, such as the season, length of stay and type of property. But, all Vrbo homes have one thing in common — unbeatable value. Just enter your travel dates to find your home away from home.

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

The average price for a vacation rental near the beach in Windsor depends on when you're going and the type and size of property you're looking for. You can easily and quickly find prices on Vrbo by entering your travel dates and destination. Then use the handy filter tool to select the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a hot tub.

What are the top attractions for families in Windsor?

Keep your kids busy at these awesome family-friendly attractions in Windsor:

  • Tannery Falls
  • Mount Greylock State Reservation Visitor Center
  • Wahconah Falls State Park

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

Age restrictions can differ across properties on Vrbo, so be sure to check the rules of the vacation home in Windsor you're considering. But in general, it's 16, 18 or 21.

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

It all depends on the Windsor property. To view a list of options offering extended stays, simply enter your dates and number of people into the Vrbo search page. Look forward to having the entire place to yourself, along with the comforts of home like air conditioning, a kitchen and outdoor spaces to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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