Discover a selection of 45 vacation rentals in Windsor, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $64 per night, and houses and condos are popular options for a stay in Windsor. Either way, you'll find a rental for everyone's needs.
Destination guide

Why people love visiting friendly Windsor

Learn about the unique charm of Windsor with a stay in a private vacation home. This city is welcoming and romantic, recognized for its restaurants, shopping and theme park. Springfield Armory and Mark Twain House are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.


Sightseeing in and around Windsor

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

  • Wintonbury Hills Golf Course (4.5 mi / 7.2 km)
  • Keney Park (4.6 mi / 7.4 km)
  • Gillette Ridge Golf Course (5.4 mi / 8.7 km)
  • Talcott Mountain State Park (6.3 mi / 10.1 km)
  • Wampanoag Country Club (6.5 mi / 10.5 km)
  • East Hartford Golf Course (7 mi / 11.2 km)
Natural features

Exploring the natural landscape of Windsor

Whether you're an adventurous traveler or just want to appreciate the scenery, Windsor is a great place to get out in nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Bushnell Park (7.4 mi / 11.9 km)
  • Northwest Park (2.2 mi / 3.5 km)
  • Wintonbury Hills Playground (3.1 mi / 4.9 km)
  • Keney Park (4.6 mi / 7.4 km)
  • Penwood State Park (5.5 mi / 8.8 km)
  • Penwood State Park (6.2 mi / 10 km)
How to get there

Transportation to and around Windsor

The nearest airport is in Hartford, CT (BDL-Bradley Intl.), located 4.1 mi (6.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Hartford, CT (HFD-Hartford - Brainard), which is 9 mi (14.4 km) away.

If you're traveling by train, you can make your way to Windsor Station.

How many vacation rentals are available around Windsor, CT?

Our 2020 property listings offer a large selection of 45 vacation rentals around Windsor. From 25 house rentals to 11 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Windsor?

Vrbo offers a large selection of vacation rentals near lovely places in Windsor. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Windsor Arts Center: 84 vacation rentals
  • Windsor Historical Society: 81 vacation rentals
  • SS&C SummerWind Performing Arts Center: 87 vacation rentals
  • Northwest Park: 77 vacation rentals
  • Oliver Ellsworth Homestead: 79 vacation rentals

But there are many other points of interest around Windsor listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Windsor?

Yes, of course. Vrbo has 25 Houses in Windsor. Our other popular types of vacation rentals in Windsor include:

  • Condos/Apartments: 11 rentals available
  • Studios: 10 rentals available
  • Hotels: 2 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Guest houses and more.

Can I find a vacation rental with pool in Windsor?

Yes, you can select your preferred vacation rental with pool among our 4 vacation rentals with pool available in Windsor. Please use our search bar to access the selection of vacation rentals available.