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.

Where to stay around Windsor?

Our 2019 property listings offer a large selection of 43 vacation rentals near Windsor. From 27 Houses to 8 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Windsor for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Windsor?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Windsor:

  • East Hampton: 30 vacation rentals
  • Portland: 22 vacation rentals
  • Terryville: 52 vacation rentals
  • Amston: 25 vacation rentals
  • Mount Southington Ski Area: 114 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Windsor?

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

  • SS&C SummerWind Performing Arts Center: 97 vacation rentals
  • Windsor Historical Society: 90 vacation rentals
  • Oliver Ellsworth Homestead: 88 vacation rentals
  • Northwest Park: 83 vacation rentals
  • Vintage Radio and Communications Museum of Connecticut: 88 vacation rentals

But there are many other points of interest around Windsor listed on HomeAway 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. HomeAway has 27 Houses in Windsor. Our other popular types of vacation rentals in Windsor include:

  • Condos/Apartments: 8 rentals available
  • Cabins: 2 rentals available
  • Cottages: 2 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows 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.

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