Destination guide

Find the perfect holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city is well-known for its restaurants and shopping. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Activities and attractions in and around Windsor

Are you searching for things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Windsor has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bas Ridge Golf Course (6.2 mi / 10 km)
  • Hawley Bog Preserve (10.1 mi / 16.3 km)
  • Berkshire East Ski Resort (11.5 mi / 18.6 km)
  • Chesterfield Gorge (11.9 mi / 19.1 km)
  • Bousquet Ski Area (13.3 mi / 21.3 km)
  • Waubeeka Golf Links (13.9 mi / 22.3 km)
Natural features

Exploring the natural features in Windsor

Whether you're an outdoor enthusiast or just want to take in the scenery, Windsor is a great place to get out in nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Wahconah Falls State Park (3.7 mi / 6 km)
  • Savoy Mountain State Forest (7.8 mi / 12.6 km)
  • Mount Greylock State Reservation Visitor Center (8.8 mi / 14.2 km)
  • Mohawk Trail State Forest (9.9 mi / 15.9 km)
  • Hawley Bog Preserve (10.1 mi / 16.3 km)
  • Mount Greylock (10.4 mi / 16.8 km)
How to get there

Travelling to and around Windsor

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 13.8 mi (22.2 km) from the city centre. 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 29.2 mi (47.1 km) away.

Can I find a vacation rental around Windsor?

Yes, our 2020 property listings offer a large selection of 69 vacation rentals near Windsor. From 51 houses to 10 flats & 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 Vrbo.

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

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

  • Jiminy Peak Mountain Resort: 276 vacation rentals
  • Tanglewood Music Center: 437 vacation rentals
  • 62 Center for Theater and Dance: 177 vacation rentals
  • Charles H. Baldwin & Sons: 558 vacation rentals
  • Pleasant Valley Wilderness Sanctuary: 500 vacation rentals

But there are many other points of interest around Windsor listed on Vrbo UK 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 UK has 51 Houses in Windsor. Our other popular types of vacation rentals in Windsor include:

  • Flats: 10 rentals available
  • Cabins: 7 rentals available
  • Cottages: 7 rentals available

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

Can I find a vacation rental with pool in Windsor?

Yes, you can select your preferred vacation rental with pool among our 9 vacation rentals with pool available in Windsor. Please use our search bar to access the selection of vacation rentals available.