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.

How many holiday rentals are available around Windsor?

Our 2019 accommodation listings offer a large selection of 57 holiday lettings around Windsor. From 33 Houses to 10 Flats, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Windsor?

HomeAway offers a large selection of holiday accommodations near great places in Windsor. From HomeAway travellers, the most popular points of interest to stay near are:

  • Jiminy Peak Mountain Resort: 250 holiday lettings
  • Tanglewood Music Center: 392 holiday lettings
  • 62 Center for Theater and Dance: 185 holiday lettings
  • Pleasant Valley Wilderness Sanctuary: 446 holiday lettings
  • Williams College Museum of Art: 198 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Houses in Windsor?

Yes, of course. HomeAway offers 33 Houses in Windsor. Our other popular types of Windsor holiday rentals include:

  • Flats: 10 self catering accommodations
  • Cabins: 7 self catering accommodations
  • Cottages: 7 self catering accommodations

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

Can I find a holiday accommodation with pool in Windsor?

Yes, you can select your preferred holiday accommodation with pool among our 8 holiday homes with pool available in Windsor. Please use our search bar to access the selection of holiday rentals available.

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