Windsor, MA, USA

Windsor, MA, USA

We found 124 vacation rentals — enter your dates for availability


Find the best place to stay — Windsor

Where to stay around Windsor?

Our 2018 property listings offer a large selection of 124 vacation rentals near Windsor. From 42 houses to 40 condos, 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 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:

  • Jiminy Peak Mountain Resort: 416 vacation rentals
  • Western Gateway Heritage State Park: 295 vacation rentals
  • Tanglewood Music Center: 680 vacation rentals
  • Berkshire East Ski Resort: 213 vacation rentals
  • 62 Center for Theater and Dance: 206 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 42 houses in Windsor. Our other popular types of vacation rentals in Windsor include:

  • Condos: 40 rentals available
  • Apartments: 9 rentals available
  • Cabins: 5 rentals available

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

Can I rent skiing rentals in Windsor?

Absolutely, HomeAway has 82 skiing rentals in Windsor. You have also many other possibilities in Windsor area, including:

  • Golf rentals: 76 rentals
  • Mountain rentals: 63 rentals
  • Lake rentals: 17 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Windsor?

Yes, you can select your preferred vacation rental with pool among our 50 vacation rentals with pool available in Windsor. Please use our search bar to access the selection of vacation rentals available.