Where to stay around Windsor, MA?

Our 2018 property listings offer a large selection of 164 vacation rentals near Windsor. From 83 Condos/Apartments to 47 Houses, 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 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:

  • Jiminy Peak Mountain Resort: 419 vacation rentals
  • Bissell Covered Bridge: 237 vacation rentals
  • Berkshire East Ski Resort: 232 vacation rentals
  • Pittsfield Station: 574 vacation rentals
  • Mount Greylock: 255 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 Condos/Apartments in Windsor?

Yes, of course. VRBO has 83 Condos/Apartments in Windsor. Our other popular types of vacation rentals in Windsor include:

  • Houses: 47 rentals available
  • Studios: 12 rentals available
  • Bungalows: 10 rentals available

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

Can I find a vacation rental with pool in Windsor?

Yes, you can select your prefered vacation rental with pool among our 80 vacation rentals with pool available in Windsor. Please use our search bar to access the selection of vacation rentals available.

    Find the perfect vacation rental for your Windsor getaway

    Learn about the unique charm of Windsor with a stay in a private vacation home. This city is well-known for its restaurants and shopping. A vacation 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 vacation 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 center:

    • 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)

    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 center:

    • 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)