Hotels in Windsor, Vermont

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Windsor overview

Windsor is a friendly locale known for its jazz, and surrounded by picturesque views of the jungle and mountains. You'll enjoy the ample beer and chocolate options, along with outdoor areas for hiking and walking. This winter paradise is home to popular ski areas such as Okemo Mountain Ski Resort and Killington Resort. Be sure stop by Path of Life Garden and Paradise Park while you're here. Windsor is a family-friendly destination while offering something for everyone.

Where to stay in Windsor

Whether you're planning to stay for a night or for the week, the area around Windsor has accommodations to fit every need. Search for hotels in Windsor with by checking our online map. Our maps display the areas and neighborhoods around all Windsor hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Windsor hotel deals are here with our lowest price guarantee.

How to get to Windsor

Fly in to Lebanon, NH (LEB-Lebanon Municipal), 11.2 mi (18 km) from downtown Windsor. Rutland, VT (RUT-Rutland Southern Vermont Regional) is the next closest major airport, 24.9 mi (40.1 km) away. Windsor Station is the closest train station.

What to see around Windsor

Outdoorsy fun is on hand like golf and sledding, along with attractions such as:
  • • Brownsville Trail
  • • Quechee State Park
  • • Quechee Ski Hill
  • • Arrowhead Recreation Area
  • • Suicide Six Ski Area
A top draw is the area's jazz scene, as well as places like:
  • • Cornish Colony Museum
  • • American Precision Museum
  • • Woodstock Town Hall Theatre
  • • Dana House Museum
  • • Billings Farm and Museum
Its forests, jungle, and mountain views offer a glimpse of the natural beauty and favorite spots include:
  • • Paradise Park
  • • Mt Ascutney State Park
  • • Billings Park and Trail
  • • Quechee Gorge
  • • Mount Tom Peak
Some popular places in the area include:
  • • Okemo Mountain Ski Resort
  • • Killington Resort

When to visit Windsor

Curious about when's the best time to visit? Here are the seasonal norms to help with your planning:

Seasonal temperature averages
  • January-March: 50°F day, 8°F night
  • April-June: 81°F day, 28°F night
  • July-September: 83°F day, 42°F night
  • October-December: 66°F day, 11°F night
Seasonal rainfall averages
  • January-March: 7.95 inches
  • April-June: 9.65 inches
  • July-September: 10.43 inches
  • October-December: 10.00 inches