Hotels in Windsor

Search for Windsor Hotels

  • Pay now or later on most rooms
  • Free cancellation on most rooms
  • Price Guarantee

Best Windsor Hotels

Windsor overview

Windsor is a friendly place, known for its jazz, and features 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. Make sure that you stop by Path of Life Garden and Paradise Park while you're here. Windsor is a family-friendly destination whilst 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 Hotels.com by checking our online maps. These display the areas and neighbourhoods 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 central 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

Outdoor 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 highlight 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. Favourite spots include:
  • • Paradise Park
  • • Mt Ascutney State Park
  • • Billings Park and Trail
  • • Quechee Gorge
  • • Mount Tom Peak
Popular places in the area include:
  • • Okemo Mountain Ski Resort
  • • Killington Resort

When to visit Windsor

Curious about when the best time to visit is? Here are the seasonal trends to help with your planning:

Seasonal temperatures
  • January-March: 10°C day, -13°C night
  • April-June: 27°C day, -2°C night
  • July-September: 28°C day, 6°C night
  • October-December: 19°C day, -12°C night
Seasonal average rainfall
  • January-March: 202 cm
  • April-June: 245 cm
  • July-September: 265 cm
  • October-December: 254 cm
  • Dining
  • Family-friendly