Hotels in Winchester, Massachusetts

Search & Compare Winchester Hotels

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

Best hotels in Winchester

Winchester overview

Surrounded by picturesque views of mountains and flowers, Winchester is known for its natural features and sports. Sports fans will enjoy soccer. Those seeking the perfect souvenir may want to head over to Faneuil Hall Marketplace and Copley Place to shop. Harvard Square and USS Constitution Museum are popular places to visit. Winchester is a family- and business-friendly destination with something for everyone.

Where to stay in Winchester

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

How to get to Winchester

Fly in to Boston, MA (BOS-Logan Intl.), 8.9 mi (14.3 km) from downtown Winchester.

Train stations include:
  • • Winchester Station
  • • Winchester Wedgemere Station

What to see around Winchester

Fun activities in the area include these attractions:
  • • Burlington Ice Palace
  • • Sky Zone
  • • Agganis Arena
  • • Boston Paintball
  • • TD Garden
Known for its family-friendly sights such as:
  • • Artisans Asylum
  • • New England Aquarium
  • • Franklin Park Zoo
  • • CoCo Key Water Resort - Boston
  • • Andover Bird Sanctuary
Its lakes, mountain views, and wildlife are notable, and top spots for nature lovers include:
  • • Mystic River Reservation
  • • Royall Park
  • • Logan Park
  • • Magoun Park
  • • Prospect Hill Park
Some popular places in the area to visit include:
  • • Harvard Square
  • • USS Constitution Museum
  • • Boston University
  • • Fenway Park
  • • Boston Public Garden

When to visit Winchester

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

Seasonal temperature averages
  • January-March: 52°F day, 16°F night
  • April-June: 80°F day, 31°F night
  • July-September: 83°F day, 45°F night
  • October-December: 67°F day, 18°F night
Seasonal rainfall averages
  • January-March: 12.20 inches
  • April-June: 12.17 inches
  • July-September: 11.54 inches
  • October-December: 13.11 inches