Hotels in Winchester, Massachusetts

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Best hotels in Winchester

Winchester overview

Winchester is an inviting destination that has something for everyone. Winchester might not have well-known attractions within the city, but you won't need to venture far to find top places to visit like Harvard Square and USS Constitution Museum. Popular sights in the surrounding area include TD Garden and Fenway Park.

Where to stay in Winchester

Whether you're planning a longer vacation or a weekend getaway, Winchester has the right hotel for you. You can shop as many as 2914 deals for Winchester accommodations on, some with discounts of up to 45%. We have room prices starting at 49 USD per night and below you'll find the number of hotels by star rating in Winchester as well as in the surrounding area:
  • • 15 5-star hotels from 197 USD per night
  • • 303 4-star hotels from 149 USD per night
  • • 224 3-star hotels from 115 USD per night
  • • 30 2-star hotels from 70 USD per night

How to get to Winchester

Fly into Boston, MA (BOS-Logan Intl.), 8.9 mi (14.3 km) from central Winchester.

Train stations include:
  • • Winchester Station (0.5 mi/0.8 km from the city center)
  • • Winchester Wedgemere Station (0.6 mi/1 km from the city center)

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
Here are some top sights in the surrounding area:
  • • Harvard Square (5.6 mi/9 km from the city center)
  • • USS Constitution Museum (7.1 mi/11.5 km from the city center)
  • • TD Garden (7.4 mi/11.9 km from the city center)
  • • Fenway Park (7.7 mi/12.4 km from the city center)
  • • Boston Public Garden (7.8 mi/12.6 km from the city center)

When to visit Winchester

If you're beginning to plan your vacation, you might be wondering when is the best time to visit. Here are the seasonal norms to help you decide when to go:

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