Hotels in Winchester

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Winchester overview

Featuring picturesque views of mountains and flowers, Winchester is known for its natural features and sports. Sports fans will enjoy football. 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 a longer holiday or a weekend getaway, Winchester offers accommodation to suit your needs. You can shop for as many as 2530 deals for Winchester accommodation on, some with discounts of up to 65%. We have room prices starting at GBP 26 per night. Below, you'll find the number of hotels for each star rating in Winchester as well as in the surrounding area:
  • • 15 5-star hotels from GBP 118 per night
  • • 361 4-star hotels from GBP 70 per night
  • • 231 3-star hotels from GBP 58 per night
  • • 29 2-star hotels from GBP 44 per night

How to get to Winchester

Fly into Bedford, MA (BED-Laurence G. Hanscom Field), 7.2 mi (11.5 km) from central Winchester. Boston, MA (BOS-Logan Intl.) is the next-closest major airport, 8.9 mi (14.3 km) away.

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

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. Top spots for nature lovers include:
  • • Mystic River Reservation
  • • Royall Park
  • • Logan Park
  • • Magoun Park
  • • Prospect Hill Park
Here are some of the top sights in the surrounding area:
  • • Harvard Square (5.6 mi/9 km from the city centre)
  • • USS Constitution Museum (7.1 mi/11.5 km from the city centre)
  • • TD Garden (7.4 mi/11.9 km from the city centre)
  • • Fenway Park (7.7 mi/12.4 km from the city centre)
  • • Boston Public Garden (7.8 mi/12.6 km from the city centre)

When to visit Winchester

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

Seasonal temperatures
  • • January-March: 11°F day, -9°F night
  • • April-June: 27°F day, 0°F night
  • • July-September: 28°F day, 7°F night
  • • October-December: 19°F day, -8°F night
Seasonal average rainfall
  • • January-March: 306 inches
  • • April-June: 309 inches
  • • July-September: 293 inches
  • • October-December: 333 inches