Hotels in Winchester, Massachusetts

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Winchester overview

Winchester is special for its sports, and known for its college atmosphere and shops. You're sure to find the coffee and bar options to your liking. 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

Featuring accommodation choices that can meet everyone's needs, Winchester is the place to go. There are 391 hotels in the Winchester area and you can shop as many as 118 deals for rooms on, some with discounts of up to 40%.
  • • 39 2-star hotels with an average price of $66 per night
  • • 183 3-star hotels with an average price of $105 per night
  • • 127 4-star hotels with an average price of $129 per night
  • • 15 5-star hotels with an average price of $199 per night

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:
  • • Agganis Arena
  • • TD Garden
  • • Fenway Park
  • • East Boston Memorial Stadium
  • • Alumni Stadium
Known for its family-friendly sights such as:
  • • Artisans Asylum
  • • New England Aquarium
  • • Franklin Park Zoo
  • • Andover Bird Sanctuary
  • • Salem Toy Museum
It's notable for its swimming spots and favorite places for nature lovers that include:
  • • Revere Beach
  • • Wayland Town Beach
  • • Saxonville Beach
Whether window-shopping or searching for a perfect souvenir, here are some favorite shopping areas:
  • • Woburn Mall
  • • Burlington Mall
  • • Square One Mall
  • • Cambridgeside Galleria
  • • Faneuil Hall Marketplace
Enjoy the university setting or the collegiate vibe around the area of:
  • • Harvard Law School
  • • Harvard Science Center
  • • Harvard Graduate School of Design
  • • Harvard University
  • • Bentley College
Some popular places in the area to visit include:
  • • Harvard Square
  • • USS Constitution Museum
  • • Boston University
  • • Boston Public Garden
  • • Hynes Convention Center

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: 12.0 inches
  • • April-June: 12.2 inches
  • • July-September: 11.5 inches
  • • October-December: 13.1 inches