Winchester Vacations from $269

Things to do near Winchester

Winchester, Massachusetts offers a delightful mix of outdoor fun and family-friendly activities. Visitors can explore educational attractions, enjoy shopping at local malls and centers, and participate in unique experiences such as mansion tours and art celebrations. Don't miss seasonal events like Halloween haunts, which add a thrilling twist to your visit. Whether you're looking to relax or engage in community events, Winchester has something for everyone.

Shopping

For shopping in Winchester, visit Harvard Square, just 6 miles away, offering a vibrant mix of entertainment and family-friendly vibes. Quincy Market, 8 miles away, is another great spot for unique finds and local cuisine. If you're up for a drive, check out the Printing Office of Edes and Gill, 7 miles away.

Recreation

Experience the vibrant atmosphere at House of Blues Boston, where live music ignites the night. For sports enthusiasts, Agganis Arena offers thrilling events within a short drive. Enjoy a cultural experience at Somerville Theatre, perfect for a romantic evening or family outing, all located conveniently near Winchester.

Adventure

At LEGOLAND® Discovery Center, explore an exciting arcadeAdventureZone filled with interactive exhibits, just 5 miles from Winchester. Experience nature at Horn Pond, a serene outdoor space 2 miles away, perfect for hiking and picnicking. For thrill-seekers, Boston Paintball offers an exhilarating activity 7 miles away.

Nightlife

Experience the vibrant nightlife in Winchester by visiting Cambridge Common, a lively pub with a romantic atmosphere, just 5 miles away. Alternatively, Park-9 Dog Bar offers a fun twist on the pub scene, perfect for dog lovers seeking entertainment and a charming vibe, also 5 miles from Winchester.

Find the best attractions near Winchester

Winchester, Massachusetts, is an ideal destination for outdoor and family-themed vacations, offering a mix of urban parks, historic colleges, and fascinating sites. Visitors can delve into local culture while exploring attractions like the enigmatic Winchester Mystery House and its intriguing history, including stories of Mrs. Winchester and her bizarre mansion. With a variety of experiences available, Winchester promises a memorable getaway for those seeking city charm and family fun.

• Fenway Park: Experience the rich history and culture of one of America’s oldest baseball stadiums. Located just 8 miles from Winchester, Fenway Park offers a vibrant atmosphere where you can catch a Red Sox game or take a tour that showcases its storied past and iconic features.
• Harvard University: Just 6 miles from Winchester, Harvard University invites you to explore its beautiful campus steeped in history. Wander through the historic buildings, soak in the culture, and perhaps attend a lecture or visit the renowned museums.
• TD Garden: Situated 7 miles away, TD Garden is a hub for entertainment and business events. Attend a concert or a Boston Celtics game and enjoy the lively atmosphere that this multi-purpose arena offers.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	28.6°F (-1.9°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.8°F (-1.2°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Average
April	47.7°F (8.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.3°F (14.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	66.4°F (19.1°C)	Light Rain	Mostly Sunny	Average	Average
July	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	72.3°F (22.4°C)	Light Rain	Mostly Sunny	Average	Average
September	65.3°F (18.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	43.3°F (6.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	35.1°F (1.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Winchester

• Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
• Consider traveling to Winchester during the low season (December to February) for more affordable options.
• Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
• Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.