Winchester Vacations from $277

Things to do in and around Winchester

Winchester, Virginia, offers a delightful mix of outdoor adventures and cultural experiences. Visitors can explore scenic recreational areas, participate in local art celebrations, and enjoy special events throughout the year, including festive Halloween activities. The city also provides various tour options and opportunities for skiing, making it a perfect destination for those seeking adventure and education in a picturesque setting.

Shopping

In Winchester, visit Apple Blossom Mall for a variety of shops and family-friendly entertainment. Nalls Farm Market offers local goods, while Apple Valley Square Shopping Center has a mix of businesses. If you're up for a drive, check out nearby shopping centers for even more options.

Recreation

Experience tranquility at Jim Barnett Park, where you can enjoy serene walks and relaxation amidst nature. For outdoor enthusiasts, Rock Harbor Golf Course offers a refreshing round of golf in a beautiful setting. Don't miss Bright Box Theater for captivating performances that bring culture and entertainment to your visit.

Adventure

Experience the thrill at Summit Point Motorsports Park, located 11 miles from Winchester, where you can race and feel the adrenaline rush. For family camping, head to Watermelon Park Campground, 13 miles away, offering outdoor fun. Don't miss the excitement at North Mountain Paintball, also 11 miles from Winchester.

Nightlife

Winchester's nightlife features cozy bars and vibrant live music spots. Visit the Bright Box Theater for eclectic performances, or unwind at the Cellar Door for craft cocktails. For a fun evening, savor local brews at the Winchester Brew Works while mingling with friendly locals.

Find the best attractions in Winchester

Winchester, Virginia, is a charming destination perfect for outdoor enthusiasts and history buffs alike. Visitors can explore historic houses, scenic lakes, and significant historic sites, making it ideal for family adventures and cultural experiences. Don't miss the intriguing Winchester Mystery House and its related attractions, along with the bizarre mansion and historic estate tours, which offer a unique glimpse into the area's rich heritage.

• Shenandoah University: Immerse yourself in the vibrant atmosphere of Shenandoah University, a historic institution in Winchester. Explore its beautiful campus, rich traditions, and cultural events that reflect the dynamic spirit of the local community.
• Museum of the Shenandoah Valley: Discover the region's history and artistic heritage at the Museum of the Shenandoah Valley. This art museum features impressive exhibits, beautiful gardens, and engaging programs that highlight the area's cultural significance.
• Shenandoah Valley Discovery Museum: Perfect for families, the Shenandoah Valley Discovery Museum offers hands-on exhibits and interactive experiences that inspire curiosity and creativity in children. Enjoy a fun and educational visit for all ages.

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 slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.3°F (-0.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	34.7°F (1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	52.9°F (11.6°C)	Light Rain	Mostly Sunny	Average	Average
May	62.4°F (16.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	70.9°F (21.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.8°F (23.2°C)	Light Rain	Mostly Sunny	Average	Average
September	66.9°F (19.4°C)	Light Rain	Mostly Sunny	Average	Average
October	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
November	43.5°F (6.4°C)	Light Rain	Mostly Sunny	Average	Average
December	36.7°F (2.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average

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 during the off-peak season (typically January to March) for more affordable package holidays to Winchester.
• 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.