Winchester Vacation Packages

Things to do in and around Winchester

Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers alike, offering a range of activities such as golfing, skiing, and various recreation opportunities. Visitors can explore scenic landscapes and engage in exciting shore excursions, making it an ideal spot for memorable Winchester trips. Whether you're looking for a relaxing getaway or an action-packed adventure, Winchester has something to suit every traveller's taste.

Shopping

For a delightful shopping experience in Winchester, visit Apple Blossom Mall for a variety of stores and entertainment. Nalls Farm Market offers local goods, while Apple Valley Square Shopping Center combines business and family vibes. If you're up for a drive, explore nearby shopping options for even more choices.

Recreation

Enjoy a round of golf at Rock Harbor Golf Course, where you can embrace the outdoor vibes amidst beautiful landscapes. For relaxation, visit Jim Barnett Park, perfect for unwinding in nature. Don't miss a show at Bright Box Theater, offering a charming atmosphere for culture and family entertainment.

Adventure

Summit Point Motorsports Park offers thrilling motor racing experiences, located 17.7km from Winchester, perfect for adrenaline seekers. For a family-friendly adventure, Watermelon Park Campground, 20.9km away, provides an outdoor haven. Tuckers Lane Trailhead, 32.2km from town, invites hikers to explore scenic trails amidst nature.

Nightlife

Winchester offers a charming nightlife with venues like the vibrant Loudoun Street, perfect for a casual stroll. Try the lively atmosphere at the recently renovated 50/50 Taphouse or enjoy live music at the Bright Box Theater for a delightful evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Winchester

Winchester, Virginia, offers a delightful blend of outdoor adventures and rich history, making it perfect for family-friendly vacations. Explore historic houses and scenic lakes, and immerse yourself in the local culture at various attractions. Whether you're interested in discovering Winchester's storied past or enjoying its beautiful landscapes, there's something for everyone. Don't miss out on the popular attractions and resorts in the area to enhance your visit.

• Shenandoah University: Immerse yourself in the vibrant atmosphere of Shenandoah University, a historic institution that showcases the rich educational culture of Winchester. Explore its charming campus, filled with local art and events that reflect the community's spirit.
• Museum of the Shenandoah Valley: Experience a captivating blend of art and history at the Museum of the Shenandoah Valley. This art museum features stunning exhibitions that highlight the region's cultural heritage, making it a perfect spot for art enthusiasts.
• Shenandoah Valley Discovery Museum: Delight in family-friendly fun at the Shenandoah Valley Discovery Museum, designed for children. Engage in interactive exhibits that inspire curiosity and learning, fostering a love for exploration in young minds.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, 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.