The Annual Holiday House Tour
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Artistic rendering – Event may differ

The Annual Holiday House Tour

Tour of five historic Winchester homes during the holidays.

About

Step back in time and experience the charm of Winchester's historic homes beautifully adorned for the holidays. This annual tour showcases five distinct residences, offering a glimpse into the city's rich architectural past. Complement your tour with a visit to the Bough and Dough Shop for festive decorations and baked goods, or browse unique historical books and artwork.

Our Take

Family Friendly

🎄 🎄 🎄 🎄 (4/5)

Best For

History buffs, holiday decorators, shoppers

Vibe

Historic, festive, community-oriented

Energy Level

Moderate

Budget

$$

Photo Friendly

📷 📷 📷 📷 📷 (3/5)

Weather Sensitivity

Low

Special Events & Promotions

  • Tickets available for purchase at Kimberly's and the Winchester-Frederick County Visitors Center.
  • Tickets can also be purchased at PHW’s Bough & Dough Booth during Winchester’s Winter Village weekend.
  • Free curbside pickup available for online orders by entering 'Curbside' at checkout.

Tags

holiday marketfamily friendlyhistoric preservationguided toursfestive foodholiday shoppingcommunity celebrationseasonal activitiesholiday tradition

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Location

Winchester, VA

Event Details

Pricing

$$

Duration

Varies (Shop: up to 9 hours on Sat, Tour: 4 hours)

Ages

All ages

Neighborhood

Old Town Winchester

Timed Entry

No

Organizer

Preservation of Historic Winchester, Inc.

Practical Information

Parking

PHW tries to note all parking areas available for patron parking during the tour in the map to all the tour stops. Parking is often limited, so carpooling and utilizing nearby autoparks is recommended. Visitors to the Shop at the Hexagon House may also be able to utilize Win Tran bus routes (operates Monday-Saturday).

Pet Policy

No pets allowed inside private residences. Service animals likely permitted.

Food & Drink

Baked goods, winter decorations, fresh greenery, and holiday treats available at the Bough and Dough Shop.

Quick Actions

Tips & Advice

  • Wear comfortable, low-heeled shoes as you'll be walking between historic sites and may need to remove heels inside some homes.
  • Consider carpooling or using public transportation to navigate between the historic homes, as parking can be limited.
  • Purchase advanced tour tickets for $25 to save $5 compared to the $30 price at the door.
  • The Bough and Dough Shop is free to enter and offers a great opportunity to find unique holiday gifts and decorations.
  • Check the Preservation of Historic Winchester Facebook page for any last-minute inclement weather announcements.

Frequently Asked Questions

Is the Holiday House Tour rescheduled for inclement weather?

The tour will not be rescheduled for inclement weather. Please call (540) 667-3577 or check the website and Facebook for any announcements.

Where should I start the tour?

You can start at any of the five historic home locations; each stop is a self-contained unit.

Can I visit only one house on the tour?

There are no individual tickets for single houses, but you are welcome to visit any or all of the locations.

Is photography allowed inside the homes?

No, photography is not permitted inside the private residences.

Is there a group rate for the Holiday House Tour?

Unfortunately, there is no group discount rate available for the tour.

Nearby Places (3 total)

Contributors & Updates

Last Updated: Oct 23, 2025
Original Submitter: Sep 17, 2025 The ChristmasLocal.com editorial team

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