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Wayside Inn

4.4(571)
Hotel

About

The Wayside Inn, operating since 1797 in Virginia’s Shenandoah Valley, offers a rare blend of historic charm and modern comfort with 22 uniquely decorated rooms featuring 19th-century antiques and private bathrooms. Its rich past includes sheltering Civil War generals and hosting presidents, making it a venue with genuine character and stories to tell.

The inn’s wood-beamed restaurant and tavern provide seamless in-house dining, ideal for business gatherings seeking a distinctive setting. With event spaces steeped in history and a welcoming atmosphere, The Wayside Inn delivers a memorable backdrop for meetings and overnight stays alike.

Best for

  • Historic venue for executive retreats
  • Intimate client dinners with character
  • Multi-night group stays with authentic charm

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

America’s oldest continuously operating inn since 1797
Historic Character
America’s oldest continuously operating inn since 1797
The inn offers an authentic experience with 22 individually decorated rooms featuring 19th-century antiques and period details. Guests walk halls once frequented by Civil War generals and presidents, creating a tangible connection to nearly three
Quaint wood-beamed restaurant and tavern
Atmosphere
Quaint wood-beamed restaurant and tavern
The on-site dining spaces feature rustic wood beams and period-inspired decor, providing a cozy, intimate setting that complements the inn’s historic ambiance and offers seamless hospitality for business events.

At a glance

Rated 4.4 on Google · 571 reviews