Wayside Inn

The Wayside Inn is a gem. From the warm, accommodating staff to the incredible atmosphere, it offers an experience unlike anything else in the area. Every corner of the inn feels special, with a real “if these walls could talk” kind of charm. That said, if you’re looking for perfectly uniform guest rooms, oversized TVs, or instant hot water the second you turn on the shower, this may not be your style. But if you appreciate character, history, and genuine comfort, you’ll absolutely love it. I can’t recommend it highly enough.

I've been staying at the Wayside Inn at least 4 times a year since 2018. I make it a point to stay here whenever I travel through the Shenandoah valley. It is a lovingly preserved relic of Old Virginia history. The bedrooms are very large, in fact, most of them are multi-room suites, filled with antiques, old pictures of long ago American Heroes, and the vibe is one of peace, relaxation, quiet, and a deep reverence for the past. The public rooms on the first floor are picture book museum settings of beautiful colonial furniture, elegant and comfortable, with historical portraits of long forgotten individuals staring at you from deep in the past. There are history books of every description all over the Inn for you to get lost in as you drift off to sleep. The "Summer Kitchen" which is one

Thank you so much for the wonderful stay. The atmosphere of the hotel is truly historical, with very beautiful décor and pictures that reflect the charm of old times. The design is unique and full of character. The staff are extremely friendly and welcoming, the service is excellent. I am very, very happy that I had the chance to be your guest and truly enjoyed my stay.

We recently celebrated our wedding reception at the Wayside Inn, and it was nothing short of magical. This beautiful historic inn is full of character, charm, and timeless elegance—every corner of the property tells a story, and it provided the perfect setting for our special day. What truly set the experience apart was the amazing staff, especially Brittany, the property manager. From the very beginning, Brittany was attentive, organized, and incredibly kind. She guided us through the planning process with professionalism and genuine care, making sure every detail was just right. On the day of the event, she and her team made everything run seamlessly—we didn’t have to worry about a thing. Our guests couldn’t stop raving about the venue. The indoor spaces were warm and inviting, and the

This is an absolutely amazing. very old inn that is full of charm, character and a long history!! They will be reopening the restaurant in October. There are 5 separate dining areas from casual to formal. Two sitting rooms, a wedding venue and several outside seating areas. There are 21 rooms all with period antiques. The staff are just wonderful! Jessica gave us the full tour which we so appreciated. There are about 20 wineries within 30 minutes of here as well as the town of Winchester. We'll be back with a bunch of friends for a few nights to take it all in!