South Wing
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Lee Guest Room
Double Bed, Bath has Shower Only
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Shenandoah Guest Room
Queen Bed, Bath has Shower Only
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Massanutten Guest Room
Double Bed, Full Bath
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Rutherford Guest Room
2 3/4 Beds, Full Bath
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Hite Guest Room
Double Bed, Bath has Shower Only
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Byrd Guest Room
Queen Bed, Bath has Shower Only
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Wilson Guest Room
Queen Bed, Full Bath
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Monroe Guest Room
Short length Double Bed, Full Bath
Grand Entrance
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Jubal Early State Room
Double Bed, Full Bath
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Reeves State Room
King Bed, Full Bath
Adjoins The Wilkenson Room -
Cedar Creek Room
Double Bed, Full Bath
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Wilkenson Room
2 Twin Beds, Bath has Shower Only
Adjoins Reeves State Room -
Middletown Room
Queen Bed, Full Bath
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Lincoln Room
King Bed, Full Bath
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Jefferson Room
Double Bed, Full Bath
Adjoins Taylor Room -
Taylor Room
Double Bed, Full Bath
Adjoins Jefferson Room -
Harrison Room
Double Bed, Full Bath
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Tyler Room
Queen Bed, Full Bath
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Madison Room
2 Queen Beds, Full Bath
Stay Somewhere With a Story
Nestled in the heart of Virginia’s Shenandoah Valley, the Historic Wayside Inn has been welcoming travelers to Middletown since 1797.
For more than two centuries, guests have gathered, celebrated, dined, and rested within these walls. Today, the Wayside continues that tradition with the same sense of warmth and hospitality that has made this historic inn a special place to stay for generations.
A Stay Unlike Any Other
No two rooms at the Wayside are quite the same. Our 22 individually decorated guest rooms are filled with historic character, period details, and antique furnishings, each with its own personality and story.
Here, history isn’t something you simply come to see. It’s something you get to stay in.
Settle in for a quiet weekend in the Shenandoah Valley, enjoy dinner just downstairs at Clem’s Kitchen, wander through historic Middletown, or simply slow down and enjoy the charm of a place that has welcomed generations of travelers before you.
More Than a Place to Stay
Over the years, the Wayside Inn has become part of countless stories, from weekend getaways and family traditions to weddings, celebrations, and return visits year after year. Our historic gathering spaces continue to offer a one-of-a-kind setting for moments both intimate and grand.
And no stay at the Wayside is complete without gathering around the table. Located right here at the inn, Clem’s Kitchen is a welcoming, from-scratch restaurant serving breakfast, lunch, dinner, and Sunday brunch throughout the week. Whether you’re starting your morning before exploring the Shenandoah Valley, settling in for dinner after a day away, or joining us for a leisurely weekend brunch, you don’t have to venture far for a good meal.
Come Stay Awhile
Some places are simply where you spend the night. Others become part of the reason you traveled in the first place. Come experience the history, character, and hospitality of the Wayside Inn for yourself.
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Featured In
Backroads Magazine
First Place 2025 "Best Of" as seen in January 2026 Volume 32 No 1
It's a Southern Thing
The most haunted hotel in every Southern state- Virginia
Washington Post
"Wayside Inn Gives... Catalyst to Community Development" (April 10, 1969) Article is behind a paywall
everyday Amenities
Board Games
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All day Coffee & Tea
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Courier
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Gardens
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Valet to room
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Connecting rooms
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After Hours Door
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Parking Lot
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cable tv
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gift shop
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Frequently asked questions
What is Wayside Inn's Cancellation Policy?
Our cancellation policy is as follows:
If a reservation is cancelled within 24 hours of making said reservation, or up to 14 days before arrival, there is no penalty. If cancelled 14 to 2 days before the scheduled arrival, there is a 50% refund. If cancelled within 2 days of arrival, there is no refund. Please call if you have any questions or concerns about making a reservation.
If you are able to move your reservation to a different time, cancellation fees can be avoided.
How can we make dinner reservations?
Please call Clem’s Kitchen for dinner reservations. They can be reached at 601-301-2536 Thursday-Sunday. Follow them on facebook for the most up to date hours of operation.
What is your pet policy?
Bring your best friend along! We are delighted to offer three specially designated pet-friendly rooms for guests traveling with their four-legged companions.
Standard Pet Stay: A fee of $25 per night applies.
The Elevated Pet Experience: Treat your pet to a little extra pampering! You can find this premium upgrade under our Exclusive Offers.
Service Animals: Service animals are always welcome in any of our guest rooms.
A Note for Allergy Sufferers: While we perform deep cleanings after every pet stay, the historic nature of our Inn makes it impossible to guarantee a 100% dander-free environment. We encourage guests with extreme sensitivities to keep our pet-friendly status in mind when booking.






