Alt Text Exterior view of The Historic Wayside Inn 1797 in Middletown, VA, showing the white pillared porch and historic architecture of America’s oldest continuously operating motor inn in the Shenandoah Valley.

South Wing

  • The Lee Room (Room 17) at The Historic Wayside Inn 1797 in Middletown, VA, featuring a four-poster double bed and a private bathroom with a walk-in shower.
    Lee Guest Room

    Double Bed, Bath has Shower Only

  • The Shenandoah Room (Room 18) featuring a queen bed with an ornate wooden headboard and a private bathroom with a shower at The Historic Wayside Inn 1797.
    Shenandoah Guest Room

    Queen Bed, Bath has Shower Only

  • The Massanutten Room (Room 19) at The Historic Wayside Inn 1797, featuring a classic double bed and a private full bath in Middletown, VA.
    Massanutten Guest Room

    Double Bed, Full Bath

  • Two vintage 3/4 beds in the Rutherford Room (Room 20) at The Historic Wayside Inn 1797 in Middletown, VA, with a full private bath.
    Rutherford Guest Room

    2 3/4 Beds, Full Bath

  • The Hite Room (Room 21) at The Historic Wayside Inn 1797 in Middletown, VA, featuring a four-poster double bed and a private bathroom with a walk-in shower.
    Hite Guest Room

    Double Bed, Bath has Shower Only

  • Queen bed with period-authentic wooden headboard in the Byrd Guest Room (Room 22) at The Historic Wayside Inn 1797, featuring historic decor and a private bathroom with shower in Middletown, VA.
    Byrd Guest Room

    Queen Bed, Bath has Shower Only

  • Queen-size bed with historic wood furnishings in the Wilson Room (Room 23) at The Historic Wayside Inn 1797, featuring a private full bathroom and authentic period decor in Middletown, VA.
    Wilson Guest Room

    Queen Bed, Full Bath

  • Double bed with a floral patterned and wooden bedframe in the Monroe Room (Room 24) at The Historic Wayside Inn 1797, featuring a private full bathroom and period antiques in Middletown, VA.
    Monroe Guest Room

    Short length Double Bed, Full Bath

Grand Entrance

  • Historically decorated Jubal Early Suite at The Historic Wayside Inn 1797, featuring a classic double bed and antique period furnishings in Middletown, VA.
    Jubal Early State Room

    Double Bed, Full Bath

  • The Reeves State Room at The Historic Wayside Inn 1797, featuring a King bed and elegant antique decor in Middletown, VA.
    Reeves State Room

    King Bed, Full Bath
    Adjoins The Wilkenson Room

  • The Cedar Creek Room at The Historic Wayside Inn 1797, featuring a classic double bed and 18th-century antique furniture in Middletown, VA.
    Cedar Creek Room

    Double Bed, Full Bath

  • The Wilkenson Room at The Historic Wayside Inn 1797, featuring two twin beds and antique furnishings in Middletown, VA.
    Wilkenson Room

    2 Twin Beds, Bath has Shower Only
    Adjoins Reeves State Room

  • The Middletown Room at The Historic Wayside Inn 1797, featuring a comfortable queen bed and historic antique furniture in Middletown, VA.
    Middletown Room

    Queen Bed, Full Bath

  • King-size bed in the historic Lincoln Room at The Historic Wayside Inn 1797, featuring period-authentic antiques and 19th-century decor in Middletown, VA.
    Lincoln Room

    King Bed, Full Bath

  • Cozy double bed in the historic Jefferson Room (Room 7) at The Historic Wayside Inn 1797, Middletown, VA, featuring antique wooden furniture and soft lighting.
    Jefferson Room

    Double Bed, Full Bath
    Adjoins Taylor Room

  • The Taylor Room (Room 8) at The Historic Wayside Inn 1797, featuring a classic double bed and adjoining access to the Jefferson Room in Middletown, VA
    Taylor Room

    Double Bed, Full Bath
    Adjoins Jefferson Room

  • The Harrison Room (Room 9) at The Historic Wayside Inn 1797 in Middletown, VA, featuring a classic double bed and private full bath.
    Harrison Room

    Double Bed, Full Bath

  • Queen bed and antique furnishings in the Tyler Room (Room 11) at The Historic Wayside Inn 1797, Middletown, VA
    Tyler Room

    Queen Bed, Full Bath

  • Two queen beds and a full bath in the Madison Room (Room 12) at The Historic Wayside Inn 1797 in Middletown, VA.
    Madison Room

    2 Queen Beds, Full Bath

North Wing

  • Queen bed and elegant seating area in the Rhodes Suite at The Historic Wayside Inn 1797, Middletown, VA, featuring a private full bath
    Rhodes Suite

    Queen Bed, Full Bath

  • The Bernstein Suite (Room 15) at The Historic Wayside Inn 1797, featuring a queen bed with a decorative canopy and a private full bath in Middletown, VA.
    Bernstein Suite

    Queen Bed, Full Bath

  • Two double beds in the Washington State Room (Room 16) at The Historic Wayside Inn 1797, Middletown, VA, featuring historic decor and a full private bath.
    Washington State Room

    2 Double 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.

Winter hours of operation for The Historic Wayside Inn 1797, featuring a decorative gold leaf border.
address for The Historic Wayside Inn 1797 in Middletown, Virginia, featuring a gold leaf border.
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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. 

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.

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.

Contact