The Wayside Inn – Middletown, VA
1689 Rt 11, Middletown, VA 22645
The Wayside Inn is a charming historic inn situated in Middletown, Virginia, offering a warm and welcoming atmosphere to all guests. This iconic inn dates back to the 18th century, combining traditional architecture with modern comforts. Visitors can enjoy cozy rooms, locally inspired dining, and scenic surroundings ideal for relaxation or exploration. The inn provides an authentic experience of Shenandoah Valley’s heritage and natural beauty. Guests appreciate its convenient location near outdoor activities and local attractions.
Interesting Facts:

Lodging & Overnight Stays
The Wayside Inn’s lodging service offers guests a unique opportunity to stay in a historic building that dates back centuries. Each guest room combines antique décor with modern amenities, such as Wi-Fi, plush bedding, and private bathrooms, creating a cozy and comfortable environment. Visitors appreciate waking up to views of the Shenandoah Valley’s picturesque landscape. The inn’s peaceful setting provides a restful retreat away from city noise. Whether travelers are visiting for leisure or business, the inn caters to their comfort and convenience. The attentive staff is always ready to assist with personalized service and local recommendations. Guests can enjoy access to common areas with fireplaces and relaxing seating. Staying here means experiencing Virginia’s history firsthand while enjoying today’s comforts. The inn is well suited for solo travelers, couples, and families alike. Its warm hospitality and charming atmosphere make every stay memorable.
Restaurant & Dining
The Wayside Inn’s restaurant delivers a delightful dining experience centered on fresh, local ingredients and traditional recipes. Guests can start their day with a hearty breakfast featuring seasonal fruits, eggs, and homemade baked goods. Lunch and dinner menus include classic American fare like hearty sandwiches, soups, and savory entrees inspired by regional cuisine. The cozy dining room’s rustic décor adds to the welcoming ambiance, making every meal feel special. During warmer seasons, guests enjoy outdoor patio seating surrounded by natural beauty. The restaurant accommodates dietary preferences and offers friendly, attentive service. Visitors often praise the flavorful dishes and charming atmosphere. This dining option is perfect for those who want a relaxed meal without leaving the inn. The culinary offerings showcase the Shenandoah Valley’s agricultural bounty and hospitality. Dining here complements a day of exploring local history and nature.


Event Hosting & Weddings
The Wayside Inn offers exquisite event hosting services tailored to weddings, family celebrations, corporate meetings, and reunions. Its historic charm and scenic grounds provide an elegant and picturesque setting for any special occasion. Event planners work closely with clients to create customized experiences that fit their style and budget. Facilities include both indoor and outdoor spaces, ideal for ceremonies, receptions, and cocktail hours. The inn can arrange catering, decorations, and entertainment options to enhance the celebration. Guests enjoy convenient on-site accommodations, allowing them to relax and socialize without travel concerns. The attentive staff is dedicated to flawless event execution, ensuring every detail is covered. Whether planning an intimate gathering or a grand celebration, the inn transforms visions into reality. The timeless atmosphere and personalized service make events unforgettable. Couples and hosts value the warm, welcoming environment.
Middletown, Virginia Taxi
Airport transfers, local sightseeing tours, wedding and event transportation, hotel shuttle services, winery and outdoor excursion transportation.