Find hotels in Wayside, VA from $58

The best area to stay in Wayside is the Historic District, which offers a blend of historical significance and modern convenience.This area is Wayside's charming core, characterized by its well-preserved 19th-century architecture and tree-lined streets. It's highly walkable, with many local boutiques, art galleries, and acclaimed restaurants concentrated around Main Street and the Town Square. Landmarks like the Wayside Clock Tower and the old County Courthouse are focal points.For couples, the Historic District provides a romantic setting. You'll find intimate dining options, unique shops for browsing, and easy access to evening strolls through beautifully maintained public gardens like the Wayside Arboretum. Many bed and breakfasts in this area offer a cozy and personalized experience.Families will also appreciate the Historic District's central location and amenities. The Town Square often hosts community events and has open green spaces for children to play.

While Wayside can be visited year-round, the best times to go are during the spring (April to May) and fall (September to October) when the weather is most pleasant for outdoor activities.Spring in Wayside offers moderate temperatures, typically ranging from 60°F to 75°F (15°C to 24°C). This season is ideal for couples and families who enjoy exploring the area's natural beauty, such as hiking the trails in Wayside National Park or visiting the Wayside Botanical Gardens, where flowers are in full bloom. The comfortable weather makes picnics and outdoor dining particularly enjoyable.Fall also provides excellent weather, with temperatures generally between 55°F and 70°F (13°C to 21°C). The autumn foliage in Wayside is a major draw, with the surrounding hillsides displaying a spectrum of colors. This period is superb for solo travelers and couples interested in scenic drives along the Wayside Parkway or engaging in local harvest festivals. The cooler, crisp air is also suitable for longer hikes without the summer heat.

With Expedia, you earn OneKeyCash™* on eligible Wayside hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.