Best Romantic Stays in Winston-Salem
Only one property on this list carries a romantic tag: Courtyard Winston-Salem Downtown on West Fourth Street, which combines an indoor pool with a downtown location close enough to the Trade Street Arts District to walk to dinner without a car. It is not a dedicated boutique romance property, but its downtown address and indoor pool set it apart from the more business-focused chain hotels near Hanes Mall, and its valet parking suits an evening out without a car to move until checkout the next day, freeing up the whole visit for walking instead of driving.
Romantic · Winston-Salem in numbers
One Downtown Pick for Couples
Courtyard Winston-Salem Downtown sits on West Fourth Street, close enough to the Trade Street Arts District to walk to dinner and back without needing a rental car for the evening. That walkability is really the whole case for a downtown pick over a Hanes Mall hotel for a couple's trip, since nothing about the room itself is marketed specifically toward couples beyond the setting around it, which does most of the work on its own without any extra dressing-up of the amenities list on the booking page or in the marketing photos.
The property's indoor pool means a couple can plan a swim regardless of the weather outside, a useful option given how unpredictable Piedmont spring and fall temperatures can run. A quiet weekday evening at the pool, rather than a crowded weekend afternoon, tends to make for a calmer shared moment than the busier outdoor pools near Hanes Mall usually allow for on a warm summer weekend when families fill the deck chairs by mid-afternoon and the noise carries across the water well into the evening hours before the dinner reservation.
Valet parking is the only option here, a trade-off worth planning for compared with the free self-parking common at the Hanes Mall hotels, but one that suits a car-free evening downtown. Handing off the car at arrival means neither partner has to think about moving it again before checkout the next morning, freeing up the whole evening for walking instead of circling downtown blocks for a spot near a restaurant on Trade Street after dark with nowhere obvious left to park anywhere nearby once the busy evening crowd arrives downtown in force.
The Fourth Street address also puts couples within a reasonable walk of Old Salem for a daytime stroll before an evening out in the Arts District. Pairing a morning at Old Salem with an evening on Trade Street covers both a quiet historic walk and a livelier dinner scene in the same short trip without a single additional drive between the two very different halves of the day, start to finish, door to door, on foot the entire time from breakfast the first morning to the very last drink of the night before checkout.
Winston-Salem doesn't market itself as a couples' getaway destination the way a beach or mountain town might, but the compact downtown core, walkable between dinner, a gallery stop and a hotel room, gives a weekend visit the same low-friction evening that a purpose-built romance destination would otherwise promise.