5 Gorgeous Historic Hotels in Winston-Salem NC

Published by Christina Riley. Last Updated on October 23, 2023.

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Did you know there are five gorgeous historic hotels in Winston-Salem, NC? Winston-Salem’s long history and reputation of preserving its important buildings mean we have many places to visit with interesting backstories.

But did you know that’s the case even with places to rest your head here?

Since we’ve been lucky enough to visit five historic Winston-Salem hotels, we wanted to share some history and more about what you can do while visiting.

After looking at each one, you can decide which Winston-Salem hotel you’ll check into for your next weekend in the Dash.

List of Historic Hotels in Winston-Salem NC

For the guide, we’ve alphabetically arranged these Winston-Salem NC hotels.

Brookstown Inn Hotel
The Graylyn Estate
Hotel Indigo
The Kimpton Cardinal Hotel
The Shaffner Inn

Skip ahead or continue reading about an amazing hotel in Winston-Salem with plenty of history.

Brookstown Inn Hotel

Address: 200 Brookstown Ave, Winston-Salem, NC
Official Website

The Brookstown Inn Hotel is actually two buildings that once made up the Arista Cotton Mill Complex dating back to 1903. It sits just steps away from Old Salem, one of the best museums in Winston-Salem, as well as an interesting historic town.

Moravians constructed the first building that makes up today’s Brookstown Inn in 1836 as a three-story brick with a monitor roof. In 1837, it opened as Salem Manufacturing Company and was one of the first mills in the South to utilize electric lighting.

The Moravian community opened the mill because they knew a large-scale cotton operation would be profitable and bring more business to the area.

The second building was a mill completed in 1880 by F & H Fries Cotton. This structure is 14 bays long with bracketed eaves and timber supports.

The mill employed 150 workers and over $125,000 in equipment. The first floor was used for weaving, the second for carding, and the third floor for spinning.

Today’s Brookstown Inn

Brookstown Inn Hotel Winston-Salem NC Image

Today, The Winston-Salem hotel captures the mill’s history and charm with elegance and hospitality. Parts of the original millworks are still visible, and the rooms have exposed wood ceilings and grand brick windows.

Historic Brookstown Inn Hotel Winston-Salem NC Image

Add all of those things together, and you’ve got one of the best hotels in Winston-Salem NC. Choose from one of the 70 guest rooms adorned with 19th-century pine floors and antique furniture.

Hand-stitched quilts cover the poster-style beds, and many suites are bi-level, featuring a decorative fireplace.

The Graylyn Estate

Address: 1900 Reynolda Rd, Winston-Salem, NC
Official Website

This historic hotel in Winston-Salem is arguably one of the city’s most luxurious.

Graylyn Estate is the former home of one-time RJ Reynolds chairman Bowman Gray and his wife Nathalie. The Norman Revival-style home was built in 1925 and originally sat on 87 acres as part of the Reynolds Plantation.

Bowman and Nathalie made Graylyn their home and decorated it to display their travels and wealth. When completed, Graylyn was the second-largest home in North Carolina to Biltmore Estate.

After Bowman’s death, Nathalie and her sons gifted the estate to Wake Forest’s School of Medicine in 1946. From 1947 to 1959, it served as a psychiatric hospital.

Bowman’s son, Gordon Gray, bought the estate in 1972 and then donated it back to Wake Forest University when the hospital threatened to sell it. Graylyn was also used as a dormitory for Wake Forest University students from 1977 to 1980.

Read More: How to Enjoy Christmas at Biltmore

Today’s Graylyn

Graylyn features 85 unique guestrooms on its vast and beautiful 55-acre estate today. Each room is uniquely decorated, so one’s experience differs upon each visit.

Quirky ironwork, stone walls, and lavish tile are some of the unique features throughout the house. You’ll get the 1930s residence feel by staying in one of the thirty-four guest rooms in the Manor House.

Groups will enjoy experiences at the Bernard Cottage, Gardener’s Cottage, or the Bungalows.

Book a night or more in the French cottage-inspired Mews for a more intimate stay. Here, you’ll find one of Graylyn’s five premium suites situated throughout the estate. They vary in size and design.

Graylyn Estate Mews — The Mews at Graylyn Estate

The premium suite in The Mews was Oprah Winfrey’s favorite during visits to her friend and Wake Forest University professor Maya Angelou. For more premium spaces, check out the Bowman Gray premium suite.

Among the ways to live in luxury include a massive king-size bed, built-in scales, a marble tub, and a seventeen-head shower. This might be our favorite hotel in Winston-Salem NC!

Hotel Indigo

Address: 104 W 4th St, Winston-Salem, NC
Official Website

What was once Downtown’s Pepper Building is now Hotel Indigo. Constructed in 1928 by Northup and O’Brien, this six-story brick building and its flat parapeted roof perfectly blend into Downtown’s Art Deco vibe.

The architects utilized a smooth cream terra-cotta against variegated brown and sandstone brickwork to bring more attention to detail. The Pepper Building was once a department store and office building.

Interestingly enough, the building also hosted a speakeasy at the bottom during Prohibition.

Today’s Hotel Indigo

Hotel Indigo Winston-Salem NC Inside Room Image

As Hotel Indigo, the Pepper Building now houses 75 boutique guestrooms, 1,600 square feet of meeting space, and Sir Winston Wine Loft & Restaurant—specializing in European-influenced Southern cuisine.

Sir Winston is another nod to the building’s past, celebrating Sir Winston Churchill and the Pepper Building’s original restaurant from more than 20 years ago.

Hotel Indigo Winston-Salem NC Sir Winston Image

Sir Winston Hotel Indigo Winston-Salem NC Image

Even though the busy department has transformed into an eclectic and stylistic hotel, the original framework of the building and details are still clearly visible.

That’s because Indigo utilizes its original floors, windows, and doors, as well as vintage signage and pendant lighting unearthed from the sub-basement.

Local art adorns every room in the hotel, which is just as important to Hotel Indigo as weaving a historical connection.

The Kimpton Cardinal Hotel

Address: 401 N Main St, Winston-Salem, NC
Official Website

The Cardinal Hotel combines the iconic and historic Reynolds Building with Kimpton, known for designing more than a place to stay.

Before it became one of the best hotels in downtown Winston-Salem, RJ Reynolds Tobacco called this Art Deco skyscraper home from its construction in 1929 through the 1970s.

Famous Brethren

From afar, The Reynolds Building looks oddly similar to the more famous Empire State Building in New York. That’s because the same architects (Shreve & Lamb) constructed both, with the Reynolds Building as the prototype.

S&L was also responsible for the Hill Building in Durham, now the 21c Museum Hotel. The Reynolds Building served as the prototype for the Empire State Building and thus, receives a Father’s Day card every year.

Nationally Recognized

Historical significance and extravagance of building materials include black marble from Belgium and a gold leaf-festooned lobby ceiling. Those features helped land the Reynolds Building on the National Register of Historic Places.

And to add some irony, tobacco may have built this structure, but it is now a smoke-free property.

Today’s Cardinal Hotel

With 174 rooms, the Cardinal Hotel offers modern accommodations, ahead-of-the-curve design, and gorgeous city views.

The interior decor reminds us of the masculinity that once dominated the building. You’ll see that through the dark blues, leather, and animal horns.

Hotels in Winston-Salem NC The Katharine inside The Cardinal Hotel Image

You’ll find a stark contrast to all this inside the hotel’s restaurant, The Katharine. Named for the Reynolds family’s matriarch, this French brasserie is one of our favorite restaurants in Winston-Salem.

It celebrates Katharine’s feminine touch and influence, well-known in her husband’s company and beyond in Winston-Salem. We mentioned her accolades, among others, in our feature on the city’s women-owned businesses.

The Shaffner Inn

Address: 150 Marshall St SW, Winston-Salem, NC
Official Website

The Shaffner Inn is circa 1907 and is a Queen Anne Tudor-styled historical hotel in Winston-Salem. Henry Fries Shaffner and Agnes Gertrude Siewers Shaffner raised their five children here until 1948.

After completing his education at the University of North Carolina, Shaffner returned to Salem (now Winston-Salem) to manage his father’s pharmacy. Later, he worked at the Briggs-Shaffner Company, known for making tobacco-cutting machines.

He also played a significant role in creating the Wachovia Loan and Trust Company in 1893, which eventually merged into the Wachovia Bank and Trust Company, becoming a central Southeastern bank.

He held key positions in this bank, including vice president and chairman of the board.

The Shaffners’ Victorian-style home, built in 1907, featured a mix of traditional and modern amenities, such as individual fireplaces in every room, central heating, electricity, and unique details like the first inward-swinging screen doors and a mantel made from wood salvaged from a collapsed log cabin in Salem.

Today at The Shaffner Inn

Today, guests can stay at The Shaffner Inn, now one of the best hotels in downtown Winston-Salem.

There are eight guest rooms in The Shaffner Inn, including a 600-foot penthouse on the third floor. Rooms are also available for meetings and events and can accommodate small weddings or corporate meetings.

Guests staying at The Shaffner Inn receive complimentary breakfast from The Founders restaurant. With some of the best shrimp and grits I’ve had in Winston-Salem, we highly recommend, at the very least, dining here if not staying.

Ready to Stay at One of these Winston-Salem NC Hotels?

While all of these original buildings were built around the same period, each Winston-Salem hotel offers something different and unique!

Whether you rest your head in luxury at Graylyn Estate or check in to a former warehouse room, we know you’ll enjoy any of these hotels in Winston-Salem, NC.

Ever stayed in one of these places? How was your time there? And if you’ve never been, which one of these historic Winston-Salem hotels will you be visiting the next time?

Let us know in the comments and don’t forget to share your adventures in our North Carolina Travel Facebook Group.