The Art of the Historic Hotel

By AHL on 06.18.26

Few places tell the story of a destination like a historic hotel. Some remain museum-like landmarks, but the most compelling are still alive—welcoming guests, adapting over time, and quietly adding new chapters to histories that began generations ago. What sets them apart isn’t just architectural pedigree or a famous guest list, but a deeper connection to place that can’t be replicated overnight. This summer, we’re checking into rooms with a past.

The Fifth Avenue Hotel

This stunning mansion on the corner of 28th and Fifth started life as the home of Charlotte Goodridge, a fixture of Gilded Age society. In 1907 it was sold and rebuilt as a five-story Renaissance palazzo by infamous architecture firm McKim, Mead & White—first a bank, now the heart of the 153-room hotel. The current owner, Alex Ohebshalom, spent the better part of the last decade restoring the brick and limestone and its original terra-cotta cornice, then set a new 24-story glass tower where the carriage house once stood. Martin Brudnizki was brought on to work design magic the way only he can, pulling inspiration from the building’s history and Ohebshalom’s travels to Marrakech, Laos, and Myanmar: hand-painted wallpaper, silk-ruched elevators, velvet, tassels, and a color palette of garden greens, peony pinks, and buttercup yellows. The result reads less like a hotel than the home of a wild and worldly collector. Read our full review here.

Highlight: The Portrait Bar, where people gather over Darryl Chan’s cocktails and the street noise drops away the moment you step inside.

The Fifth Avenue Hotel | 1 West 28th Street, Manhattan, New York

The Pridwin Hotel & Cottages

First opened in 1927, The Pridwin is the last of the grand summer resorts on Shelter Island, and is no stranger to grandeur. (It takes its name from the shield of King Arthur.) The Queens Company Ltd. built it between 1924 and 1926, ran out of money, and lost it to one of the contractors, Francis Myers. The Petry family bought the place in 1961 and held it for six decades before partnering with Cape Resorts, who spent two years gutting and restoring it. Behind the white clapboard and hunter-green casements, the original hardwood floors are here, along with a 1927 chandelier rewired and rehung. It reopened in 2022 with 33 rooms and 16 cottages spread across nearly ten wooded acres, perched on a rise above Crescent Beach. All in, it’s just a five-minute ferry from Sag Harbor.

Highlight: Summer 2026 looks particularly promising. Château Minuty is rolling out their cart for sunset rosé on the lawn, while Dante’s team is mixing cocktails in their summer pop-up. Sunday evenings will bring Mahjong & Martinis on Crescent Beach, and the older rhythms still run solidly in the DNA. Tennis and croquet, the saltwater pool, live music down in the Grove, s’mores and nature walks into the Mashomack Preserve next door.

The Pridwin Hotel & Cottages | 81 Shore Rd, Shelter Island, New York

The Omni Parker House

The hotel opened on School Street in 1855 and hasn’t closed since, which makes it the longest continuously operating hotel in the country. Harvey Parker, a near-penniless farm boy from Maine, razed the old Mico mansion and put up a five-story marble-and-brick hotel in its place; the building you walk into today dates to 1927, with one wing kept running through construction so the doors never shut. The Saturday Club met here monthly (Emerson, Hawthorne, Longfellow, Holmes), and it’s where Dickens gave his first American reading of A Christmas Carol. Malcolm X bused tables, and JFK proposed to Jackie at table 40 in Parker’s Restaurant. A renovation begun in late 2024 has since run through all 551 rooms and 23,000 square feet of meeting space, with new marble in the lobby and carpets woven with the Parker House crest.

Highlight: Boston Cream Pie—Massachusetts’ official dessert—and the Parker House roll were both invented in this kitchen, and they’re still here. Downstairs, The Last Hurrah pours cocktails and Bostonian whiskey behind floor-to-ceiling windows, named for the 1956 novel about the city’s most colorful mayor.

The Omni Parker House | 60 School Street, Boston, Massachusetts

Pendry Chicago

Set in the 1929 Carbide & Carbon Building, this gold-domed Art Deco landmark was nicknamed the Champagne Bottle by Chicagoans. Pendry Chicago is a stay with real history under the celebratory polish — its 364 rooms are threaded with Jazz Age detail and just steps from the Riverwalk and the Magnificent Mile. Take the ride 24 floors up to Château Carbide for spritzes, weekend DJs, and skyline.

Highlight: We’re checking in for Venteux alone: go for the French brasserie’s champagne list, stay for the $1 oyster Tuesdays.

Pendry Chicago | 230 N Michigan Avenue, Chicago, Illinois

COMO Castello Del Nero

The castle goes back to the twelfth century, when it became the country seat of the Del Nero family, a noble Florentine line whose rearing-greyhound crest still turns up around the estate. It passed through owners for centuries and had drifted toward ruin before a Del Nero descendant, Carlo Torrigiani, and his American wife, Anna Frey, pulled it back—restoring the frescoes and mosaics under the supervision of Italy’s Fine Art Commission and opening it as a hotel in the mid-2000s. COMO bought the whole 740-acre estate in 2018 and reopened it the following year as its first property in continental Europe, with Milanese designer Paola Navone laying a cool, pared-back modern layer over the original terracotta floors, fresco walls, and vaulted ceilings. It sits in the heart of Chianti, halfway between Florence and Siena, with 50 rooms and suites and vineyards and olive groves running to the edges.

Highlight: The olive grove dinner—the estate’s signature, a monthly barbecue laid out among the trees from April to September, and the one guests single out.

COMO Castello Del Nero | Strada Spicciano 7, Tavarnelle Val di Pesa, Tuscany

Hotel Sacher Vienna

The hotel that grew out of a cake. In 1832 a sixteen-year-old apprentice, Franz Sacher, improvised a dessert of chocolate sponge, apricot jam, and dark glaze for Prince Metternich’s guests—the Original Sacher-Torte, still made to the same recipe. His son Eduard opened the Hotel Sacher across from the Vienna State Opera in 1876, and Eduard’s widow, Anna Sacher—a cigar-smoking grande dame who bred French bulldogs—ran it for nearly forty years and made it the meeting place of imperial Vienna. The Gürtler-Winkler family has held it since the 1930s and runs it still, the only family-owned luxury hotel in the city, with 152 rooms and suites recently named to the World’s 50 Best Hotels.

Highlight: The Original Sacher-Torte itself—chocolate, apricot, and a recipe guarded since 1832—best taken with a coffee at Café Sacher.

Hotel Sacher Vienna | Philharmoniker Strasse 4, Vienna, Austria

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