The Hotel Chelsea has thick load-bearing walls made of masonry, as well as wrought iron floor beams and large, column-free spaces.

[21] According to the New York City Landmarks Preservation Commission, the Chelsea's design was evocative of the demolished Spanish Flats on Central Park South.

[33] The basement measured up to 30 feet (9.1 m) deep and housed the kitchen, laundry, refrigerators, coal rooms, engines, and machinery for gas-powered and electric light.

[38] The building also attracted wealthy widows, government officials, and a variety of other middle- and upper-class professionals,[59] though Hubert refused to disclose residents' names for the social registers.

[59] In 1898, Lippincott's Monthly Magazine described the Chelsea as one of Manhattan's "literary shrines", in part because of the presence of residents such as Edward Eggleston and Jane Cunningham Croly.

[109] During that decade, the Chelsea Hotel remained popular among artists and writers because of the low rents, the friendly atmosphere, and the fact that the residences provided large amounts of privacy.

[130] By the late 1950s, the Chelsea had begun to accept black residents, starting with the printmaker Robert Blackburn, and European artists were increasingly moving in.

[131][132] By the beginning of the 1960s, the Chelsea Hotel was known as the "Dowager of 23rd Street",[33] and the surrounding area was populated with what Tippins referred to as "tawdry bars and low-rent offices".

[60] Despite Bard's cavalier attitude toward guests' activities, he closely monitored all aspects of the hotel and sometimes refused to rent rooms to people who were disruptive or those that he disliked.

[146][119] Tippins writes that Bard's inobtrusive management approach, along with the "self-directing population ... and members' willingness to live in the moment", created a strong artistic culture at the hotel.

[161] The hotel's residents included many stage and film stars, artists, and "less conventional celebrities", who stayed despite the lack of modern amenities and the presence of pests.

[181] David Bard upgraded the lobby's equipment,[64] and the family subdivided the ground-level ladies' reception room into a set of offices, but they left the ceiling murals intact.

[149] In addition, Bard was ordered to pay back $1 million and gave Marlene Krauss and David Elder control over the hotel for ten years.

[201] Real-estate experts estimated that a buyer would have to spend hundreds of thousands of dollars to renovate each room, overcoming tenant opposition and restrictions posed by the hotel's city-landmark status.

[215] Stanley Bard's son David made a bid to buy the Chelsea,[143] as did developer Aby Rosen[216] and hoteliers Ian Schrager and André Balazs.

[226][228] The Chelsea's managers ordered that all artwork be placed into storage in November, prompting more tenant complaints;[225] a rooftop garden tended by residents was also destroyed.

[238] Chetrit was ordered to fix additional building violations in May 2012[239] after tenants alleged that the renovation created toxic dust and allowed mold and rust to spread.

[259] By mid-2015, Scheetz and his partners Bill Ackman, Joseph Steinberg, and Wheelock Street Capital had spent $185 million on renovations, which were not expected to be completed for two years.

[263] MacPherson led additional renovations at the hotel, including restoration of artwork and design features,[264] as well as new public areas like a bar and spa on the roof.

[276][277] The renovation project was halted, and the New York City Department of Housing Preservation and Development mandated that the hotel's owners obtain a certificate of no harassment.

[32] The New York Times described the hotel in 2001 as a "roof for creative heads", given the large number of such personalities who have stayed at the Chelsea;[290] the previous year, the same newspaper had characterized the list of tenants as "living history".

[143] Despite the high number of notable people associated with the Chelsea, its residents typically desired privacy and frowned upon those who used their relationships with their neighbors to further their own careers.

[75] A Boston Globe reporter said that, while the hotel was internally known as an artists' residence, "those on the outside are confused by the names and the rococo facade of stories that have dragged the Chelsea down like an old roue to the bottom of history".

[159] Donna Hilts of The Washington Post wrote in 1975 that "the beatnik '50s, the hip '60s, the freaky '70s—each found a way of appreciating the freedom, the tradition and the old rug coziness of the Chelsea".

[376] The Washington Post described the hotel's lax management in 1999 as "a factor that attracted a stellar crop of artists in its century of operation",[186] while a GQ writer said the same year that "there are two Statues of Liberty on New York—the one for immigrants out by Ellis Island and the one for weirdos at 222 West 23rd Street".

Yevgeny Yevtushenko likened the smell of his room to the Dachau concentration camp,[57][86] and Arthur Miller said the decor was more akin to "Guatemalan maybe, or outer Queens" than a "grand hotel".

[145] The Associated Press wrote in 1978 that the hotel's lobby was "singularly unprepossessing", with tenants' art juxtaposed with the original fireplace,[27] while a Newsday reporter described the space as "a museum of the anarchic monstrosities of the 1960s".

[119] Terry Trucco wrote for The New York Times in 1991 that her room "got plenty of light and was oddly cheerful", though she described the furniture as old and the bathroom as "ghastly";[382] a writer for The Boston Globe said the same year that the corridors felt like "an institution in long decline".

[420] In 2019, the photographer Colin Miller published the book Hotel Chelsea: Living in the Last Bohemian Haven, which included pictures of the remaining apartments' interiors.

[421] Several pieces of fiction have been set at the hotel, such as Stuart Cloete's 1947 short story The Blast, describing New York City after a nuclear holocaust.