
Good design comes in a lot of shapes and sizes. There's the sleek and elevated kind. The simple and safe kind. The kind meant to shock you. And then there's the kind that makes you smile the second you walk in, the lighthearted, unexpected, delight-first kind. Call it whimsy.
These ten boutique stays prove that good design doesn't have to take itself so seriously. Playful color, unexpected detail, and a sense of humor go a long way.

Hotel Saint Vincent occupies a red brick 1861 building in New Orleans' Lower Garden District that once housed an infant asylum. The interiors mix art deco, midcentury, and 20th century Italian influences, with moody dark rooms giving way to bathrooms lined in pink and red tile and custom psychedelic wallpaper. The courtyard pool sits under sky blue verandas, and the Chapel Club glows with neon signage and a hot pink velvet bar.

The Madrona sits inside an 1881 Victorian mansion in Healdsburg, restored with a nod to the Aesthetic Movement's belief in art and beauty for their own sake. Antiques original to the property mingle with bold new wallpaper, sculptural lighting, and saturated color throughout the gabled house and its wraparound porches.

Ulysses Hotel fills a 1912 apartment building in Baltimore's Mount Vernon with a maximalist mix of Art Deco movie palace glamour, Victorian detail, and 1920s ocean liner style. Expect canopy beds, hand-beaded lampshades, flamingo motifs throughout, and a mirrored cocktail lounge with the feel of an early disco.

Anna & Bel transformed an 18th century former women's asylum in Philadelphia's Fishtown into a warm, curved retreat with sage, terra-cotta, and amber tones throughout. Original brick walls and wood beams stay exposed, and a courtyard pool framed by a wraparound balcony echoes the balconies of New Orleans' French Quarter.

Crosby Street Hotel brings Kit Kemp's signature maximalism to SoHo, with a gallery-like lobby anchored by sculpture from artists like Fernando Botero and Jaume Plensa. Floor-to-ceiling windows flood the rooms with light, and no two are alike, each layered in bold pattern, color, and Kemp's playful custom textiles.

The Lafayette Hotel channels the grand hotels of the early 1900s inside its restored 1946 building in San Diego. The lobby is gilded with plastered crown molding, vintage checkered marble floors, and crystal chandeliers under a glass atrium, while the rooms carry a botanical, slightly gothic wallpaper throughout.

The Georgian returned its 1933 Art Deco building on Santa Monica's Ocean Avenue to its original turquoise glory. Inside, original crown moldings, medallions, and archways pair with burnished brass, plush velvet, and imported Italian marble for a look designers call Havana Art Deco.

Hotel Bardo reimagines an 1888 Victorian mansion in Savannah through what its designers call deliberate maximalism, layering saturated color and playful pattern against preserved historic detail. A palm-lined courtyard pool evokes an Italian lido, and a tucked away pink room glows under a pink glass chandelier.

Fouquet's brought its Parisian roots to Tribeca through designer Martin Brudnizki, who dressed the hotel in Art Deco inspired lavender and pistachio tones. Custom Toile de Jouy wallpaper, parquet floors, and violet marble bathrooms give the rooms a residential, distinctly French feel.

Faraway Martha's Vineyard reworked the historic Kelley House into a mid-century inspired retreat with a warm, sandy palette and a botanical touch throughout. Floor-to-ceiling drapery reveals oversized cabinetry stocked with curiosities, and a fluted marble fireplace anchors the double-height lobby.
Whimsy might be the hardest kind of design to pull off well. It asks a space to be beautiful and a little bit fun at the same time, and every one of these ten manages it.
All ten hotels are bookable through Journey, our rewards partner for boutique and independent stays. Members earn points on direct bookings, plus perks like member rates, suite upgrades, and personalized recognition at the kinds of hotels worth being a regular at. Get your complimentary Journey membership here and start earning points on stays like these.
Mentioned in this article
Places and collections from the piece

The Madrona Hotel
Healdsburg, California

Ulysses Hotel
Mount Vernon, Baltimore, Maryland

The Lafayette Hotel and Club
University Heights, San Diego, California

The Georgian
Santa Monica, California

Crosby Street Hotel
New York, New York

Hotel Bardo
South Historic District, Savannah, Georgia

Hotel Saint Vincent
Lower Garden District, New Orleans, Louisiana

Faraway Martha's Vineyard
Edgartown, Edgartown, Massachusetts

Fouquet's
New York, New York

Anna & Bel
North Philadelphia, Philadelphia, Pennsylvania