Where the Artists Go: Under the Radar Spots in Six Storied Creative Colonies

By AHL on 08.10.26

You know the saying. First come the artists, then comes… everyone. Whatever draws creatives to a higher plane — the light, the vibe vortex, the space, the weather — when like-minded visionaries congregate in a beautiful place, it means something good is happening energetically. For generations, certain spots have stirred the imagination and drawn magic-making communities into building a homebase for the long (creative) haul. Here, AHL discovers our favorites, and the rooms that drop you right in the middle.

Alila Ventana Big Sur

The light on these cliffs has pulled artists to Big Sur since Henry Miller first set up camp, and Alila Ventana keeps that wild creative streak going across 160 acres of redwood and meadow — just 54 rooms in all. We spend the days the way this NorCal enclave asks: a photography workshop, a foraging hike, a tarot reading under the trees. The spa’s outdoor couples’ cabanas open into the redwood canopy, and the clothing-optional Mountain Pool sits high enough to be its own hidden world. Dinner is Mediterranean-Pacific at The Sur House, or a private tasting at the Glass House, suspended above the coast.

Alila Ventana Big Sur | 48123 Highway One, Big Sur, California

Marrero’s Guest Mansion

Key West has been collecting writers since Hemingway typed upstairs on Whitehead Street and Elizabeth Bishop kept a house on the island. We stay at Marrero’s, a Victorian mansion a cigar maker built for his family in 1890, now twelve rooms hung with hand-picked art in the middle of Old Town. Duval Street is half a block away, the pool waits under the palms, and the front porch does exactly what Key West porches are for. Tennessee Williams and Robert Frost worked here too; the light that kept them is free.

Marrero’s Guest Mansion | 410 Fleming Street, Key West, Florida

Addison Choate

As one of the four towns that make up Massachusetts’ Cape Ann — an institution in itself of history, nautical bohemianism, and coastal creative life — Rockport has been a haven for artists and artisans for a century. (Motif No. 1 — the red fish shack on the harbor — may be the most painted building in America, at least at its square footage.) Settle into Addison Choate, an 1851 colonial on Broadway listed on the National Historic Register, and one of our top favorite stays of the year, with nine rooms and a pair of carriage-house suites you will have a hard time leaving, layered with Persian rugs and original art (historic and local). The porch opens onto perennial gardens, and the local gallery stroll of Bearskin Neck and the Rockport Art Association are a 10-minute walk away.

Addison Choate | 49 Broadway, Rockport, Massachusetts

The Highliner

Also in Cape Ann and 15 minutes from Rockport, painters have worked Gloucester’s light for two centuries — Fitz Henry Lane from his ledge above the harbor, Edward Hopper, and the summer Avery, Gottlieb, and Rothko painted side by side. The Highliner is brand spanking new this spring, putting us in the middle of America’s oldest seaport and directly on Main Street proper: eleven rooms, a few of them two-story lofts, all in sultry nautical tones. The working waterfront and the Cape Ann Museum’s Lane collection are a short walk in either direction, the check-in is keyless, (but the What’s App is constant). After checking out the classics, take the water shuttle to the original — and still highly inhabited — art colony of Rocky Neck, then head over to Eastern Point for a tour of Beauport, Sleeper McCann House, the designer’s mecca of early-20th century eclecticism.

The Highliner| 110 Main Street, Gloucester, Massachusetts

The Porches Inn

North Adams built its whole second life around MASS MoCA, and the contemporary-art museum sits directly across the street from us. We take a row of restored Victorian mill houses — the porches that name the place lined with rocking chairs, a heated pool and sauna out back, Studio 9 hosting intimate sets down the block. Mount Greylock rises behind town for the days you want a trail instead of a gallery. It’s the Berkshires with the art turned all the way up, and the museum is a two-minute walk from the porch.

The Porches Inn | 231 River Street, North Adams, Massachusetts

Twin Gables of Woodstock

Before the rock n’roll legacies began in the 1960s, Woodstock was an artists’ town since 1902, when the Byrdcliffe colony went up in the hills and drew free spirits from everywhere. Twin Gables has been part of it nearly as long — artists turned this 1880s Victorian into a hotel in 1926; a century later, the vibes are still pure upstate bohemian. Snag one of the of ten rooms, each its own jewel box of color and hand-picked art, head to the rooftop terrace among the treetops, and warm baked goods in the sunny kitchen. Historic Tinker Street and world-class restaurants are at your feet, and The Catskills trails and the Ashokan Rail Trail start close by. Plans for prime leaf-peeping and the Woodstock Film Festival upcoming in October.

Twin Gables | 73 Tinker Street, Woodstock, New York

Have you signed up for our weekly newsletter yet? Never spammy, always bringing you the best and coolest hotels in the world and global lifestyle culture, all through the eyes of industry insiders and local tastemakers. Sign up here!