Upscale Bohemian.
Upscale Bohemian is the opposite philosophy of the Scandi-minimalist tier on this site. Instead of clearing the room, the owner fills it — velvet, rugs, collected objects, painted murals, brass, lamps with actual shades. The Maker is the Hudson reference; Foxfire is the Catskills reference; Urban Cowboy is the theatrical extreme. These are hotels where the room matters more than the view.
The Henson
A 2024 16-room reimagining of a 1918 Windham hotel — by the team behind Contra and Wildair.
The Reform Club
Seven rooms and a private-club energy in the middle of Amagansett. The rare Hamptons hotel that actually feels like a clubhouse.
Doctor Sax House
A 1874 Prohibition speakeasy turned nine-room boutique, run by Kelly and Bryan Binder. Café on the ground floor.
Foxfire Mountain House
Layered, lived-in, and photographed a thousand times on Instagram — but earns it.
Granville House
Five rooms, Michelin Key, run by former New York restaurant pros. George Bailey's house, sort of.
Hotel Dylan
A Woodstock native's Novogratz-designed revival of a '70s bi-level motel. Turntables in every room.
The Christopher
Nine rooms in a white-clapboard historic, reworked with Art Deco geometric wallpapers and aqua tile.
The Herwood Inn
Four suites named for iconic female musicians — Carole, Aretha, Joni, Stevie.
The Hudson Milliner
A guesthouse run by two Brooklyn artists — original work in every room.
The Maker Hotel
Theatrical, layered, and collected — the Maker is a mood you can book.
Twin Gables
Woodstock's community-minded eclectic — like staying with an artist friend.
Urban Cowboy Catskills
A 19th-century Alpine Inn reborn as Nashville-in-the-Catskills. Copper tubs included.
Zey Hotel
Zach Erdem's art-forward 10-room boutique — the opposite of generic Southampton chintz.
Garden Gables Inn
An 18-room classic on five acres walking distance from Lenox Village, recently freshened up.
The Charm on Main
An adults-only 22-room historic, originally built as a school for charm and personality. We are not making this up.
The Reluctant Panther
A 100-plus-year-old inn at the heart of Manchester Village — the region's most serious small luxury hotel.
The Stewart House
An 1883 Italianate boarding house on Athens's waterfront. Nine rooms, Art Deco bar, wood-fired tavern.
The Veranda House
A historic inn overlooking the harbor — rebuilt with care after the 2022 fire that took the old one.