Historic Inn / Boarding House.
Many of the region's best hotels started as boarding houses — places where 19th-century travelers (and 20th-century Catskills vacationers) actually stayed. Kenoza Hall (1880), The Arnold House, The Six Bells, The Maker. Restoration here means keeping the room count honest, the staircase intact, and the front porch working.
Birchwood Inn
An 1857 Greek Revival on Hubbard Street, relaunched in 2022 by Seth Johnson and Russell Lange.
ButtonBall Inn
Tucked into the historic village of South Egremont. Cozy meets curious.
Candleberry Inn
An 18th-century sea captain's home, restored in 2016 by its New York owners. AAA Four Diamond, 2025.
Doctor Sax House
A 1874 Prohibition speakeasy turned nine-room boutique, run by Kelly and Bryan Binder. Café on the ground floor.
Dorset Inn
Vermont's oldest continuously operating inn — on the Dorset Green since 1796.
Foxfire Mountain House
Layered, lived-in, and photographed a thousand times on Instagram — but earns it.
Garden Gables Inn
An 18-room classic on five acres walking distance from Lenox Village, recently freshened up.
Granville House
Five rooms, Michelin Key, run by former New York restaurant pros. George Bailey's house, sort of.
Greyfinch Chatham Inn
A quietly restored inn in the middle of Chatham, leaning clean New England rather than nautical.
Hotel Darby
A Main Street historic in Livingston Manor, quietly renovated.
Hotel Kinsley
A 42-room hotel scattered across four historic Kingston buildings.
Hotel Lilien
An intimate Tivoli historic, restored with restraint.
Hudson Whaler
A restored Hudson historic, 2024's Best of Hudson Valley winner.
Kenoza Hall
A whitewashed 1880 boarding house overlooking a lake. 55 acres, 10 bungalows.
Martin's Guest House
Thirteen rooms on Centre Street, family-run for decades. Breakfast on a porch overlooking a garden.
Rookwood Inn
An 1885 painted-lady Victorian on Old Stockbridge Road, relaunched in 2022. Sister property to the Birchwood.
Sea Street Inn
Nine rooms, four-season, somebody actually cooks your breakfast. The opposite of a Cape Cod Comfort Inn.
The Amelia Hudson
A 19th-century Queen Anne on a quiet Hudson side street.
The Arnold House
A former tavern on Shandelee Mountain — Foster Supply's first.
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 Christopher
Nine rooms in a white-clapboard historic, reworked with Art Deco geometric wallpapers and aqua tile.
The Edgartown Inn
A 1798 whaling captain's house where Hawthorne and Webster both stayed. Still operating. Still quiet.
The Four Columns Inn
Reopened June 2025 on the Newfane village green — a Greek Revival inn with an 1832 tavern attached.
The Grafton Inn
An 1801 inn in a restored village preserved by a Vermont non-profit. The whole town is the hotel.
The Henson
A 2024 16-room reimagining of a 1918 Windham hotel — by the team behind Contra and Wildair.
The Herwood Inn
Four suites named for iconic female musicians — Carole, Aretha, Joni, Stevie.
The Hob Knob
A Gothic Revival inn on upper Main Street, nearly 100 years of hosting the Vineyard's quietest half.
The Inn at Harbor Knoll
An 1870 Dutch Colonial summer home with four rooms and serious harbor views. Proper porch.
The Millbrook Inn
A classic Dutchess County country inn, quiet and well-kept.
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.
The Reluctant Panther
A 100-plus-year-old inn at the heart of Manchester Village — the region's most serious small luxury hotel.
The Rhinecliff
An 1854 riverside building, nine balconied rooms, 170-plus years of Hudson River history.
The Six Bells
Cottagecore done right — canopy beds, antique-style wallpaper, 2025 AD Design Award.
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.
Twin Gables
Woodstock's community-minded eclectic — like staying with an artist friend.
Union Street Inn
A 1770 sea captain's home a block from Main Street. Innkeepers Ken and Deb Withrow run it themselves.
Urban Cowboy Catskills
A 19th-century Alpine Inn reborn as Nashville-in-the-Catskills. Copper tubs included.