Historic Hotels & Inns in the Catskills
The Catskills have been a resort destination since the mid-1800s, when steamships brought New Yorkers up the Hudson and horse-drawn carriages delivered them to sprawling wooden hotels. Most of those hotels are gone. What's left is a more scattered inheritance: converted manor houses, Victorian inns, a few properties that have operated continuously since before the First World War. Beaverkill Valley Inn has been fishing-focused since 1895. The region's oldest properties have a weight to them that no amount of renovation can replicate.
20 Properties
The Woodstock Inn on the Millstream
Woodstock, NY · Inn
Don't let the modest exterior fool you. The Woodstock Inn on the Millstream earns its reputation through consistency — clean, well-run, and genuinely situated within walking distance of everything Woodstock has to offer. The creek running alongside the property is a legitimate selling point, especially in summer. Not flashy, not trying to be. Just a good inn in a good town.
The Kaaterskill
Tannersville, NY · Boutique Hotel
Tannersville's 'painted ladies' Victorian strip is one of the more unexpected sights in the Catskills, and The Kaaterskill sits right in the middle of it. The hotel has real history in a town with real history, and the current version balances that heritage with the kind of comfort modern travelers expect. Hunter Mountain is a short drive. The main street is walkable. A genuine mountain town hotel, which is rarer than it sounds.
Hotel Lilien
Tannersville, NY · Boutique Hotel
A Victorian mansion on Route 23A since the 1890s — original woodwork, stained glass intact. Twenty-two rooms, a bar with a jukebox that's become the actual living room of Tannersville, a billiards room, and a library left deliberately untouched. Hunter Mountain is minutes away. Kaaterskill Falls is eight minutes. In winter, they put out a sled menu.
Kenoza Hall
Kenoza Lake, NY · Historic Inn
A late-1800s property on 55 acres overlooking Kenoza Lake, operated by Foster Supply Hospitality. Twenty-two rooms plus ten standalone bungalow accommodations, original hardwood floors, custom wallpapers, and velvet furnishings. The Hemlock Spa offers Kneipp-inspired treatments with an outdoor sauna, hot tub, and movement studio. Canoeing on the lake. The restaurant's lakeside terrace fills up on weekends.
Shandaken Inn
Shandaken, NY · Inn
Built in the late 1920s as the clubhouse for the Rip Van Winkle Golf Course, reopened in 2019 after a careful renovation. Fifteen rooms and three cottages with La Lune and Old Hickory furniture, Phillip Jeffries wallpaper. The Esopus Creek runs along the property line. Tennis, pool, fire pit, Belleayre nearby.
Callicoon Hills
Callicoon Center, NY · Historic Resort
A 120-year-old property on 23 acres in Sullivan County, operating since 1905. Sixty-five rooms, an oversized pool, yoga deck, saunas, The Conover Club restaurant. The spirit deliberately points at Borscht Belt communal energy — people come here to gather. Sullivan County's resurgent food and arts scene is all around it.
Deer Mountain Inn
Tannersville, NY · Inn
Six rooms and four standalone cabins on 168 wooded acres above Tannersville. Turn-of-the-century construction that has stopped trying to prove anything. The dining is what brings people back — full meals, local sourcing, the kind of table you sit at longer than planned. Hunter Mountain is a short drive.
Beaverkill Valley Inn
Lew Beach, NY · Historic Inn
Built in 1893 and on the National Historic Register, one of the oldest continuously operated inns in the Catskills. Nineteen rooms, full meal plan, and direct access to the Beaverkill River — the most historically significant trout stream in American fly fishing. Not a design hotel. A place doing the same right thing for 130 years.
Glen Falls House
Round Top, NY · Inn
A historic inn in Round Top — one of the more genuinely beautiful and undervisited corners of Greene County — near its namesake waterfall. Arts programming runs alongside lodging: residencies, workshops, events. Round Top has drawn artists since the Hudson River School painters found the light here. That quality persists.
Hotel Kinsley
Kingston, NY · Boutique Hotel
Several restored historic buildings in uptown Kingston — a launching pad as much as a destination. Kingston has become genuinely interesting: good restaurants, galleries, record stores, a food scene that doesn't perform for tourists. The hotel anchors the neighborhood without overwhelming it. Catskills access is a short drive west.
Winter Clove Inn
Round Top, NY · Inn
One of the oldest continuously operating inns in the Catskills — family-run since 1830 and still going. Full meal plan, golf, skiing, hiking, and events on property. Not a boutique play, but genuinely historic and an important piece of what the Catskills has always been.
Albergo Allegria Hotel
Windham, NY · Boutique Hotel
A family-run boutique hotel in Windham with charming rooms and an excellent breakfast that guests talk about more than the rooms. Antique-accented aesthetic and warmth that the larger properties can't manufacture. The kind of find you feel like you discovered even though it's been here for decades.
Gavin's Irish Country Inn
East Durham, NY · Inn
The anchor of East Durham's Irish Catskills community — an inn and pub with live music seven nights a week, Irish hospitality, and a setting that exists entirely apart from the boutique corridor. East Durham has been the center of Irish-American summer culture in the Catskills for generations. A piece of regional history that the broader Catskills conversation tends to undercount.
Onteora, The Mountain House
Boiceville, NY · Boutique Inn / B&B
Built in 1928 as the summer estate of Richard Hellmann — of Hellmann's mayonnaise — on 200 acres on Mount Tycetonik, eight miles from Woodstock. Seven rooms split between the main house and a hillside cottage, including the Mobaccus suite with its 20-foot bay window overlooking the valley. The great room — cathedral ceiling, stone fireplace, large picture window — frames the panoramic mountain view that was the original selling point and still is. Sauna, koi pond, and trails on the grounds. Primarily a wedding venue now, which means B&B guests get the run of a grand estate on non-event weekends. The Catskills have always attracted exactly this kind of New York money.
Hotel Dylan
Woodstock, NY · Boutique Motel
A bohemian-styled motel on Maverick Road named for the obvious and delivering on the premise — close to Woodstock's arts scene, studios, and hiking, with a rock-and-roll aesthetic that doesn't take itself too seriously. Comfortable, affordable, and genuinely Woodstock.
Hasbrouck House
Stone Ridge, NY · Boutique Inn
An 18th-century Dutch Colonial stone mansion in Stone Ridge converted into a boutique property — 20+ suites across the main house, carriage house, and stable. Restaurant Butterfield on site. Heated bathroom floors, outdoor sauna, game room.
Hutton Brickyards
Kingston, NY · Resort
A decommissioned 19th-century brickyard on the Hudson River reconceived as a luxury retreat with waterfront cabins and the restored Edgewood Mansion. Two restaurants, spa, 100 riverfront acres. Travel+Leisure–recognized.
The Western Supper Club & Inn
Callicoon, NY · Historic Inn
A Victorian building from 1852 on Upper Main Street in Callicoon, listed on the National Register of Historic Places. Seven rooms, a farm-to-table supper club restaurant, and Harmonie Hall — a second-floor ballroom used for events. Reopened in 2016 as a boutique inn. Upper Delaware River country, Sullivan County side.
Margaretville Mountain Inn
Margaretville, NY · Victorian Inn / B&B
A Queen Anne Victorian built in 1886 on the hill above Margaretville, on the National Register of Historic Places, with the original slate roof intact. Six rooms and a two-room suite, each with a private bath. Breakfast is served formally in the dining room on linen and English china, or on the verandah overlooking the Catskills — one of the better included breakfasts in the region. There is also a spa in the milk house of a circa-1910 Sears Roebuck barn on the property. Belleayre Mountain is nine miles away; Plattekill is ten. The most architecturally significant B&B in the Delaware County corridor.
Dry Town Tavern
Andes, NY · Inn / Tavern
Five rooms connected to a well-regarded tavern in Andes — old school charm with modern amenities, and a personality that feels genuinely Western Catskills rather than curated for visitors.
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Browse Now →What Makes It
- •The Sullivan County properties tend to hold the most genuine history — the Delaware River valley was a destination for Philadelphia money as well as New York, and the old estates reflect that. The Ulster County corridor is younger and more recent in its redevelopment.
- •Several historic properties sit directly on or adjacent to protected trout streams — the Catskill fly-fishing tradition and the grand hotel tradition developed together. Beaverkill Valley Inn is the clearest expression of this overlap.
- •The best historic Catskills properties have been updated without erasing what they are — original wide-plank floors, stone fireplaces, and the bones of buildings that weren't built to be temporary. The age shows, and that's the point.
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