Historic Hotels & Inns in the Catskills

Woodstock, NY · Inn

Nineteen rooms and suites plus 3 cottages on Tannery Brook Road, a short walk from Woodstock's village center. The property began as a 1940s motel and sits beside the Millstream, with gardens and hammocks along the water. Every room has a private entrance, and a continental breakfast focused on local food is included. The cottages (Brookside Bungalow, Corner Cottage and Hillcrest House) can be booked for stays of up to a month.

Tannersville, NY · Boutique Hotel

An 1890s Victorian estate on 7 acres in Tannersville, restored and reopened in fall 2022 as a 22-room hotel by Lost Boys Hospitality, with interiors by the San Francisco firm Field Theory. Original 1890s wood paneling turned up behind drywall during the renovation. The cocktail bar has a wood-burning stove, and Hunter Mountain is a short drive.

Kenoza Lake, NY · Historic Inn

A late-1800s property on 55 acres above Kenoza Lake in Sullivan County, bought by Foster Supply Hospitality in 2015 and rebuilt in 2018. It has 22 rooms and 10 standalone bungalows, with original hardwood floors, custom wallpapers and velvet furnishings. The Hemlock Spa offers Kneipp-inspired treatments, an outdoor sauna, a hot tub and a movement studio, and guests can canoe on the lake.

Shandaken, NY · Inn

Built in the late 1920s as the clubhouse for the Rip Van Winkle Golf Course, reopened in 2019 after a renovation. Fifteen rooms and 3 cottages, with La Lune and Old Hickory furniture and Phillip Jeffries wallpaper. The Esopus Creek runs along the property line. There is tennis, a pool and a fire pit, and Belleayre is nearby.

Callicoon Center, NY · Historic Resort

A resort on 23 acres in the hamlet of Callicoon Center in Sullivan County, which began as the Wenzel boarding house in 1905 and was run as a resort by the Hill family from the 1940s. It has 65 rooms, a seasonal outdoor pool, two Scandinavian saunas and a yoga deck. The Conover Club is the restaurant and bar. It is listed in the MICHELIN Guide.

Tannersville, NY · Inn

An inn on 168 acres of meadow and woodland above Tannersville, built around 1900, with 6 rooms and 4 cabins. The restaurant serves a seasonal menu every evening from chef Corwin Kave, and the bar opens in the afternoon. The inn also hosts weddings, retreats and private events. Hunter Mountain is a short drive.

Lew Beach, NY · Historic Inn

An inn on the Beaverkill River north of Livingston Manor, built in 1893 and listed on the National Register of Historic Places. It has 19 rooms, and stays include a full meal plan. Guests have direct access to the river, a trout stream long associated with the history of American fly fishing.

Round Top, NY · Inn

A 42-room inn on a 50-acre campus at 230 Winter Clove Road in Round Top, Greene County, near the waterfall it is named for. It runs arts programming alongside lodging, including residencies, workshops and events, and it hosts weddings. Artists have come to Round Top since the Hudson River School painters worked here.

Kingston, NY · Boutique Hotel

A 42-room hotel spread across four restored buildings in Kingston's historic Uptown, or Stockade, district, on Wall, Pearl, Fair and John streets. Restaurant Kinsley, at 301 Wall Street, serves a seasonal New American menu and has a wood-paneled cocktail bar, and hotel guests get a continental breakfast. Uptown's restaurants and galleries are a short walk, and the Catskills are a short drive west.

Round Top, NY · Inn

An all-inclusive resort on more than 300 acres at the base of North Mountain in Round Top, owned and run by the same family since 1838. It has 49 rooms, all meals are included, and it is open year-round. The resort describes itself as one of the oldest in upstate New York.

Windham, NY · Boutique Hotel

A hotel at 43 Route 296 in Windham, open since 1982, whose name is Italian for 'Inn of Happiness.' Rooms come in three categories, and The Cottage on Main Street is rented separately. Food and beverage service has been suspended since December 2025 while the chef is on sabbatical, so there is no breakfast or dinner on site. Windham Mountain is a short drive.

East Durham, NY · Inn

An Irish-American resort on Golden Hill Road in Cornwallville, near East Durham, owned by the Gavin family since 1961. Stays include meals: three a day in summer and five over spring and fall weekends, served as breakfast and lunch buffets and plated dinners. There is a pub with live music and an outdoor pool.

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, 8 miles from Woodstock. Seven rooms are split between the main house and a hillside cottage, including the Mobaccus suite with a 20-foot bay window over the valley. The great room has a cathedral ceiling and a stone fireplace. There is a sauna, a koi pond and trails on the grounds. It operates mainly as a wedding venue, with B&B stays on non-event weekends.

Woodstock, NY · Boutique Motel

A 1960s roadside motel about 10 minutes' drive from Woodstock village, renovated by Woodstock native Paul Covello with rooms designed by Robert and Courtney Novogratz. Its 22 rooms are named for musicians connected to Woodstock and have Crosley turntables, with records and board games to borrow from the front desk. There is a heated saltwater pool from Memorial Day to Labor Day, fire pits on the lawn, and an on-site Mexican restaurant and bar, Santa Fe Woodstock.

Stone Ridge, NY · Boutique Inn

A 1757 Dutch Colonial stone house in Stone Ridge, just under two hours from New York City, with 25 rooms across the main house, the Stable House, the Carriage House and a cottage, on 55 acres. Butterfield is the restaurant. The grounds have a cedar sauna, a cold plunge, a 100-year-old pool, a private lake and trails.

Kingston, NY · Resort

A former brickyard on 100 acres along the Hudson River in Kingston, which says its bricks went into the Empire State Building and Yankee Stadium. Guests stay in king and queen cabins, the 1873 Edgewood Mansion or a cottage. Aster, a French steakhouse, is in the mansion, the River Pavilion is open in season, and the property is open year-round. It is listed in the MICHELIN Guide.

Callicoon, NY · Historic Inn

A building from 1852 at 22 Upper Main Street in Callicoon, listed on the National Register of Historic Places and reopened in 2016 as a small inn. It has 7 rooms, a farm-to-table supper club restaurant with a mahogany bar, and Harmonie Hall, a restored second-floor ballroom used for events. The upper Delaware River runs along the edge of the village.

Margaretville, NY · Victorian Inn / B&B

A Queen Anne Victorian built in 1886 on the hill above Margaretville, listed on the National Register of Historic Places, with its original slate roof intact. There are 6 accommodations: 5 rooms and a 2-room suite. A full breakfast is served in the formal dining room on linen and English china, or on the verandah overlooking the Catskills. Belleayre Mountain is 9 miles away and Plattekill 10.