Romantic Getaways in the Catskills

Windham, NY · Boutique Hotel

Eastwind has carved out a specific lane — Scandinavian-influenced, MICHELIN Guide listed, and unambiguous about the vibe it's going for. The Lushna cabins are what most people come for: compact, considered, each with a private fire pit and separate waterfall-shower bathroom. Complimentary breakfast baskets delivered to your door every morning. The bar anchors the property in winter.

The Lushna cabins. The breakfast basket at the door every morning. The Nordic aesthetic executed with genuine commitment.

Big Indian, NY · Boutique Hotel

Eastwind's first purpose-built property and its most fully realized: 12 rooms, 9 Lushna cabins, and 6 Lushna suites on a hillside above Esopus Creek in the Oliverea Valley. Barrel saunas, communal fire pits, outdoor pool. The Dandelion Restaurant & Bar is destination dining. More remote and quieter than the Windham location — the valley views are better for it.

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.

Woodstock, NY · Boutique Hotel

A small eco-luxe hotel on Tannery Brook in Woodstock, built around a 15-foot waterfall — you can hear it from every room, and the sound carries through the whole property. Steps from Tinker Street and the village center, but the creek and tree canopy give it a more private character than the location suggests. Rooms have artist-curated turntables and vinyl collections, Bose speakers, floor-to-ceiling windows, and dedicated outdoor space. No restaurant on site, but the village's dining is a short walk. Pets not allowed. The sister property, Kingston Carriage House, is 25 minutes south if Woodstock is sold out. Listed in the MICHELIN Guide.

Tannersville, NY · Boutique Hotel

Opened Memorial Day 2024 and immediately named Best New Hotel by Architectural Digest, Condé Nast Traveler, and Esquire. Sixteen rooms in a 150-year-old property in Hensonville, renovated by owners Ely and Danielle Franko with a level of personal investment most hotels can't manufacture. Matilda — from the chefs behind Wildair and Bar Contra in NYC — is destination dining even for non-guests. Minutes from both Hunter and Windham Mountains.

Tannersville, NY · B&B

A B&B on Tannersville's main street, a short drive from Hunter Mountain's slopes. Mountain views from most rooms, breakfast included, and the kind of genuinely personal hospitality that newer design hotels in the corridor tend to advertise without delivering. The owners have been running this for years and it shows in how the place feels — a rarer thing in a corridor that's been fully discovered.

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.

Mount Tremper, NY · Boutique Inn

A 100-year-old inn on 10 private acres that somehow manages to feel like your globe-trotting uncle's country estate — Moroccan tiles, butterfly collections, sheepskin rugs by a stone fireplace, handmade wood beds. The Foxfire Bar Room is a genuine restaurant destination. Condé Nast has noticed. Eleven rooms, a private cottage, pond, lily pool, bonfire pits.

Mount Tremper, NY · Boutique Motel

Previously Kate's Lazy Meadow, completely gutted and redesigned in 2023 by owners with serious taste. Nine cabin-style suites across six Esopus Creek-front acres — rock photography, custom ceramics, craft furniture, private river access. Hammocks strung between pines. The fire pit is right on the water.

Mount Tremper, NY · Resort

A full-service spa resort in Mount Tremper with inn rooms, spa treatments, and the World's Largest Kaleidoscope on property — which is more delightful than it sounds. A well-established Catskills institution that reliably delivers on the wellness-weekend promise.

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.

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.

North Branch, NY · Inn

An owner-operated inn established in 1868 on 7 acres in North Branch, with two creeks and three buildings on the property. New ownership since 2023 brought Jake Eberle — formerly of Le Fond in Greenpoint, a Michelin-recommended Brooklyn restaurant — into the kitchen. The result is a dining room that punches above its category. Chef-prepared breakfast included with every stay.

Barryville, NY · B&B / Inn

An inn in Barryville on the upper Delaware River — the Sullivan County stretch where the water is clean and the corridor runs at its own pace. Close to Livingston Manor and the fly fishing towns to the north, but with a quieter, more river-focused character than either. The upper Delaware has a specific calm to it that the better-known Catskills towns don't offer at any price.

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.

Phoenicia, NY · Boutique Resort

Five suites on Stony Clove Creek in Phoenicia — adults-only (16+), self-serve, and intentionally unhurried. The property has a waterfront sauna positioned directly over the creek, a natural cold plunge in the creek itself, and a saltwater swimming pool. Suites range from the standalone Riverside Cottage to the two-bedroom Meadow Suite. There is no front desk and no restaurant; the design is earthy and considered without being precious about it. The sauna-to-creek sequence is the most direct version of the cold-plunge ritual anywhere in the Catskills — most properties route it through a spa menu.