The Best Boutique Hotels in Upstate New York & Hudson Valley

December 15, 2023

Tablet Hotels is your source for discovering the world’s most exciting boutique hotels — places where you’ll find a memorable experience, not just a room for the night. For over twenty years we’ve scoured the earth, evaluating hotels for every taste and budget, creating a hand-picked selection that’s proven and unforgettable. Now, we’re the official hotel selection of the legendary MICHELIN Guide. Here are the best boutique hotels in Upstate New York & Hudson Valley.

Troutbeck

Troutbeck didn’t just wake up one morning and decide to style itself a creative retreat — it’s been walking the walk for well over a century, having welcomed Mark Twain, Ralph Waldo Emerson, and Henry David Thoreau, and many others along the way. And while this estate, in Amenia, two hours from Manhattan, has seen some changes over the years — the Century Lodge dates back to 1760, while the Manor House was added in 1919 — it’s perhaps most remarkable for its continuity.

Rather than let the place become a museum piece, the new owners opted for a very thorough renovation. But it’s the rare renovation that preserves the historical character while bringing the experience entirely up to date. It’s a fine line to walk, but this is a talented team — its husband-and-wife owners brought in the mother of the groom, Alexandra Champalimaud, to handle the design work, and the result is a hospitality masterpiece.

Hotel Lilien

The new wave of Catskills hospitality is less about resorts and more about boutique-scale hotels — in the case of Hotel Lilien, an 1890s Victorian mansion and estate in Tannersville, New York that’s been transformed into an 18-room boutique hotel. It’s the work of the Lost Boys Hospitality Group, in collaboration with the San Francisco–based designers Field Theory, but there’s nothing overtly Californian — or Victorian, for that matter — about the design. Instead, it’s an eclectic survey of multiple styles and eras, including classic 20th-century modernist design pieces and a constantly churning collection of artworks by contemporary New York artists.

Its rooms, naturally, are all different; some are original, others later additions, but all share the Lilien’s warm, organic style. There’s no TV in the rooms, and that’s a conscious choice; guests are invited to socialize over a plated European breakfast accompanied by impeccably sourced pastries and coffee, and in a bar and lounge that serves a full dinner menu alongside a well-chosen selection of wines, local beers, and seasonal cocktails. Meanwhile the outdoor offerings include a swimming pool and a fire pit, as well as hiking at Kaaterskill Falls, mere minutes away.

Eastwind - Hotel & Bar

With outdoor recreation more popular than ever, we knew the Catskills, just a two-hour drive from New York City, couldn’t stay unfashionable forever. But it’s a bit surprising just how quickly a place that hasn’t been hip since our grandparents were kids has managed to reinvent itself. Eastwind Hotel & Bar, in the town of Windham, is a case in point. It’s co-owned by a German/Lithuanian couple who saw a bit of his own childhood in the landscapes and lodges of upstate New York, and who redesigned this 1920s-era lodge (and its outlying A-frame cabins) with an eye toward Scandinavian modernist style.

The result is a sort of high-design summer-camp vibe, with more than a touch of luxury — vintage furniture and Frette linens happily cohabitate here. It’s a refreshingly unique vision, one that avoids the off-the-rack details of some superficially similar hotels. The rooms, suites, and studios are joined by seven pod-like cabins, which sacrifice some square footage for a more complete sense of immersion in nature. As stylish as Eastwind is, the atmosphere remains decidedly casual. And thanks to its modest size, the hotel’s public spaces never feel crowded, though they’re busy enough to feel appealingly social.

The Roxbury

When we were young the Catskills were where our grandparents vacationed. But now, with flying growing more dehumanizing by the year, car-trip holidays are back in style. And it can’t be a coincidence that hip country hotels like the Roxbury are opening in unlikely places — this one in the town of the same name, just under three hours from New York City, a few miles to the north and west of the famous town of Woodstock.

The Roxbury breaks the mold a bit — the colonial house might put you in mind of a bed and breakfast, and the adjoining motel building is a low-profile pre-modernist classic. Rooms, however, are anything but traditional, with design themes that range from the vibrant and contemporary to the flamboyantly retro. The idea here, clearly, is not minimalism but a sort of maximalism, throwing the usual boutique clichés out the window. Plenty of hotels call themselves “playful,” but few have anything that even begins to approach something like the Roxbury’s Archeologist’s Digs suite, with its secret passageways, its Mayan Temple–inspired bedroom, its fish swimming in a saltwater aquarium alongside the glass-walled shower, and more than a few details that are simply beyond description. (Can’t find the bed? Try pulling the life-size Mayan idol’s nose ring and all will be revealed….)

The Roundhouse

Beacon is one of a few formerly depressed post-industrial towns along the Hudson that are making a bit of a comeback, as New Yorkers increasingly head upstate for a break from city life. Thanks in large part to the Dia Art Foundation, who chose Beacon as the setting for their impressive contemporary art museum, it’s one place where you can get a contemporary cultural fix along with some much-needed fresh air. And it’s this combination of pastoral charm and contemporary arts and design heritage that’s perfectly encapsulated by the Roundhouse.

The hotel is made from the bones of an old mill, perched on the banks of Fishkill Creek, and the sound of a small waterfall provides a suitably bucolic soundtrack. A very thorough renovation at the hands of the Rockwell Group has transformed it into the very picture of the modern post-industrial luxury hotel, where sleek mid-century furniture sits under exposed concrete ceilings. Spacious showers and, in some cases, freestanding tubs add a touch of spa-like luxury, and Keurig coffee machines ensure that New Yorkers’ caffeine levels remain within a safely tolerable range.

Little Cat Lodge

The Hudson Valley’s Little Cat Lodge is named not for a specific little cat, but for Catamount Mountain, in whose shadow the town of Hillsdale, New York stands. This is a properly rural escape, make no mistake — but it’s also within driving distance of both Boston and New York City, and attracts urban travelers with the promise of well-considered retro-Alpine style as well as a restaurant conceived by its hosts, who are also award-winning restaurateurs.

Little Cat Lodge’s rooms and suites have been thoroughly updated, though they’re dressed in a throwback style that’s true to the ski culture of upstate New York and western Massachusetts, and influenced by classic European chalets as well. The custom-made beds were crafted from local wood, and the comforts, though short of luxury-resort territory, are more than up to the challenge of restoring tired skiers. Meanwhile the lodge’s public spaces are surprisingly substantial: the hotel’s dining room opens onto an expansive covered terrace, and the tavern combines a bar and a casual restaurant under a single roof.

Seminary Hill Orchard & Cidery

It’s been fifty years or more since the Catskills were so popular a destination, and the hotel scene, correspondingly, is booming. Seminary Hill Orchard & Cidery, on the outskirts of Callicoon, New York, has drawn attention for its modern cidery structure, which takes the traditional barn-style silhouette in a modern and extremely sustainable direction. Just down the road, however, in a pair of houses renovated by local hospitality experts Homestedt, is what brings us to Seminary Hill: the Boarding House, a 17-room boutique hotel in a Shaker-inspired contemporary-classic style.

The end result is a lodging that’s perfect for today’s Catskills: rustic and restful without being overtly retro, and certainly not kitschy. At the same time, as photogenic as it may be, it’s a place with thoughtful comforts, made to appeal to more senses than just the visual. The Boarding House name suits the concept; the vibe is low-maintenance and self-sufficient, with kitchenettes in each room and a communal breakfast served in the parlour kitchen. Meanwhile, in the cidery building, there’s a tasting room, as well as a proper restaurant serving lunch and dinner with an expansive view of the landscape.

The Starlite Motel

With road trips and local travel on the rise, the Catskills, with their plentiful supply of mid-century hotels, motels, and resorts, are enjoying a second life. And while plenty of modern-day Catskills hoteliers are embracing the region’s hospitality history, few are quite as unashamedly retro as Kerhonkson’s beautifully restored Starlite Motel.

The exterior color palette, with its pinks, aquas, and mint greens, is straight out of the 1960s, as is the giant MOTEL sign that adorns the rooftop of this low-slung structure. The interiors, however, take things in a more contemporary direction — the Starlite’s proprietors are veterans of New York’s art, fashion, and design worlds, and created their own visual language for the rooms, which feel lighter, brighter, and more polished than the hotel’s mid-century inspiration might suggest.

Urban Cowboy Lodge

More cowboy than urban, frankly; the first thing that strikes you about Urban Cowboy Catskills is that the rustic vibe, rather than being replaced with hard-edged minimalism or Scandinavian modernism, has been left intact, or even heightened. Sure, it’s a contemporary, carefully curated, and very self-aware sort of rustic, but it’s all the more likeable for it; why go to the trouble of leaving the city if the city just follows you around?

There are exceptions. A walk-in rain shower or a Japanese cedar bathtub take liberties with the style, but it’s worth it in the name of comfort. Urban Cowboy’s 28 rooms and suites are divided across five separate buildings, and they range in size from the generous cabin-style rooms in Walden to the vast six-bedroom suite that occupies the second floor of the Lodge. They’re all cozy, and not in the way that actually means “small” — with Pendleton blankets and décor that leans heavily on wood and leather, they feel warm and thoroughly welcoming.

The Amelia Hudson

The most successful boutique hotels make the most of the raw material they’re given — in the case of the Amelia Hotel, in the small upstate city of Hudson, that’s a 19th-century Queen Anne–style house on a quiet residential street a short walk from Warren Street, the town’s main drag. It’s undergone a thorough but very sensitive renovation, and has been updated with modern furniture and quietly chic design pieces, as well as pieces by some big names in modern and contemporary art. The result is an experience that’s luxurious but unpretentiously so — details like Matouk linens, Frette towels, and Nespresso machines are welcome comforts but far from ostentatious.

There are exceptions. A walk-in rain shower or a Japanese cedar bathtub take liberties with the style, but it’s worth it in the name of comfort. Urban Cowboy’s 28 rooms and suites are divided across five separate buildings, and they range in size from the generous cabin-style rooms in Walden to the vast six-bedroom suite that occupies the second floor of the Lodge. They’re all cozy, and not in the way that actually means “small” — with Pendleton blankets and décor that leans heavily on wood and leather, they feel warm and thoroughly welcoming.

More boutique hotel lists in the New York Area:

New York Boutique Hotels
Brooklyn Boutique Hotels
Greenwich Village Boutique Hotels
Soho New York Village Boutique Hotels
Tribeca & Wall St Boutique Hotels
Meatpacking NYC Boutique Hotels
Flatiron NYC Boutique Hotels
Long Island New York Boutique Hotels

View our entire selection of Boutique Hotels in New York

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