The Best Boutique Hotels in Upstate New York & Hudson Valley

July 7, 2022

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.

Troutbeck
Troutbeck

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.

Hutton Brickyards

As New Yorkers rediscover the charms of local travel, places like the Hudson Valley are not just booming, but blooming, with stunning destinations sprouting from the unlikeliest sources. Hutton Brickyards, in Kingston, 90 miles up the river from Manhattan, is one of these: a decommissioned industrial site finding new life as a stylish and luxurious retreat, a combination of a modern boutique hotel and a multi-purpose event venue.

Hutton Brickyards
Hutton Brickyards

The old kiln sheds and crane still stand proudly on the 73-acre site, joined now by modern cabins and low-slung, brick-based buildings housing the hotel’s common spaces. The interiors are clean-lined but never cold, thanks to their Shaker-inspired furnishings and richly textured hardwood floors and ceilings.

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.

Eastwind - Hotel & Bar
Eastwind - Hotel & Bar

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
The Roxbury

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 Roundhouse
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.

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

Popular Questions

Which of the best upstate New York boutique hotels in the Hudson Valley or the Catskills are accessible by train?

If you’re on the lookout for an escape from New York City that doesn’t require a rental car, the following boutique hotels in upstate New York are accessible by Amtrak or Metro North (some will require a short car service from the train station). You can always contact our Travel Specialists for assistance planning specific routes.
Troutbeck
The Roundhouse
The Amelia Hudson
Hutton Brickyards
Twin Gables of Woodstock

Which of the best upstate New York boutique hotels in the Hudson Valley or the Catskills allow pets?

For anyone with a pet by their side, you have plenty of choices among the best upstate New York boutique hotels in the Hudson Valley or the Catskills. Here’s a sample of those that welcome pets (charges and certain restrictions may apply):
Eastwind Hotel & Bar
Troutbeck
The Wick, Hudson
Hutton Brickyards
Callicoon Hills
Woodstock Way Hotel

Which of the best upstate New York boutique hotels in the Hudson Valley or the Catskills are located nearby a cute or walkable town?

Upstate New York is known for its small, charming towns — often featuring a main street of shops and restaurants. Here are a few of the best upstate New York boutique hotels that offer easy access to a classic upstate town:
The Roundhouse
The Wick, Hudson
The Amelia, Hudson

Which of the best upstate New York boutique hotels in the Hudson Valley or the Catskills have a spa?

Several of the best upstate New York boutique hotels in the Hudson Valley or the Catskills feature a spa
The Roxbury
The Roxbury at Stratton Falls
Hutton Brickyards

Which of the best upstate New York boutique hotels in the Hudson Valley or the Catskills have a pool?

Several of the best upstate New York boutique hotels in the Hudson Valley or the Catskills feature a pool:
The Roxbury
The Roxbury at Stratton Falls
Callicoon Hills
Troutbeck
The Amelia, Hudson