Coolest Hotels in the Catskills

Several years ago, this mountainous region a little more than two hours north of New York City upped its game. Empty storefronts in all but the smallest villages transformed into farm-to-table eateries, and abandoned buildings became craft breweries and small-batch distilleries. Now, creative types escaping the hustle and bustle of the city have opened hip boutique hotels running the gamut from country chic to urban sophisticated. (And a few are just plain quirky.) Almost all are run by their owners, ensuring the hometown hospitality that has always been the calling card of the Catskills. —Mark Sullivan

A stone's throw from the Delaware River—where bald eagles are surprisingly easy to spot—is the Nest Inn. If the name is familiar, it's because owner Anna Bern runs the hip vintage furniture shop around the corner in the burgeoning community of Narrowsburg. Many of her best pieces find their way into the two guest rooms of this 1850s farmhouse, and she effortlessly mixes well-chosen antiques, midcentury treasures, and rugs found on her world travels. (She has a great eye, probably because she formerly served as design director at Vogue.) Feeling peckish? Just outside your private entrance is the Heron, a local favorite serving the region's best brunch.

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Near the top of a mountain in the community of Shandalee, The Arnold House almost single-handedly revived this sleepy part of the southern Catskills. The 10 guest rooms are delightful, with antique writing desks and quilts that preserve the country aesthetic, alongside industrial touches like metal chairs and swing-out reading lamps. A spiral staircase leads down to a tavern that specializes in line-caught trout and other regional specialties. In spring you'll find ramps—a type of wild leek with a mild garlicky flavor—in many of the dishes. On summer weekends there's barbecue and live music in the barn. For relaxation, you can book a treatment at the spa or just wander down to the pretty little pond.

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A two-lane bowling alley, uncovered when this 1868 clapboard structure was renovated in 2015, is one of the delightful discoveries at the North Branch Inn. One of the newest properties in the Catskills, it's a labor of love for the husband-and-wife team of Sims Fosterand Kirsten Harlow Foster. Tucked away in a tiny town of the same name, it has other fun finds, like a screening room with a row of seats from Radio City Music Hall and an elegantly curved bar from the 1939 World's Fair. In addition to a wood-paneled restaurant serving foods sourced from around New York State, there are five cozy guest rooms in the main building, where you'll find original woodwork and wide-plank floors. Across the street is a second building with four spacious suites where you can read in your own sitting area or soak in a claw-foot tub.

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If any lodging captures the spirit of the heyday of the Catskills, it's the Graham and Co. Recalling the summer camp atmosphere of the '50s and '60s, there are weekend bonfires, hammocks hanging under the trees, and a volleyball net (which is often transformed into an outdoor movie screen). Float in an innertube in the oval pool or grab one of the free bikes and head to the bustling main drag of the charming town of Phoenicia. Vintage maps of the area decorate the 20 guest rooms, which make great use of rough-hewn wood and shapely metal fixtures. There are no TVs in the rooms, just Tivoli radios and free Wi-Fi.

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The legendary 1969 music festival didn't really take place in Woodstock, but that doesn't stop entrepreneurs in this upscale enclave from paying homage to the event in places like the Hotel Dylan, a fun and funky lodging whose logo is emblazoned with a peace sign. The 11 generously proportioned rooms, decorated by the dynamic design duo of Cortney and Robert Novogratz from HGTV, eschew tie-dye fabrics and hemp wall hangings for a more sophisticated take on the era. There are bright pops of yellow and blue, but the prevailing color is a relaxing creamy white. It's no surprise that the place is a music lover's paradise—not only are there Crosley turntables and a supply of vinyl records in each room, there are also underwater speakers in the pool. The excellent restaurant, Santa Fe Woodstock, serves modern Mexican fare.

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The Spruceton Inn calls itself a “bed and bar,” which lets you know immediately what the vibe will be. There's a three-stool bar fashioned from wood found on the property where guests can meet each other while enjoying wine, whiskey, and cider.  (It's called Conan's Bar in homage to Arnold Schwarzenegger, a past visitor whose family once owned the place.) The property's past as a roadside motel is clearly evident, but the husband-and-wife team of Casey Scieszka and Steven Weinberg—a graphic designer and an illustrator from Brooklyn—have completely transformed the place. The nine rooms couldn't be simpler: think hand-hewn furnishings, walls dotted with tiny photos of the region, and unadorned beds covered in snowy linens.  Outside, you can play bocce or horseshoes on the lawn, cook a meal on one of the grills, or stroll along a nearby path and enjoy the mountain views.

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The century-old general store in the tiny village of Sharon Springs is now home to The Nash, one of the area's favorite destinations. But don't expect these four suites to be filled with precious heirlooms; in fact, you're more likely to find a psychedelic version of the Mona Lisa or other eye-catching works by local artists. The furnishings are sleek and modern, a nice contrast to the building's hardwood floors and elegant woodwork. Downstairs is 204 Main, a modern bistro, and you're easy walking distance from Beekman 1802 Mercantile, a shop operated by the stars of the reality show The Fabulous Beekman Boys.

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Each room at this wacky hotel is uniquely designed and decorated. You'll feel like Indiana Jones in the Archaeologist's Digs, the most recent addition to the Roxbury. Explore the three-bedroom structure and you'll find a sarcophagus, a flame-shooting idol, and a spooky cave speckled with glittering mineral deposits. There's also a delightful cocktail lounge where the seating is candy-colored cubes and a surprisingly affordable spa watched over by a golden mermaid.

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In the riverside hamlet of Barryville, this rustic retreat has just four suites in the main building and a fifth in a private cottage in the rear. One has a private balcony with a spiral staircase leading down to a hot tub, while another has a glassed-in steam shower and a cold-plunge trough tub. It's hard not to love the rain shower in another room positioned above a round metal tub big enough for two. Best of all is the two-bedroom cabin, which calls to mind the region's kitschy motels with a Formica dinette set, cabinets covered with paint-by-numbers art, and an Elvis Presley lamp. The location is an easy stroll from half a dozen eateries, including the famed River Market.

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The steeple on this inn makes it look like a tiny church, but this 19th-century whitewashed structure in the community of Barryville did indeed serve as a one-room schoolhouse for more than 50 years. In case you need evidence, glance over at the chalkboard or schoolhouse lights dangling from the 16-foot ceilings in the expansive lobby. Owner Bronson Bigelow has transformed the Hillside School into two spacious suites—the Belfry and Room 1893. Set beneath the eaves, the Belfry includes the bell tower, which has been glassed in to give you a view of the cast-iron bell, while Room 1893 has a sunny skylight and handmade furnishings fashioned from items salvaged during the renovation process.

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