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Greydon House

Pairing an 1850s Greek Revival home with an amazingly similar three-story addition, Greydon House offers not just 20 rooms, but a unique sense of Nantucket's identity. Calling to the site's seafaring history, the hotel has details like a pine-paneled check-in area, murals of far-off ports, and bespoke beds, all courtesy of designers Roman and Williams. The result is a space that's both perfectly matched to its surroundings and yet entirely its own, and thanks to its central location, it's also a perfect base from which to explore the rest the architectural time capsule of an area has to offer.

  • Milk Barn

    Surrounded by 15 acres of rolling hills in the Delaware River Valley, the Milk Barn is a scenic retreat just two and a half hours outside of New York City. The 1873 dairy barn has been converted into a three-bedroom home during its 30-year tranformation. Its current state retains its rustic aesthetic with etched window-doors, a massive stone fireplace, stained glass pocket doors, and the original post and beam frame, while adding modern elements like a chef's kitchen, marble bathrooms, and a projection television. Along with a guesthouse, a renovated milk shed provides additional accommodations to sleep a total of ten people. When you're not taking advantage of the outdoor swimming pool, pond, sauna, fire pits, hammocks and treehouse on the property, guests can relax inside and enjoy the home's vinyl collection on the vintage stereo system.

  • Hotel Hubertus

    Located in northern Italy and boasting outstanding views of the Dolomites and the Rieserferner Group, Hotel Hubertus is a mountainous getaway that mixes chalet-style charm with modern amenities. A range of suites, single, and double rooms are available, all of which include access to the hotel's massive park, multiple saunas and swimming pools — including the striking cantilevered Sky Pool — and fitness center. There's also an on-site spa, plenty of nearby activities like skiing and hiking, and delicious regional food available, as well as a huge selection of wines and libations to make your stay that much more relaxing.