Inn at Perry Cabin, Maryland

Few arrivals set the tone for a getaway quite like pulling up to what feels like your own stately home on the Chesapeake Bay. At Inn at Perry Cabin, luxury takes on the tried-and-true character of the elegant Eastern Shore: manicured gardens, fresh seafood, days in and around the water, and the intrigue and ease of historic St. Michaels.

The inn has a strong nautical heritage (it was founded in 1819 by a locally revered Navy man and seafarer) and maintains its own fleet of boats, making sailing one of its signature experiences. Guests can book everything from hands-on sailing lessons to private sunset charters or rum-tasting excursions on the Miles River.

Back on land, guests can book a round of golf, borrow a bicycle to explore town, retreat to the spa, or linger over dinner in private boathouses along the Miles River.

Chatham Bars Inn, Massachusetts

For more than a century, the five-star Chatham Bars Inn (founded in 1914!) has occupied an enviable perch overlooking the Atlantic. Today, the oceanfront resort on Cape Cod blends classic New England elegance with amenities that tempt you to stay put.

Its spa includes an adults-only outdoor pool, heated deck, hot tub, private cabanas, and even a Japanese Zen garden, while the seaside setting opens the door to quintessential Cape experiences. Add fresh coastal cuisine, turn-of-the-century charm, a resort-owned fleet of boats, and even Lexus shuttle service and test drives and the result feels like a modern take on the classic grand American seaside resort.

Mountain Shadows, Arizona

In Paradise Valley, luxury takes on a decidedly modern feel. One of the top resorts in the American Southwest, Mountain Shadows pairs striking architecture and contemporary design with a natural amenity no other hotel can match: a dramatic desert landscape with famed Camelback Mountain looming nearby.

The setting makes a compelling case for slowing down and staying outside, whether that means lounging poolside, teeing off on the resort’s short course, or simply watching the desert change color as the sun goes down. (Hit the sunset pool for the full experience.) It’s sleek, sophisticated, and unmistakably Southwestern, so guests are treated to a true change of pace.

Costa d’Este Beach Resort & Spa, Florida

Florida luxury doesn’t have to mean velvet ropes and see-and-be-seen beaches. In laid-back Vero Beach on the eastern coast of Florida, Costa d’Este Beach Resort & Spa—owned by none other than Emilio and Gloria Estefan—offers an intimate take on oceanfront glamour. Dress up your flip-flops but don’t get too fussy: here, luxury is organic and breezy, not showy.

Wake for sunrise over the Atlantic, join morning yoga on the beach, spend the afternoon next to the oceanfront infinity pool, or book a treatment at the spa. Whatever you choose, you’ll find that here, the experience is all about simple pleasures done well.

What’s more, guests get bits of authentic culture without having to leave the country or venture down to the Magic City: Miami-Cuban influences pop up throughout the resort, from the design to the dining (paella at The Wave or Cuban coffee at the cabana bar, anyone?), giving this beachfront escape a unique personality in the world of luxury beach resorts.

Explore more destinations across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.