This Is One of the Mid-Atlantic Region’s Most Prestigious Boutique Hotel

The unmistakable, undeniable charm of the Inn at Perry Cabin begins from the moment you turn onto its long driveway. As you make your way up the gravel road, the amenities of the 26-acre resort begin to beckon; on your left, you’ll find the Inn’s spa and pool, croquet field, and bocce ball court. You’ll find three clay tennis courts behind manicured greenery on your right. Make no mistake, the Inn at Perry Cabin is a resort where relaxation and rejuvenation are key. But with this boutique hotel’s opportunities, you’ll want to play hard before falling into bed each night. 

Perhaps one of the best-known luxury resorts of the Mid-Atlantic region, this intimate hotel, which traces its roots to a colonial farmhouse built in 1812, pays homage to the nautical history of St. Michaels while bringing forth modern luxury and southern hospitality. With stunning vistas of the Miles River, the Inn is the perfect backdrop to classic celebrations of Americana. Of course, the directors of the 2005 film Wedding Crashers had the same idea when they chose the Inn as their set location for its opening wedding scene. 

While the movie may have been fiction, there’s no fibbing about the fun at the Inn, whether on land or sea. In addition to a room key, guests are presented with a brochure of daily events at check-in. Perhaps most time-honored is the nightly 5 p.m. toast that calls guests to the riverside to raise a glass to the Inn’s time-honored flag, Don’t Give Up the Ship (a famous battle cry during the War of 1812). Other activities include glass etching, cookie decorating, bike tours of historic St. Michaels, and kayak and paddleboarding tours on the river. 

For the nautically inclined, it simply wouldn’t be a visit to the Eastern Shore without spending some serious time on the water. To oblige, the Inn has its fleet of sailboats and yachts, including “Five Star,” a 55’ Hinckley yacht offering a 90-minute tour of the scenic river and associated wildlife. And if you’re looking to upgrade your sailing skills, the ASA-accredited Sailing Academy offers basic through multi-day sailing certification courses. 

If traipsing about the Chesapeake isn’t your thing, you’ll want to head to the Inn’s renowned golf course designed by Pete Dye, the Links at Perry Cabin. This 18-hole championship golf course is the Maryland shore at its finest, featuring majestic trees, bunkers, and distinctive water features, with a finishing stretch overlooking the Chesapeake Bay. Tennis lovers will also find three har-tru clay courts lit for play at dusk or dawn. 

With so much to do, it’s easy to forget that the Inn is also second to none in offering a relaxing escape from urbanity. Guest rooms still feature the colonial mansion’s original architectural details, with antique dressers, French door verandas, overstuffed couches, and modern touches like soaring ceilings and in-room coffee machines. The luxury of the Inn is casual and understated rather than fussy, calling to guests to put their feet up for a change. Of course, there’s no better place for some R&R than at the Inn’s spa, featuring seven stunning treatment rooms. 

St. Michaels has no shortage of food and drink options in its postage stamp-sized city limits, but there’s plenty to eat and drink on the Inn’s premises, starting with fine dining destination STARS. The elegant waterfront restaurant features a constantly changing menu of fresh, seasonal produce, locally-raised meats and poultry, and the day’s catch from the surrounding waters. Everything from duck dumplings to a classic crab cake is on the menu. If you’re looking for more of a light bite, head over to Purser’s Pub, a more casual locale where you might imagine a few sailors gathering.

Credit: Nicole Sunderland

Whether staying for two nights or two weeks, the multiplicity of opportunities makes time move too quickly at the Inn at Perry Cabin. Thankfully, just two hours away from Washington, D.C., getting back to the Inn is as convenient as necessary. 

Top Takeaways

Location: St Michaels, Maryland 

Rating: Five-Star

The Vibe: Nautical Americana combining colonial elegance with modern luxury 

Food + Drink: Check out STARS for fine dining (and breakfast) and the Pursers Pub for a cocktail. There’s also poolside dining during warmer months. 

Amenities: Spa; Fitness center; Swimming pool; Restaurant; Bar; Concierge; Bocce; Croquet, Tennis courts; Golf course  

Our Favorite Thing About the Hotel: The view of the river is simply second to none – be sure to grab a meal outside. 

5 Nearby Attractions: Easton town center, Audubon Center, Tilghman Island, Assateague Island, colonial Cambridge 

Any Personal Neighborhood Recs?: One of the best restaurants in St. Michaels and Maryland can be found just down the street at Ruse in the Wildest Hotel

Rooms: 30 suites and 48 guest rooms

Pricing: Rooms start at $460/night  

Closest Airport: BWI Airport 

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