Inn at Perry Cabin- St. Michaels, MD

Nestled on the shores of the Chesapeake Bay, there is no doubt the Inn at Perry Cabin is situated on one stunning piece of waterfront property. Even in the winter, the grounds are breathtaking. However, even the majestic oaks seem to be counting the days until summer arrives; this is one historic hotel best experienced in warmer weather.

Original Structure Inn at Perry Cabin — Original Structure

Built in 1816 on one of England’s original land grants, the Inn was designed by Commodore Oliver Hazard Perry’s aide-de-camp Samuel Hambleton, the Navy’s first Purser and War of 1812 veteran, to resemble Perry’s cabin on the the flagship USS Niagara. Which neatly explains the somewhat odd name. Following Hambleton’s death, the property was first used as a working tobacco farm, then later as a riding academy, which operated at the site until 1980.

In 1980, the Greek Revival manor along with 25 acres was purchased by the Meyerhoff’s, owners of 1979’s Kentucky Derby winner Spectacular Bid, which I am assuming was also required to land this magnificent property. They quickly converted Hambleton’s home to a six bedroom inn and restaurant, the genesis of today’s much larger property. After a decade the property was purchased by 80’s textile magnate Sir Bernard Ashley, of Laura Ashley fame. The Inn, along with other Ashley House properties, including Charlottesville’s Keswick Hall, would showcase his extensive antique collection, as well as offer the experience of staying at a luxurious English manor house. Following a two year restoration and expansion, the Inn at Perry Cabin reopened as a 41 room luxury hotel.

Following Ashley’s death in 2009, the Inn was acquired by the luxury hotel group Orient-Express, who spent $17 million to update and expand the property. The room count doubled, amenities were added, and the property quickly became known for luxurious summer getaways, as well as a popular wedding venue. So much so, it even appeared in the movie Wedding Crashers.

There is no denying the renovations were masterfully done, and the original portion of the hotel retains the charm of the colonial building. The common areas are wonderfully decorated, and impossibly cozy. There are all manner of rooms to explore, which will delight anyone who enjoys historic properties. The onsite restaurant has an amazing view of the water, and during the summer, all sorts of outside activities are offered. Naturally, it has an amazing pool. It was even designated as the best hotel in Maryland by Travel + Leisure. I am not sure I would agree with that, but would definitely place it on the short list. For me, a bit of the charm was lost with the addition of the new buildings, and then there is the astronomical cost. Obscenely astronomical. I found it nice, but not nice enough to justify the price tag. In all honesty however, my view may be colored by my off-season visit. Which incidentally was still ridiculously expensive, but lacked the garden and all the outdoor activities available in the summer.

Located in the main building, our standard room was again nice enough, but not really remarkable. It was pleasantly decorated, and the bedding was comfortable. It was a good size, and came with a small patio, which we did not use as it was freezing. We really enjoyed both restaurants, and the property is just a short walk to town, which is full of shops, historic houses and waterfront restaurants. I am not sure I would return, given the price, but it is a lovely historic property, and worth a visit, if only to the restaurant.