Inn at Perry Cabin & Links at Perry Cabin

A Pete Dye Mulligan — and Sailing in Style on Maryland’s Eastern Shore

Pete Dye’s final design ends with a dramatic three-hole stretch known as the “Goodnight Kiss.” [credit: Inn at Perry Cabin]

It starts with a reserved parking space—not at the inn, but at a marina just outside of Annapolis.

On a typical Friday afternoon in season, a single party of guests pulls into Pier 7 Resort Marina in Edgewater, Maryland, checks in, and steps aboard a 55-foot Hinckley Talaria yacht bound for the Eastern Shore. Varnished teak, an unmistakably New England profile, champagne, and charcuterie make the journey feel very different from sitting in bridge traffic with everyone else heading east for the weekend. By the time the Hinckley reaches the Miles River, the boat ride included in the Inn at Perry Cabin’s Skip the Bridge package has already become part of the getaway rather than something to recover from.

About ninety minutes after departure, the Five Star docks at the Inn at Perry Cabin, at the edge of the harbor town of St. Michaels. As the party of up to six disembarks, the captain leads them inside for a VIP check-in. Most guests still arrive the conventional way, by car, though it wasn't always so: arrival by water was once the norm here, long before Route 33 made the drive from Washington or Baltimore an easy one. No matter the mode of arrival, many guests take to the water anyway once they've settled in—sailing excursions depart from the marina, classic boats come and go throughout the day, and the river remains a lively focal point.

St. Michaels itself adds to the appeal—a walkable Chesapeake town of galleries, seafood spots, a small distillery, and a local winery. Fans of the 2005 comedy Wedding Crashers may recognize the inn’s waterfront lawn from the film’s wedding scenes, though in person the setting feels less like a movie backdrop and more like a place that has quietly hosted weekends like this for generations.

The Inn at Perry Cabin stretches along the Miles River, where water shapes the experience. [credit: Inn at Perry Cabin]

For golfers, there’s another reason the destination has gained attention. Just a mile or so down the road sits the Links at Perry Cabin, widely regarded as the final course Pete Dye personally completed. Available to inn guests, members, and their guests, it plays with the atmosphere of a private club—well groomed, uncrowded, and comfortable to walk, and in step with the ambiance of the Inn itself.

Together, the town, the water, and Dye’s final design give Perry Cabin a personality that’s unusual among East Coast golf getaways: equal parts sailing weekend, small-town escape, and true golf trip.

From Private Waterfront Home to Golf Destination

Inn at Perry Cabin's waterfront lawn appeared in the 2005 comedy *Wedding Crashers*. [credit: Inn at Perry Cabin]

Long before Perry Cabin became a resort, the property was a waterfront home overlooking a busy Chesapeake harbor. Built in the early nineteenth century, it stood within a working maritime town shaped by shipbuilding, oyster harvesting, and coastal trade. The river was livelihood first, scenery second—a practical relationship that still explains why the inn feels so naturally tied to the water today.

For generations the estate remained private, evolving alongside St. Michaels as the town gradually shifted from commercial port to weekend escape. By 1980 the house had begun operating as a small-scale inn, but its modern identity took shape after British entrepreneur Sir Bernard Ashley—husband of designer Laura Ashley—acquired the property in 1989.

Ashley expanded and refined the inn while preserving its residential scale, establishing a character that endures today—English garden sensibility layered onto Chesapeake nautical tradition. The design emphasizes arrival by boat as much as by road. The aim was not to create a large resort, but a place that felt like a well-kept private estate that happened to welcome guests.

Perry Cabin later became part of Orient-Express Hotels, the luxury hospitality group that rebranded as Belmond—a period that elevated service standards while cementing its reputation as one of the East Coast’s most distinctive waterfront retreats. Today the inn operates within Preferred Hotels & Resorts’ Legend Collection, continuing a pattern of gradual evolution rather than reinvention.

The water has remained central throughout. Perry Cabin maintains an unusually active fleet, from Hinckley yachts and sailing vessels to one of the Chesapeake Bay’s surviving historic skipjacks, the Stanley Norman, built in 1902. Seasonal sails and oyster-dredging demonstrations connect guests directly to the working traditions that once powered the region’s economy, reinforcing that the inn’s maritime identity is lived rather than decorative.

The 1902 *Stanley Norman* carries Chesapeake history aboard one of its surviving skipjacks. [credit: Inn at Perry Cabin]

Golf became part of the Perry Cabin story only recently—and very intentionally.

When investor Richard Cohen’s Capital Properties acquired the Inn at Perry Cabin in 2014, it offered sailing, gardens, and an established reputation as one of the Eastern Shore’s classic inns. What it didn’t have was dedicated golf or racquet sports. Cohen’s vision was to expand the inn into a full resort experience, adding championship golf, racquet facilities, and related amenities within easy reach of guests.

To add golf, his company purchased the nearby Harbourtowne Golf Resort and Conference Center, including the existing Harbourtowne Resort Country Club—a course with its own connection to the Dye family. Pete Dye and his brother Roy had actually begun work on the site in the late 1960s, only for the original developer to go bankrupt before paying them; the course was finished without their input and opened in 1971. Rather than simply updating that layout, ownership chose a more ambitious path: invite Pete Dye back to reimagine the course he had worked on decades earlier.

Only club members, their guests, and Inn guests can play the Links at Perry Cabin. [credit: Inn at Perry Cabin]

Working late in his career alongside Alice Dye and P.B. Dye, the architect approached the project as a genuine second opportunity. The Dyes undertook a ground-up reimagining to create a course that finally lived up to its waterfront setting.

Along the way, fairways were rerouted, greens rebuilt, strategy sharpened, and new practice facilities added, transforming a pleasant but ordinary resort layout into a tighter, more strategic course marked by clearer Dye hallmarks throughout.

Reopened in 2018 as the Links at Perry Cabin, the course stakes its claim as the final design personally shaped by Pete Dye, who passed away in 2020. Its addition didn’t change the inn’s maritime identity so much as broaden it—a place where mornings might begin on the course, afternoons on the courts or water, and evenings drift back to the waterfront lawn.

Links at Perry Cabin: The Golf Course

The Links at Perry Cabin blends signature challenges with the Chesapeake landscape. [credit: Inn at Perry Cabin]

Just two miles from the inn, the Links at Perry Cabin is a private club that can be played by members, their guests, and overnight guests of the Inn at Perry Cabin. If the course stands as Pete Dye's final work, it's fitting that signature Dye cues define the routing: railroad ties lining pot bunkers and hazards, angled fairways demanding precision, and large, undulating greens. From the back markers it plays a full 7,023 yards against a par of 72 and a slope of 148—numbers that leave no doubt about the teeth behind the postcard scenery—though five sets of tees bring it down to a far friendlier 4,881 yards for players who'd rather enjoy the views than fight for them.

The front nine threads tree-lined corridors, and the opening suggests this is not going to be a diabolical test. Each of the first three holes is on the shorter side and doglegs to the left, giving players of every ability a chance to get off to a good start before Dye starts asking harder questions.

The routing weaves through mature trees, creating a secluded feel across the course. [credit: Inn at Perry Cabin]

The most memorable hole on the front nine is the 7th, a par three built on the Biarritz template—a design about as old as American golf architecture itself. The design (first called “the Chasm”) takes its name from the Biarritz Golf Club in France, where Willie Dunn Jr. built the original in 1888. The Biarritz became a favorite of Golden Age architects C.B. Macdonald and Seth Raynor, who spread its long, narrow, swale-bisected green across some of the country's most storied courses. Dye rarely borrowed template holes the way his predecessors did, which makes the 7th at the Links at Perry Cabin an outlier in his catalog.

At roughly 245 yards from the tips with a pond guarding the right side, the hole demands a long, accurate strike—but the real test waits on the green itself, where a deep swale splits the putting surface into front and back tiers. Land on the wrong shelf and the swale can send a two-putt spiraling into three or four; find the correct level and the hole yields one of the round's better birdie chances. It's a rare piece of golf history planted in the middle of a Dye design, and it's worth savoring for that alone.

The Biarritz-style 7th hole introduces a piece of classic golf course architecture to the Links. [credit: Inn at Perry Cabin]

The back nine trades that history-lesson variety for a more familiar Dye vocabulary: lakes, sand, and smaller margins for error. Trees and houses block views of the water for most of the stretch, with the exception of a few glimpses from the 18th tee and green—though the breeze off the water is felt well before you can see it. The biggest threats to par are the lakes running laterally alongside the fairways on the 10th, 12th, and 15th, while the par-5 14th is defined by a set of expansive waste bunkers. Throughout, the challenge mounts steadily: fairways tighten, and the greens are more severely guarded than anything the front nine offers.

The real flourish—and the course’s most archetypal stretch—is the closing "Goodnight Kiss"—holes 16, 17, and 18. It starts with a drivable par-4 that tempts players to be bold off the tee. The 17th channels the 17th at TPC Sawgrass, its island green introducing the same pulse-quickening tension as its famous inspiration. Sealing the “Kiss” is a par-4 that bends sharply around a lake to an enormous tiered green, where views of the harbor and Chesapeake Bay shine beyond—the kind of finish that closes the round with a memorable photo.

The Links strives to give golfers a seamless experience from start to finish. With access limited to members and Inn guests, the course is generally uncrowded, facilitating a brisk pace of play. It's a comfortable walk, though the routing doesn't return to the clubhouse until the round concludes. The pro shop's eight HD golf simulators, loaded with many of the game's greatest courses—Pebble Beach and the Old Course among them—mean a rainy day doesn't have to be a lost one. Inn guests may easily pair mornings on the course with afternoons on the water, on the courts, or in town—Dye's final signature woven into a Chesapeake weekend.

Inn at Perry Cabin

The Inn at Perry Cabin reveals itself gradually. Guests arrive through a quiet rear court off St. Michaels Road, following a red brick entry lane that culminates beneath a modest porte cochère that offers little hint of the waterfront setting beyond. Only after stepping inside—and moving through a sequence of intimate rooms—does the Miles River suddenly appear, spreading wide beyond the lawn. The effect feels intentional: less a grand hotel arrival than the discovery of a private Chesapeake estate opening naturally toward the water.

The original 1816 manor anchors the heart of the property, its low corridors and fireside sitting rooms connecting older guest wings with later expansions added during the Ashley and Belmond eras. The inn’s 78 rooms and suites are spread across three levels, maintaining a residential scale that never overwhelms the landscape. Interiors blend coastal whites, nautical brass accents, and traditional furnishings, with many rooms and suites offering fireplaces, verandas, or terraces oriented toward gardens or river views.

Guest rooms pair classic furnishings with coastal touches and a residential sense of comfort. [credit: Inn at Perry Cabin]

Movement through Perry Cabin favors discovery over efficiency. Brick paths wind past secluded courtyards, flowering gardens, and croquet lawns before opening onto the signature great lawn—a broad sweep of grass facing the Miles River where sailboats can be seen and guests may gather. Adirondack chairs line the waterfront, and the day naturally pulls outward toward the view.

Public spaces follow the same outward orientation. Stars, the inn's signature restaurant, holds the prime riverfront corner, with Purser's Pub sitting just inland as a warm fireside counterpoint for evening cocktails. The spa and pool are discreetly tucked among mature trees, while the Har-Tru tennis courts blend into the estate grounds.

The progression—arrival court to manor rooms to open waterfront—mirrors the pace of a stay itself: unhurried, layered, and always drawing guests back toward the water.

Dining and Cocktails

Stars’ outdoor terrace extends dining toward the Miles River and passing sailboats. [credit: Inn at Perry Cabin]

Dining at the Inn at Perry Cabin follows the same outward pull as the rest of the property—toward the water and the easy rhythms of the Chesapeake.

Stars, the inn’s signature restaurant, occupies the prime riverfront setting, its terrace extending toward the Miles River and the quiet movement of passing sailboats. The menu changes frequently, shaped by Chesapeake seafood, nearby farms, and ingredients drawn from the inn’s gardens. The approach feels refined without becoming formal, with dishes such as local rockfish, Eastern Shore oysters, and seasonal preparations that suit the relaxed waterfront setting.

Purser’s Pub provides a more casual small-plates option. Its club-like warmth makes it a natural gathering place after a round of golf or an afternoon sail, especially on cooler evenings when the fireplace becomes the center of the room. In warmer months, guests often spill onto the terrace around the courtyard’s focal-point fire pit. Guests can sample rare whiskeys and cocktails freshened with cuttings from the inn’s herb garden, along with seasonal offerings from St. Michaels Brewery and Lyon Distilling Company. It all unfolds under soft lighting as evening settles over the harbor.

Stars showcases Chesapeake flavors with seasonal dishes and locally sourced ingredients. [credit: Inn at Perry Cabin]

For something even more casual, the High Tide Pool Bar keeps food and drinks flowing poolside—a good option for a lunch or a timely light bite that doesn't require changing out of a swimsuit.

A seasonal highlight is the inn’s private waterside dining experience. From spring through fall, small dining houses along the shoreline host multi-course tasting dinners with dedicated service, turning an evening meal into something more memorable—part celebration, part immersion in the setting itself.

While the inn easily supports a full culinary weekend on property, St. Michaels expands the range just a short walk or bike ride away. Limoncello Restaurant & Wine Bar brings lively Italian energy, and Bistro St. Michaels offers a more intimate European-influenced approach to Chesapeake ingredients. For a polished night out, Theo's Steaks, Sides & Spirits pairs hand-carved steaks with a New Orleans-inflected, art-filled dining room, while next door, Ava's Pizzeria & Wine Bar keeps things looser with wood-fired pizza and a lively bar scene — all reinforcing one of Perry Cabin's practical advantages: a weekend where the car can remain parked while the experience expands naturally outward from the inn.

Perry Cabin's own gardens supply herbs for cocktails and seasonal dishes. [credit: Inn at Perry Cabin]

Sailing, Racquets, and Shore Pleasures

From Hinckley yachts to sunset sails, the water is never far during an Inn at Perry Cabin getaway. [credit: Inn at Perry Cabin]

While golf may be the newest addition to Perry Cabin’s story, life at the inn still revolves around the water. The private marina sits just beyond the great lawn, where a dedicated boating concierge coordinates daily excursions aboard a fleet that includes Hinckley yachts, Harbor Star, a French canal boat designed for slower explorations of the shoreline, classic sailboats, and the historic 1902 Stanley Norman, the last of the skipjacks that plied the Chesapeake Bay dredging for oysters.

Special weekends revolve around the rhythms of the sailing calendar, beginning with the Inn’s annual Return of the Fleet, when the boats come home to the Miles River and a new season gets underway.

During the sailing season, guests can join group sails, arrange private charters, or settle into sunset cruises where cocktails arrive as the Miles River turns gold in the evening light. For many visitors, time on the water becomes less an activity than a rhythm of the stay—a natural extension of mornings on the course or afternoons lingering along the lawn. Advance reservations are wise during peak season, when calm weather quickly fills the sailing schedule. Of course, guests who want to learn how to sail can do that too, with private sailing lessons offered on the Miles River.

Bocce offers an easygoing lawn-side diversion for guests of all ages. [credit: Inn at Perry Cabin]

On land, three Har-Tru tennis courts sit street-side near the fitness center, bordered by a white lattice fence and partially shaded by trees. Seasonal clinics and lessons lend the area an easy social energy. Closer to the lawn, croquet and bocce courts offer a more relaxed alternative that is popular with kids and adults alike.

The Spa at Perry Cabin rounds out the estate's more restorative side. Its seven treatment rooms draw on botanicals grown in the Inn's own gardens and from neighboring Eastern Shore farms—the same herbs that turn up in cocktails at Purser's Pub find their way onto the treatment menu as well. Just outside, a zero-edge outdoor pool is flanked by the High Tide Pool Bar, keeping food and drinks within easy reach of a lounge chair.

Beyond organized activities, Perry Cabin offers plenty of ways to explore the property on your own. Complimentary bicycles make the short ride into town effortless, while garden paths, gazebos, and quiet corners across the property invite long stretches of reading or conversation. Seasonal programming deepens the connection to place: painting classes led by a local artist unfold outdoors with supplied materials, and guided walks with the inn’s horticulturalist explore the estate’s gardens, orchards, and native wildflowers—experiences that feel less scheduled than naturally shared.

For golfers who'd rather be on the water than off it between rounds, our guide to The Coeur d'Alene Resort explores a very different setting built around the same idea—a floating green, a lakeside hotel, and no shortage of ways to get out on Lake Coeur d'Alene.

Touring St. Michaels

Talbot Street anchors St. Michaels with shops, galleries, restaurants, and local character. [credit: Inn at Perry Cabin]

Just beyond the inn’s grounds, St. Michaels provides the rare luxury of a destination best explored without a car. A short walk or bike ride leads into one of the Eastern Shore’s most appealing small towns, where a few compact blocks hold antique shops, galleries, and locally owned boutiques clustered along Talbot Street and nearby streets.

Dining, tasting rooms, and casual gathering places appear naturally along the way, from restaurants and cafés to a brewery, distillery, and winery that reflect the town’s easygoing social character. The inn also offers guided history tours—on foot or by bicycle—that place the harbor and surrounding streets in context, revealing how a working maritime town gradually evolved into a weekend retreat while preserving much of its original character.

A highlight for many visitors is the Chesapeake Bay Maritime Museum, located just down the waterfront from the inn. Spread across an 18-acre campus, the museum brings the region’s boatbuilding and seafaring traditions to life through restored vessels, hands-on exhibits, and the Hooper Strait Lighthouse, which offers sweeping views across St. Michaels Harbor.

The Chesapeake Bay Maritime Museum preserves the region’s rich boatbuilding and maritime heritage. [credit: Inn at Perry Cabin]

Despite its popularity, the town retains a remarkably relaxed character. There are no traffic lights, and days tend to unfold at a walking speed that feels increasingly rare along the East Coast. It’s easy to understand why weekends draw visitors from Washington, Baltimore, and Philadelphia—and just as easy to understand why many arrive planning a short stay and begin thinking about their return before the weekend ends.

If a small, atmospheric town within walking distance of your hotel is part of what makes a golf weekend memorable, our guide to The Otesaga & Leatherstocking Golf Course in Cooperstown offers a similar rhythm—lake, historic inn, and a walkable village anchored by the Baseball Hall of Fame.

Getting There and When to Go

Waterfront firepits create an inviting setting for lingering after sunset. [credit: Inn at Perry Cabin]

Set along Maryland’s Eastern Shore, the Inn at Perry Cabin sits roughly 90 minutes from both Washington, D.C., and Baltimore, and about two and a half hours from Philadelphia—close enough for an easy long weekend, yet far enough to feel genuinely removed from urban pace.

For those flying, the most convenient major gateways are Baltimore/Washington International Thurgood Marshall Airport (BWI) and Ronald Reagan Washington National Airport (DCA). Nearby Easton Airport (ESN), located about 25 minutes from the resort, primarily serves private aviation and offers the most convenient arrival for guests traveling by charter or personal aircraft.

Most guests arrive by car, though the journey itself can become part of the experience. In addition to the Skip the Bridge weekend package, private boat transfers across the Chesapeake Bay from Annapolis can be arranged through the inn—a memorable arrival that immediately sets the tone. Once checked in, there’s little need for car keys; nearly everything guests might want lies within walking or biking distance. The inn’s on-call shuttle provides another easy option for reaching town or the golf course.

The Inn remains open year-round, but spring through fall is when St. Michaels truly shines. Sailing, tennis, and outdoor dining tend to define the warmer months, and the golf course is at its most scenic from April through October, when emerald fairways meet Chesapeake breezes. Autumn brings crisp air and quieter midweek escapes, while winter reveals a different personality altogether—fireplaces lit, crowds gone, lower rates, and a distinctly cozy charm that suits the inn’s historic character. Regardless of season, visitors quickly notice one defining trait of the town: evenings wind down early, reinforcing the unhurried pace that defines a stay here.

Is the Inn at Perry Cabin Right for You?

Railroad ties and an island green are just two of Pete Dye's favorite design elements on the Links. [credit: Inn at Perry Cabin]

The Inn at Perry Cabin ultimately succeeds not because of any single feature—not the golf, the sailing, or even the storied history—but because all of them move in quiet harmony with the rhythms of the Chesapeake. For the right traveler, it delivers a rare balance of elegance, intimacy, and genuine sense of place.

Ideal for:

Pete Dye enthusiasts eager to experience one of the legendary architect’s final personal designs in a relaxed, uncrowded setting
Couples seeking romantic escapes shaped by sunset sails, waterfront cocktails, and unhurried evenings
Solo travelers who appreciate an atmosphere refined enough to feel special yet relaxed enough to feel comfortable on their own
Eastern Shore explorers using St. Michaels as a base for nearby towns such as Oxford, Tilghman Island, and Cambridge
Water lovers drawn to daily boating opportunities and easy access to the neighboring Chesapeake Bay Maritime Museum

May not be the best fit for:

Budget-focused travelers, as rates reflect an independent luxury resort experience
Golfers seeking multiple courses or dramatic mountain-style visuals rather than a single strategic design
Nightlife seekers, given that St. Michaels typically quiets down after about 10 p.m.
Families wanting high-energy programming, as the tone leans romantic and restorative rather than activity-packed
Travelers uninterested in maritime culture, since much of the destination’s charm flows from its connection to water and history

This feature draws on a firsthand visit hosted by the Inn at Perry Cabin and has been refreshed with current research to reflect the property as it stands today.

You May Also Enjoy …

If you enjoyed this look at the Inn at Perry Cabin & Links at Perry Cabin, you might also like these Weekend Golf Getaways destination guides:

• Enchantment & Seven Canyons Golf Club (Arizona) — Red-rock scenery, the nationally renowned Mii amo spa, and one of the Southwest's most memorable golf settings.

• The Omni Grove Park Inn (North Carolina) — Historic Asheville resort with a restored Donald Ross course and one of America’s great destination spas.

• Forest Dunes (Michigan) — Pure golf immersion featuring Tom Weiskopf’s original championship course, Tom Doak’s reversible Loop, and the Bootlegger short course.

• The Otesaga & Leatherstocking Golf Course (New York) — A century-old lakeside hotel beside a Devereux Emmet classic, with Cooperstown and the Baseball Hall of Fame just a walk away.

Planning your next golf getaway?

Browse all Weekend Golf Getaways destination guides for in-depth coverage of golf resorts, memorable courses, accommodations, dining, and experiences worth building a trip around.