27 Best Hotels in The Eastern Shore, Maryland

This compound of castles is a popular family destination for its sheer amount of kid-friendly amenities. "Castle Kid" activities include tales of pirates and ghosts of Assateague Island told by Captain J. one night a week in summer, and Lady Sunshine is on hand to pamper young princesses. All rooms are basic, with pastel walls and random, motel-esque furniture. But all are oceanfront, looking onto a wide swath of beach, with some overlooking the largest pool in Ocean City. Two off-site cottages a block away provide a cozy home-away-from-home atmosphere.

Family-owned and -operated since 1923, the three-story, H-shaped frame hotel—Ocean City's oldest—is a replacement of the original Victorian hotel, opened on July 4, 1875, that was destroyed as part of the Great Ocean City fire of 1925. The present structure was quickly rebuilt by 1926, its rooms today plainly furnished and decorated just as they were originally, but now with modern comforts, such as private baths and air-conditioning throughout. A rooftop deck affords truly panoramic views over the ocean and the Bay.

This fully restored 1895 inn blends the taste of grand living with modern conveniences. Spacious, hardwood-floor guest rooms all offer four-poster beds. The second-floor parlor, done in bold red-and-green hues with ornate furnishings, is a perfect place to escape with a fat book or a stack of magazines. The curved entry drive has been closed to vehicles and landscaped into a delightful people-watching alfresco lobby. Beneath sparkling chandeliers, the The Drummer's Café ($$$) serves scrumptious entrées that may include crab cakes, rack of New Zealand lamb, and Grandma's Twin Chicken.

Natives Jordan and Alice Lloyd returned to their hometown and bought a 220-year-old home (the former Inn at Easton) right in the center of town. They restored the inn, creating seven guest rooms and suites, each named after a different variety of pear. Impeccable hosts, the Lloyds considered every detail, from the luxurious sheets to the brightly colored walls.

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 miles south of downtown Chestertown, this mid-19th-century inn, known for its gracious hospitality, still resembles the plantation house it once was. The brick building's entrance has a 3½-story walnut-and-ash staircase, pine floors, and plaster ceiling medallions. All of the spacious, well-appointed guest rooms have working fireplaces (but only lit October through April), and five have hot tubs. Classic movies, available from the innkeepers' private collection, can be viewed in the library, which also has an extensive supply of books. Rates include a full country breakfast and afternoon tea with homemade pastries.

This 1730 brick manor house, together with the carriage house and the Oxford cottage, is set amid magnolias and willows on the banks of Island Creek, a few minutes' drive from Oxford. Inside are five arched fireplaces, floral chintz fabrics, and polished wood floors. All the rooms and suites of this luxurious B&B have water views and are furnished with English manor–style antiques, including four-poster and canopy beds. Some also have hot tubs and working fireplaces; the two-bedroom carriage house has a kitchen.

A 20-minute drive from North East, Elk Forge is nestled among 5 acres of woods and gardens along Big Elk Creek. Each of the 12 guest units is beautifully furnished and uniquely decorated, inspired by area locales and cultures, and creature comforts are plentiful. A daily afternoon tea includes the innkeepers' own herbal blends; services at the Spa in the Garden include Swedish massage and aromatherapy facials. With easy access to sites of interest in Delaware and Pennsylvania as well as Maryland, Elk Forge is indeed a mini-resort.

Three circa-1860 houses have been turned into an elegant and comfortable getaway. All rooms have a private porch or balcony, and all are decorated with antique furnishings, fine linens and towels, and down comforters. The hot stone massage and invigorating rosemary mint body wrap are treatments in the spa. Refreshments are served daily at 3. The bed-and-breakfast home also emcompasses a fine needlepoint shop, B's Stitches, and an upscale pet boutique, Flying Fred's.

On 12 acres sloping gently to a gazebo on the edge of its private Chesapeake beach, this stately 18th-century Georgian brick manor house provides a taste of Eastern Shore gentility. Its antique furnishings and Oriental rugs, along with an airy sun porch, re-create a bygone era. Of its 11 impeccably decorated guest rooms, five have working fireplaces. The manor's formal library is well stocked with both books and films. If needed, guests are provided transportation to the restaurant of their choice for dinner. Golf and tennis are available at neighboring Great Oak Landing.

This 370-acre complex is the Eastern Shore's first full-service, year-round resort, and one that takes full advantage of the soothing natural light and spectacular views of the Choptank River. The resort encompasses an 18-acre Blue Heron rookery, an 18,000-square-foot spa, and a golf course designed by Keith Foster. All rooms and suites have a private balcony; those on the upper level have raised ceilings. The resort's restaurants include the self-service Bay Country Market and the Blue Point Provision Company for seafood. Two outdoor sandstone fireplaces make perfect s'more hubs, and a 30-foot-high wall of windows welcomes you to Michener's Library.

This three-story brick structure on Chestertown's main street was built in 1903 for traveling salesmen. Today it is a gathering center for residents and visitors alike. Guest rooms and suites with authentic period furnishings, as well as custom-designed and handcrafted pieces, some of which hide TVs and telephones, strive for a blend of 20th-century eras. The hotel's four dining areas ($$$), including one outside in the summertime, all serve traditional Eastern Shore fare like crab cakes as well as locally sourced poultry, meat, and vegetables.

On 30 lush acres along Swan Creek, this stately Colonial-era building welcomes guests with brick fireplaces and exposed beams; four-poster, canopied beds; and a spacious two-room Escapade suite with French doors and a marble bath with a whirlpool hot tub. Yet it's worth staying here for the views alone. At the inn's restaurant ($28) regional fare is served—the cream-of-crab soup with sherry is a favorite among regulars, as are entrées such as Maryland jumbo lump crab cakes and pan-seared duck breast. It serves dinner Wednesday through Saturday and brunch on Sunday. Osprey Point Marina, with 160 slips, welcomes transient boaters year-round.

On 25 acres beside the Miles River, this luxury inn—operated by the world-renowned Orient Express Hotels group—employs a nautical theme throughout to elegant effect. Each unique guest room has elegant appointments; amenities include heated towel racks, fresh flowers in all rooms, and afternoon tea. Above all, staying here means impeccable service. Dining at the inn's restaurant with its exquisite cuisine and stellar wine selection is an event. The signature crab spring roll with pink grapefruit, avocado, and toasted almonds, and the lamb shank glazed with honey and tarragon are both exquisite.

Located in a town that's separated by water from the other two villages on Smith Island, this remote English cottage–style inn takes its soothing name from a phrase in a poem by the mystic St. John of the Cross, a Carmelite monk. The rooms are small with antique linens and big windows. Tylerton has no restaurants, but, for an extra charge, the eclectic innkeepers will cook a fresh seafood dinner for guests.

A summer hotel since 1898, this imposing antebellum manor house is on 226 acres of farmland along Thompson Creek near the Chesapeake Bay. Many guest rooms have cozy window seats, others boast Italian marble fireplaces. All rooms on the upper floors open onto semiprivate verandas. The in-house restaurant serves breakfast daily and lunch and dinner, Wednesday through Sunday in two elegant Victorian dining rooms or in an enclosed porch.

Opened in 1924, the Lankford is still owned by the family of the original owners. Many combinations of rooms in the hotel and the adjacent lodge are available for small groups of friends and families. Bicycle storage and Ocean City Golf Course privileges are included in the rate. Lazing in a rickety rocking chair on the front porch off the small (un-air-conditioned) lobby, cooled by overhead fans, is a true throwback to quieter times. (All guest rooms are air-conditioned.)

This elegant boutique hotel is a Chesapeake Bay lighthouse lookalike of quiet luxury, just blocks from the busy Coastal Highway. Its airy, contemporary suites have high ceilings and views of sand dunes that slope to Assawoman Bay. Suites have white-cushion rattan furniture and marble bathrooms, some with two-person hot tubs, and the allure of wet bars and fireplaces. Sliding glass doors lead to private decks with steamer chairs.

Located on a rise overlooking the river, this elegant turn-of-the-20th-century country home was the first bed-and-breakfast in the county (1986) and remains one of the most charming. Accommodations include the delightfully contemporary second-floor room called Sarah's Loft, named for the original innkeeper. Don't sleep through breakfast or you might miss cranberry French Toast made with sourdough bread, Chesapeake puff pancakes, or phyllo dough egg blossoms, freshly made and hot from the oven and often served out on the screened-in porch. Guests feel like personal guests of the innkeepers and their two young sons.

Antebellum grace defines this 1748 mansion on 17 acres along the banks of Oak Creek, 3 miles from St. Michaels. The antique-filled inn has a stunning black-and-white tile foyer; its best rooms have fireplaces, private porches, and hot tubs. The day starts with a full country breakfast served in the sunny yellow-and-red dining room. After that, you might want to go fishing off the pier, or head no farther than one of the rockers in the screened porch overlooking the water.

Filling a need for more affordable, family- and child-friendly accommodations, this small, multistory hotel on the boardwalk is owned and operated by a family with over a century of experience. All rooms are efficiencies with fully equipped kitchenettes and sofa beds. Some have extra-long beds and hot tubs. Conner's Beach Café, a full-service restaurant, and Conner's Sail Loft Deck Bar, a beachside bar and restaurant, are part of the complex.

With its welcoming front porch, this Victorian home and its adjacent cottages are on two lovely acres on the banks of the Pocomoke River. This small inn, on the National Register, is impeccably appointed and maintained, including the lovely gardens. Decor is traditional Early American.

In the early 1700s this building on the banks of the Tred Avon River was crafted as a home by ships' carpenters using ship nails, hand-hewn beams, and pegged paneling. In 1738 it was bought by an English trading company as a house for its Oxford representative, Robert Morris. Four guest rooms have handmade wall paneling and fireplaces built of English bricks used as boat ballast. Other buildings in the complex include a newer manor house on a private beach. Breakfast is included. Several years ago the inn closed its famous restaurant (with its reputed "best crabcakes on the bay"), but in 2010 it reopened, redecorated, and rehabilitated, under celebrity chef Mark Seller, who promotes locally sourced food. The kitchen has regained its former glory.

Three levels of broad decks mean that every room has a place from which to relax and watch all manner of watercraft, including international shipping vessels, sail in and out of the Chesapeake & Delaware Canal just yards away. (A canal-side hot tub offers an even closer view.) Built as a residence in 1920, this elegant, waterfront B&B blends eclectic furnishings with modern amenities. The decades-old black-and-white photos hanging in the public areas reveal much about the roles the owner-innkeepers' families played in the history of Chesapeake City. The Ship Watch is one of several B&Bs in Chesapeake City.

Beyond the entry archways of this stately, four-story brick hotel, an early-20th-century aura pervades its spacious common areas, which are enhanced by huge fireplaces and paintings of old Easton. Mahogany reproduction furniture fills the guest rooms, most in greens and golds. In the hotel's full-service dining room a "hunting breakfast" is available early every morning in season. To one side of the porte cochere, broad awnings shade an alfresco lobby and sometime dining area. A small on-site spa offers manicures and massages. Built in 1949, the Tidewater is a member of the Historic Hotels of America.

Warm and welcoming conviviality and casual elegance define this compact, modern resort overlooking the Chesapeake Bay and a waterfowl marsh. Decor and furnishings throughout are bright and modern, with lots of white enhanced by splashes of color. Five deluxe waterside suites have hot tubs, fireplaces, and spacious decks. The 5-acre complex includes a 20-slip transient marina and a small fleet of tandem and single kayaks available for rent. Dishes served at the Gallery Restaurant ($$–$$$) are at once innovative and traditional, enhanced by a well-selected wine list.

Adirondack chairs line a sloping expanse of lawn leading to the formal gardens of what was once a Civil War army officer's home. Set on the town's harbor and across a footbridge from the Maritime Museum, this inn is a relaxing haven. All rooms include queen-size beds; two have fireplaces, and three overlook the water. The suite has a private water-view deck and a fireplace as well as a TV. There's a nightly happy hour that includes wine, beer, and light hors d'oeuvres. No children under 13 are allowed on weekends.

Step back in time at this inn restored to its appearance circa 1790. Built as a home in 1733, it was a tavern, then a general store; it may be the town's oldest building. Brick fireplaces and deep window seats, an old writing desk, and pewter candleholders are all in keeping with its Colonial past. The original kitchen, shaded by a giant elm, is the inn's most requested guest room—its rough ceiling beams, brick floor, and large fireplace attest to its antiquity. Afternoon tea is served in the dining room, on the rear stone patio, or in guest rooms.