1 . Brampton Bed and Breakfast Inn

Chestertown, Maryland

CALL DIRECT: +1 (410) 778 - 1860

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Housed inside a plantation house, circa 1860, and located just one mile outside of Chestertown, MD, our No. 1 pick has all the history, elegance and authentic touches that traditional bed and breakfast fans crave. For this reason alone, Brampton Bed and Breakfast Inn won our hearts – and our No. 1 spot.

Brampton Bed and Breakfast Inn lets you choose from guestroom or cottage accommodations, each with unique 19th-century charms. Beds draped with delicate floral linens and handcrafted lace canopies, oriental rugs placed at your feet and antiques scattered around the cozy hearth of your wood-burning fireplace – if Brampton’s interiors aren’t the essence of bed and breakfast, we don’t know what is! Of course, all this turn-of-the-century charm has been accented with the modern amenities that today’s travelers crave, including air conditioning, flat screen TVs and en-suite baths with whirlpool tubs. Mulberry Cottage, our personal favorite, is sure to inspire sweet romance, be it the rekindling of old flames or the striking of sparks for relatively young loves. Its front porch comes with your choice of seating; snuggle up on the wooden swing for two or hole up in a hammock as you admire the surrounding meadow from your lofty perch. A backyard patio, enclosed for added privacy, hides an outdoor shower and spacious soaking tub amidst its fragrant gardens.

Address

25227 Chestertown Rd., Chestertown, MD 21620

Highlights

Every Brampton Bed and Breakfast stay includes an afternoon tea service in addition to the innkeeper’s tasty breakfast. Fresh baked goods, tea and coffee are served for your refreshment pleasure.

Fun facts

Brampton Bed and Breakfast offers Elopement Packages for those looking to forgo the fuss of wedding planning and say “I do” on the inn’s scenic and historic grounds.

2 . Great Oak Manor

Chestertown, Maryland

CALL DIRECT: +1 (800) 504 - 3098

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Our No. 2 spot occupies a grand Georgian mansion overlooking Chesapeake Bay. With its early 20th-century grace and elegance, this charming waterfront bed and breakfast is as close to time travel as you’re apt to get. Relive the Eastern Shore’s golden days at Great Oak Manor.

Our No. 2 pick’s story begins in 1938, when it was handcrafted with bricks salvaged from the ballast of the W.R. Grace. A spiral staircase and furnishings comprised of mainly antiques and period pieces lend even more historic charm to Great Oak Manor. Its guestrooms, which occupy a fine stretch of real estate on the Chesapeake waterfront, house plush featherbeds, while a music room, conservatory and well-stocked library – rare finds in modern times – round out this Eastern Shore inn’s offerings. Grand Oak Manor has even resurrected the five course dinner, a true culinary delight in the microwave age. Historic Chestertown, the Maryland city that Great Oak Manor calls home, boasts its own rich history dating back to the early 1600s. Its choice location on Chesapeake Bay made Chestertown’s port of considerable use to early colonial settlers. Today, its past is lovingly preserved in cobblestone streets lined with 18th-century homes and churches. And its antique shops, art galleries and a generous selection of restaurants make it a wonderful place to pass an afternoon or entire day during your Maryland vacation.

Address

10568 Cliff Rd., Chestertown, MD 21620

Highlights

Great Oak Manor’s hot breakfast buffet includes seasonal fresh fruit, homemade muffins, cold cereal and a hot entrée of French toast, quiche or egg strata.

Related activities

Great Oak Manor partners with Gooseworks Consulting to provide intriguing team building activities for your Maryland meeting or special occasion.

3 . The Parsonage Inn

St. Michaels, Maryland

CALL DIRECT: +1 (410) 745 - 8383

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With its brick exterior, intricate porch latticework and storybook steeple, our No. 3 pick is straight out of a Victorian painting. One day spent exploring the charming seaside town it hails from, however, and you’ll be thankful The Parsonage Inn is actually a Maryland accommodation, rather than a work of art.

Built by the founder of the St. Michaels Brick Company as a showpiece for his trade, the two-story Victorian this Maryland inn calls home is equally impressive in the modern day. Its historic bricks take on a pinkish hue come sunset; pull up a wicker chair on the inn’s front porch for spectacular views of St. Michaels in all its splendor. Rooms with brass beds, wood-burning fireplaces and private baths pair historic charms with modern comforts. And with the inn’s own fleet of Raleigh bikes at your disposal, attractions like Harbortowne’s golf course are only a short pedal away. Culinary enthusiasts will meet their match in The Parsonage Inn’s “Taste of St. Michaels” packages, which feature local favorites like 208 Talbot and the Key Lime Café. This quaint Maryland town also houses a craft brewery and winery within its borders, for those whose interests lie more with libations. And the inn’s own gourmet breakfast is nothing to scoff at, especially with tasty dishes like lemon ricotta soufflé gracing your plate.

Address

210 N. Talbot St., St. Michaels, MD 21663

Highlights

The Parsonage Inn is within walking distance of the harbor, and local favorites like the Chesapeake Bay Maritime Museum are just across the street.

Related activities

Fishing, golf, kayaking, horseback riding, sightseeing and sailing.

4 . Lake Pointe Inn

McHenry, Maryland

CALL DIRECT: 1-800-523-LAKE

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Our next Maryland bed and breakfast takes us away from the Eastern Shore and into the heart of mountain country. More lodge than typical Maryland inn, Lake Point Inn was inspired by the early Arts and Crafts traditions of the region, and is rife with architecture and furnishings pulled from the era.

Deep Creek Lake is a sight to behold in every season and the luxury inn poised on its banks makes for a truly serene Maryland escape in all four. Wake to a scrumptious breakfast each morning, pass the afternoon on neighboring slopes or hike McHenry’s mountainous terrain, and return just in time for Lake Pointe Inn’s afternoon hors d’oeuvres. A leisurely cruise aboard the inn’s pontoon boat, The Tight Squeeze, follows this tasty treat in warmer months, while optional massage treatments – including hot stone therapy and reflexology – are a welcome alternative come winter. This Maryland lodge even offers discounted lift passes for Wisp Ski Resort, conveniently located just across the road! The Buffalo Marsh Suite, with its half walls topped with warm wood columns, is a stunning example of the architectural styles of Frank Lloyd Wright. And its amenities – a separate seating area with gas fireplace, private bath with spa tub and steam shower, and windows that frame views of Marsh Hill Mountain – are the epitome of luxury accommodations.

Address

Lake Point Inn guestrooms and suites are appointed with plush towels and robes, fine Italian linens, flat screen TVs, Bose CD players with MP3 compatibility and upscale bath amenities.

Related activities

Tennis, Bocce ball, croquet, skiing, snow tubing and snowshoeing.

5 . Cambridge House

Cambridge, Maryland

CALL DIRECT: +1 (410) 221 - 7700

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This delightful manor in Cambridge’s historic district was once the former residence of a Cambridge sea captain, and today serves as a Maryland inn. From its charming red and white exterior to cozy rooms that blend that best of old and new, Cambridge House provides every comfort on your Maryland vacation.

Cambridge’s historic High Street beckons from beyond the parlor window, but we bet you’ll hardly notice – you’ll be too occupied with your Cambridge House suite’s exquisite interior to spare a moment’s glance at your surroundings, scenic as they may be. This Maryland inn boasts six spacious guestrooms in all, each appointed with its own unique blend of plush carpets or hardwood floors, delicate striped or floral wallpapers, and oil paintings or mirrors tucked into gilded frames. Wood-burning fireplaces framed with wingback chairs, private baths appointed with claw foot tubs – no detail was spared in the makings of this Maryland inn! Tasty picnics in Long Wharf Park. Scenic cruises aboard the Choptank Riverboat Company’s reproduction paddle wheelers. And murder mystery parties that feature a full tea service complete with scones, finger sandwiches and plenty of sleuthing. With packages for all of the above and much more, Cambridge House caters to every interest!

Address

112 High St., Cambridge, MD 21613

Fun facts

Cambridge House is a proud member of the Green Hotels Association and employs eco-friendly practices such as toxic-free cleaning and buying local or organic products.

Related Onsite Offerings

The Cambridge House is available for Maryland business meetings, reunions and special events.

6 . The Annapolis Inn

Annapolis, Maryland

CALL DIRECT: +1 (410) 295 - 5200

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With its pale yellow exterior, white crown molding and elegant shuttered windows, it’s hard to imagine our No. 6 pick was constructed more than two centuries ago. Fittingly housed in the heart of Annapolis’ historic district, this Maryland townhouse-turned-inn has even had the honor of welcoming six signers of the Declaration of Independence.

This Maryland inn’s ornate spaces serve as remarkable examples of Greek revival style. Salons take the place of traditional living rooms, and are adorned to reflect the Annapolis Inn’s historic significance with exquisite crystal chandeliers, marble fireplaces and rosette moldings. Richly-colored tapestries and paintings adorn the parlor walls, with authentic Oriental rugs protecting the dark walnut and pine plank floors – a rare find in modern Annapolis homes. The inn’s crowning achievement, the Dr. James Murray Suite, opens to reveal a sitting room enclosed with panes of etched glass and an ornately-appointed private bath of imported Italian marble and porcelain sinks. The Annapolis Inn’s exquisite interiors open to reveal an equally stunning backyard composed of beautifully-maintained gardens, old growth shade trees and fan-tailed fish that flit below the lily pad-strewn surface of a Koi pond. The inn’s third floor sundeck offers sightseeing opportunities of its own, with sights like the State Capital and the Naval Academy Chapel’s dome clearly visible from its lofty heights.

Address

144 Prince George St., Annapolis, MD 21401

Highlights

Scattered rose petals, a bottle of champagne, chocolate-covered strawberries and gift baskets can all be added to your Annapolis Inn suite at your request.

Related activities

Walking tours, sailboat charters, sunset cruises, sailing lessons, fishing and golf.

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