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.
25227 Chestertown Rd., Chestertown, MD 21620
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.
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.
Friendly innkeepers are easily one of our No. 2 pick’s finest features, with its Annapolis address coming in a close second. Royal Folly invites you to make the most of your host’s gracious hospitality – and this vibrant Maryland city – during your stay.
Annapolis is a city rich with diversions and Royal Folly’s innkeepers are keen to help craft your itinerary with their knowledgeable suggestions. Sail Chesapeake Bay’s sparkling waters or spend a day indulging in a local day spa – this Maryland inn’s getaway packages even save you the headache of planning ahead. One such offering, fittingly called The Royal Treatment, welcomes you with a bottle of champagne and delectable fruit and cheese platter upon arrival. You’ll even be treated to a tasty token of thanks to take with you, in the form of the Annapolis Bed and Breakfast Association’s very own cookbook. Royal Folly’s rooms and suites come equipped with equally royal names, to say nothing of the distinguished décor housed within each. Four-poster beds and color palettes of rich purple and crimson hues make these some of Annapolis’ most seductive accommodations. And the inn’s adults-only designation makes this a Maryland inn worthy of that romantic weekend you’ve been dreaming of!
65 College Ave., Annapolis, MD 21401
Royal Folly serves a full plated breakfast each morning and a special champagne brunch on Sundays.
The Mistress Erika Suite at Royal Folly is pet-friendly and the inn even offers special Luxury Doggies Getaway packages for discerning pooches.
Our No. 3 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. 3 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.
10568 Cliff Rd., Chestertown, MD 21620
Great Oak Manor partners with Gooseworks Consulting to provide intriguing team building activities for your Maryland meeting or special occasion.
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.
St. Michaels, Maryland
With its brick exterior, intricate porch latticework and storybook steeple, our No. 4 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.
210 N. Talbot St., St. Michaels, MD 21663
Fishing, golf, kayaking, horseback riding, sightseeing and sailing.
The Parsonage Inn is within walking distance of the harbor, and local favorites like the Chesapeake Bay Maritime Museum are just across the street.
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.
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.
Tennis, Bocce ball, croquet, skiing, snow tubing and snowshoeing.
St. Michaels, Maryland
Tucked away just beyond the borders of downtown St. Michaels, our No. 7 pick’s private acreage makes for a peaceful and secluded Maryland vacation. Yet for all its worlds-away appeal, Folly’s Cove Bed and Breakfast is still close enough to enjoy this historic town’s myriad charms.
At Folly’s Cove, the traditional full breakfast – served in the inn’s cozy sunroom and included in your rate – is merely the beginning. Four-poster beds, private baths and intimate sitting areas are highlights of this Maryland inn’s guestrooms and suites, and romance is practically inevitable inside the Queen Anne Room, with its waterfront balcony and cozy fireplace. Take advantage of midweek discounts that add value to your Maryland vacation, or add a dozen roses in honor of your most special occasions. Folly Cove’s gracious innkeepers are more than happy to help you tailor your stay. Just beyond your Folly’s Cove Bed and Breakfast suite, a lakefront pool fed by whimsical fish fountains invites leisurely swims in its sparkling waters. Elaborate gardens, evidence of the innkeeper’s green thumb, add even more color to Folly Cove’s already picturesque grounds. Head out to the private docks, dip your toes in the water or toss a few bread crumbs to Gretta and Ernie, the inn’s resident swans.
24811 Rays Point Rd., St. Michaels, MD 21663
Boating, shopping, antiquing, sightseeing, sailing, horse and buggy rides, museum tours and more.
Take Rte. 50 East toward Easton to Rte. 322 South. Continue about two miles and make a right onto Rte. 33 West. Follow this for seven miles and turn left onto Peaneck Road. Then take a second right onto Rays Point Road and proceed to the third driveway on the left.
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!
112 High St., Cambridge, MD 21613
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.
With its pale yellow exterior, white crown molding and elegant shuttered windows, it’s hard to imagine our No. 9 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.
144 Prince George St., Annapolis, MD 21401
Walking tours, sailboat charters, sunset cruises, sailing lessons, fishing and golf.
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.
This gated Maryland estate, circa 1760, opens up to six beautifully-landscaped acres, and counts the Little Patuxent River’s scenic waters as one of its finer features. If you thought its blooming gardens and bricked patio were exquisite, wait until your eyes behold the Commodore Joshua Barney House’s equally inspired interiors.
The Commodore Suite – easily the inn’s most spacious accommodation, and arguably its most luxurious – pays tribute to the Commodore House’s namesake, Joshua Barney, who valiantly served in both the American Revolution and the War of 1812. High ceilings and original hardwood floors make the bedroom and sitting area a sight to behold, while heated towel racks and a glass-enclosed shower provide the utmost of comfort in the attached bath. You can even brush up on your early American history; this Maryland bed and breakfast offers biographies of its beloved hero and other historic documents for your enjoyment. For those traveling to Maryland in summer, the Commodore Joshua Barney House’s exquisite gardens prove to be the highlight of warm weather getaways. A screened-in gazebo graces the grounds with its charming presence, and steps out to a patio that overlooks the lily pads and lotus flowers of the inn’s own water garden. Just beyond this quaint structure, brick paths lead to even more hidden treasures, including a bridge that spans the Little Patuxent River’s meandering waters.
7912 Savage Guilford Rd., Savage, MD 20763
Commodore Joshua Barney House also offers the Captain’s Quarters, a stand-alone apartment complete with kitchen and home-style comforts, for extended stays or Maryland business trips.
Related Onsite Offerings
Parking, amenities, snacks, beverages and breakfast are included in your rate.