$169 - $459

Brampton Bed and Breakfast Inn Chestertown, Maryland

Chestertown, Maryland

Asking Price: $ / Number of Rooms: 7 rooms 6cottage/s


The Brampton Bed and Breakfast Inn offers guests a romantic setting one mile from historic Chestertown on Maryland's Eastern Shore. This Maryland bed and breakfast is a meticulously restored 1860 manor house featured on the National Register of Historic Places. We are nearby popular shops, waterfront dining, and the Garfield Center for the Arts. Our inn features 13 luxurious accommodation options ranging from rooms, to suites, to a pet-friendly apartment.

What better way to complement your visit to the Chesapeake Bay region than to surround yourself with the beauty of an 19th-century estate on Maryland’s Eastern Shore! All rooms are exceptionally spacious and well-appointed with comfortable furnishings. You will enjoy the park-like view of the landscaped fruit, vegetable and flower gardens surrounding this romantic B&B. An à-la-carte breakfast is served each morning, and afternoon tea between 4 and 5.

$170 - $300

Flag House Inn Annapolis, Maryland

Annapolis, Maryland

Asking Price: $ / Number of Rooms: 5 rooms


Located in the center of Historic Annapolis, Maryland, the Flag House Inn offers on site parking, fresh cooked hot breakfast, king beds, en-suite bathroom, fast wi-fi and all the other modern experience while still retaining the charm of an 1879 built home. It's only 2 blocks to the center of town and all major attractions are within walking distance, including restaurants, shopping and the U.S. Naval Academy. A wonderful destination for a couples retreat or family vacation, the inn combines privacy and the friendliness for the perfect getaway. Let us help you plan a memorable experience!

The Flag House Inn is located in the heart of historic Annapolis, Maryland. The perfect location to visit the many offerings of Annapolis, the inn is only a block away from the waterfront’s City Dock and directly across the street from the U.S. Naval Academy.

Offering free on-site parking, this quiet and romantic getaway is packed with history, comfortable accommodation and upscale amenities. Relax in one of the Flag House Inn’s uniquely decorated guest rooms with period furnishings and plush king beds. (Twin beds/ singles available in two rooms).

Each room has private bath, fast Wi-Fi, HD TV, slumber sound machine and much more. In the mornings a full hot breakfast is served in the guest dining room, which includes fresh fruit, homemade baked goods and “made from scratch” sweet or savory mains. During the day enjoy the content in the guest library, read a book at the fireplace or go out on the porch swing/ benches to catch a breeze and watch the world go by.

Conveniently located to a variety of activities and attractions of the Annapolis area, take a stroll and experience the shops, museums and restaurants of the city. Visit the William Paca House, Hammond-Harwood and Chase Lloyd houses for a little history. Plan an afternoon sailing around the Bay and other maritime activities.

Best of all, once you park your car, you wont need it until it’s time to go home….

$189 - $239

Hummingbird Inn Easton, Maryland

Easton, Maryland

Asking Price: $ / Number of Rooms: 6 rooms


A new B&B experience that's more than just a place to sleep!

Hummingbird Inn is located in a beautiful, circa 1865 Queen Anne Victorian in the heart of Easton, Maryland’s historic district. Blending the best of Victorian style with modern comfort, the Hummingbird Inn is welcoming, hospitable, and so much more than just a place to sleep. We’re a quick, two-block walk from Easton’s boutique shops, restaurants, galleries, and theater, and short a ride to boating, beaches, and all the Eastern Shore attractions. Hosting an Event? Hummingbird Inn’s stately architecture, lush landscape, and extensive Victorian gardens offer a striking, spacious venue Relax, meet new friends, discover the beauty of the Eastern Shore. Hummingbird Inn is a stately Queen Anne Victorian with a striking copper-roofed turret, lush gardens, and wrap-around porch. Hummingbird Inn blends the grandeur of the past with modern features and comfort.

Our common rooms include a guest parlor with fireplace, a game area in the Queen Anne turret, with cards and board games, and a variety of seating areas for socializing or curling up with a book next to the traditional brick hearth fireplace. We have free WiFi throughout the property, or if you feel like checking out the area on bike, you can check out an Inn Bike and go for a ride on tree-lined streets and scenic backroads. Join us in the evening for “Porch Time” on the deep veranda. Relax and enjoy a glass of wine, music from the integrated Bose sound system, and good company in one of several seating areas, or watch the stars come out from the Victorian porch swing. Stroll under the giant magnolia tree and savor the serenity of Hummingbird Inn’s gardens on our ¾ acre of land, with courtyard fountain, hidden benches, and comfortable lounge chairs perfect for a quiet moment, a picnic, or special event. Built in 1865, Hummingbird Inn was fully restored in 2006, with modern plumbing and electrical, including an endless hot water supply and geo-thermal heating/air conditioning Hummingbird Inn’s rooms, the largest among Easton’s historic properties, blend Victorian style with modern comfort, including king or queen pillow-top beds, down comforters and pillows, a sitting area, en suite baths, and plentiful windows with a flood of natural light. Some rooms offer their own working fireplace for a cozy or romantic evening. All guest rooms include private bath with heated towel racks, hair dryers, and eco-friendly soap, shampoo/conditioner, bath salts, and lotion.

Each unique room offers a variety of options – traditional slipper clawfoot tub, bubble-jet tub, rainfall shower head, or tub/shower combination. Of course we provide the modern day essential comforts such as central air/heating, ceiling fans, HEPA filters, WiFi, and cable TV with HBO. Every reservation includes our highly acclaimed three-course breakfast served daily from 8:00 – 10:00 a.m. in the dining room. We also offer guests their choice of entree which includes signature dishes such as Smoked Salmon, Broccoli & Pea Frittata, Crème Brûlée French Toast or a Bacon Wrapped Soufflé. We proudly serve Rise-Up coffee’s, a selection of tea and fruit juices, and if you want a little extra “kick-start” to your morning, have a Mimosa or a Hummingbird Bellini made with Pear Nectar and Cranberry juice.

$175 - $345

Inn at Huntingfield Creek Rock Hall, Maryland

Rock Hall, Maryland

Asking Price: $ / Number of Rooms: 5 rooms 7cottage/s


The Inn at Huntingfield Creek is a well-appointed bed and breakfast situated on 70-acres of land with Chesapeake Bay views. featuring comfortable rooms with fine linens, plush robes and towels, down comforters and private bathrooms. The harmonic atmosphere of the inn is perfect for weddings, family vacations or a romantic retreat with guest rooms, cottages and a vacation rental available for lodging. Enjoy panoramic views of the countryside, pet-friendly rooms, spa baths with whirlpool tubs and much more. Maryland’s Eastern Shore region is well known for its many nature preserves, fishing/crabbing, marinas, antique shops and areas of historical interest. As the Inn at Huntingfield Creek is the closest inn to the wonderful Eastern Neck National Wildlife Refuge, it’s easy to spend an entire day walking the trails, snapping photos or viewing the resident Bald Eagles and tundra swans enjoying the wonders that Chesapeake Bay has to offer.

$160 - $210

Moonlight Bay Inn & Marina Inc Rock Hall, Maryland

Rock Hall, Maryland

Asking Price: $ / Number of Rooms: 10 rooms


Moonlight Bay Inn & Marina is located on the shore of the magnificent Chesapeake Bay in Rock Hall, Maryland. The Queen Anne Victorian inn is elegantly furnished without being stuffy - the atmosphere is warm and friendly. We offer 10 beautiful guestrooms - 5 in the Main Inn, and 5 in the West Wing - all with private baths and water or garden views. We have 50 boat slips on 2 docks at the marina, where guests can enjoy barbecues and a variety of water activities.

Enjoy the park-like ambience of our inn as the soft breezes and playful sea birds provide the soundtrack to your peaceful getaway. Your hosts Dorothy and Robert Santangelo have created a luxurious and welcoming atmosphere for you to enjoy. Come by car, or come by boat!

$189 - $329

Sandaway Waterfront Lodging Oxford, Maryland

Oxford, Maryland

Asking Price: $ / Number of Rooms: 8 rooms 1cottage/s


Sandaway Waterfront Lodging in Oxford, MD is a romantic, tranquil getaway. Sandaway offers 17 bed & breakfast-style accommodations overlooking a private sandy beach on the Eastern Shore of Maryland.

Embark on a Chesapeake Bay getaway at Sandaway in Oxford, Maryland. Sandaway is a member of Select Registry, a collection of some of the best bed and breakfasts, inns, and small hotels. Sandaway is one of the few bed and breakfasts in Maryland with a private sandy beach on the Eastern Shore. From the beach you can see spectacular views of two rivers as they merge into the Chesapeake Bay. An interesting variety of watercraft and waterfowl often pass by Sandaway. Guests love to spend hours relaxing in this tranquil setting. The waterfront Adirondack and lounge chairs are popular seats at Sandaway. For more privacy, most of the B&B rooms provide screened-in porches overlooking the water. Sandaway is close to Saint Michaels, Easton, and Cambridge. A car ferry provides a shortcut to Saint Michaels, just 7 miles away.

$118 - $118

Sinking Springs Herb Farm Elkton, Maryland

Elkton, Maryland

Asking Price: $ / Number of Rooms: 0 rooms


Book your romantic retreat at this historic farm - historic Bed & Breakfast at Sinking Springs Herb Farm in Elkton, Maryland. Enjoy a full breakfast on our sunlit patio, then head out to the Labyrinth Serenity Walk, included in our "Herbs of the Bible" program.

The Historic Sinking Springs Herb Farm & Retreat is set on 130 beautiful rural acres in Elkton, Maryland. Come explore the gardens and hear the history of an 18th-century provincial plantation house. See the ancient sycamore tree which sprouted in 1578. As part of the 2 1/2 hour program, sit down to an herbalicious gourmet delight – a luncheon of fresh, unprocessed food prepared with herbs and served in the original house. Or if you prefer, we also offer a program, “Herbs of the Bible” with a Labyrinth Serenity Walk. Afterward, if you wish, browse the gift shop, which offers herbs and dried flower creations. It’s a perfect secluded getaway – great for honeymooners of all ages! We also offer a private cottage garden for intimate picnics or enjoy a cozy warm fire (also electric heat) to snuggle by. Then relax & enjoy a leisurely breakfast (your choice) surrounded by the beauty of Sinking Springs.

$135 - $250

Solomons Victorian Inn Solomons, Maryland

Solomons, Maryland

Asking Price: $ / Number of Rooms: 3 rooms


Let the Chesapeake romance you at this gracious 1906 Queen Anne Victorian, located on Solomons Island. Nestled on the Western shore of the Chesapeake Bay, Solomons takes you back to a bygone era. Experience the unforgettable views of the harbor from your room or while strolling the lovely gardens

Fall in love all over again. Solomons Victorian Inn captures all the charm and grace of a bygone era. Innkeepers Judith and Robert have created a warm and gracious Maryland getaway, not only making their guests comfortably welcome, but assuring return visits. Whether you are enjoying the harbor views from your room, having a glass of wine in the lush gardens, dining on one of the Inn’s sumptuous breakfasts, or just strolling through the quaint village, the atmosphere that surrounds you will make your stay a lasting memory.

The Inn is situated on the southern tip of Solomons Island, MD along the beautiful western shore of the Chesapeake Bay. This location makes for a truly easy getaway, as it is less than 1 .5 hours from Northern Virginia and Washington, D.C. The Inn is also convenient to Richmond, Baltimore, and Philadelphia for an ideal alternative to Solomons Island, Maryland hotels. Solomons Island is an inviting year-round travel destination. Most restaurants, shops, and the Calvert Marine Museum are open twelve months a year and are only a short stroll from the Inn. The area enjoys sunshine 245 days per year, so there isn’t a time when something is not in bloom – whether camellias in February or crape myrtle in September. Solomons is the perfect location and Solomons Victorian Inn, the perfect choice, for your Maryland getaway.

$$235 - $$600

The Inn at Tusculum Farm LAYTONSVILLE, Maryland

LAYTONSVILLE, Maryland

Asking Price: $ / Number of Rooms: 6 rooms


Helping People Celebrate Life

Whether you’re looking for an escape from your everyday, enjoying time with family and friends, or something in between, The Inn at Tusculum Farm offers the perfect array of accommodations to meet your desires and needs. This is luxury farm living at its finest, with best in class rooms, amenities and overall service.

Tusculum Farm, historically known as Sundown Farms*, is included in the Maryland Inventory of Historic Properties and has a rich American history. The property was owned in the mid-18th century by Henry Griffith, a prominent Marylander who in addition to being a member of the Annapolis Convention that formed the Association of Freeman of Maryland, also witnessed the signing of the Declaration of Independence. Carl and Virginia Freeman became the owners of Tusculum Farm in May of 1964, making them the 16th in the chain of titles of the 500+ acre property dating back to 1747.

Virginia Freeman, who lived on the farm for the remainder of her life (1964-2012), used to say that “fairies lived in the woods” at Tusculum. That is the magic of the family farm, and that magic is something we have all discovered in our own way here. The mix of history, connection with the land, and the discovery of something new every time you visit is what makes this farm unique.

Aside from the gorgeous views and the historic structures and stables, there are also incredible personal touches to the farm that have been contributed by the Freeman family over the years. Virginia Freeman loved and planted flowers – red poppies can be seen around the farm as a representation of her love of Florence, Italy. There is a “Gertrude Stein Garden” because Virginia Freeman considered herself a poet and artist, as well as a remarkable collection of sculptures collected by Carl and Virginia Freeman that appear throughout the property.