Bed and Breakfast Annapolis MD

Annapolis, Maryland, a vibrant city on the Chesapeake Bay features a bustling waterfront, well-preserved examples of historic architecture and plenty of exciting things to do.

Bed and Breakfast Annapolis MD

Laurel Grove is a luxury Bed and Breakfast in Annapolis, MD. It is an 8,400 sq. ft. cedar and stone contemporary home on three acres overlooking the South River.

Georgian House Bed & Breakfast is located in the heart of the Historic District of Annapolis, Maryland. Experience true colonial elegance in this 1747 house that was once used as a meeting place for 3 signers of the Declaration of Independence. The house is beautifully constructed and features 16-inch brick walls to ensure peace and quiet. Our four guestrooms combine old-world charm with modern conveniences like private baths, TV, and WiFi.

The Annapolis Inn Bed & Breakfast is in a prime location on stately Prince George Street in the Historic District of Annapolis. The inn is surrounded by elegant mansions and is just steps away from the U.S. Naval Academy, St. John's College, the City Dock, the Maryland State House, and so much more. There's no need for a car, just comfortable walking shoes!

The Scotlaur Inn Bed & Breakfast is located in Annapolis: the heart of Maryland, and the Sailing Capital of the World." You'll enjoy the rich heritage of Historic Annapolis and the pleasant scenery of the Chesapeake Bay. Located near everything you need for business or pleasure."

Enjoy sunny-colonial comfort at the Annapolitan bed & breakfast located in Annapolis, MD. Centrally located near downtown historic Annapolis, take a step back in time and enjoy the wonders that our area has to offer.

Chez Amis Bed & Breakfast is an intimate, friendly B&B with a charming ambience. We offer 4 romantic guestrooms with luxurious private baths, cable TV & DVD, central air, and free WiFi. Located in the heart of historic Annapolis, Maryland, the inn is just steps from the State Capitol, St. John's College, City Dock, the U.S. Naval Academy, antique shops, and fabulous dining.

This Annapolis, MD bed and breakfast offers luxurious rooms and accommodations in Maryland. Book your stay today! Click our link above to Book Direct for your next getaway in Annapolis, MD.

Offers seclusion, while allowing easy access to many activities, Peninsula House is located in the maritime district called Eastport, just a short walk past all the best waterfront resturants to city dock and main street shops.

Our ultimate goal is uncompromising service in an atmosphere of personal hospitality.

The Flag House Inn is located in the heart of historic Annapolis, Maryland. The perfect location to visit downtown 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 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 Banneker-Douglass 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….

In the heart of the historic district, Gatehouse of Annapolis Bed & Breakfast overlooks the US Naval Academy. From our convenient location you can walk to St. John's College, and City Docks... The Gatehouse of Annapolis is a classic Georgian-style townhouse that has been lovingly refurbished to provide guests with an atmosphere of comfortable elegance The Gatehouse of Annapolis is an oasis for the connoisseur of travel.

The best location in Annapolis! Welcome to Gibson's Lodging's of Annapolis--an Inn located in the heart of the Annapolis Historic District & 1 block from the city dock and many great restaurants. Park your car in our courtyard and walk to everything!

Exceptional bed and breakfast hospitality awaits you in the comfort of this gracefully restored 1908 cedar shake shingle home. The William Page Inn offers peerless accommodations to its guests.

Nearby Properties


$299.00 - $399.00

Annapolis, MD, USA

Embark on a Chesapeake Bay getaway at Sandaway Suites & Beach in Oxford, Maryland. Easily walk to restaurants and shops in the historic district. Sandaway is a member of the TripAdvisor Hall of Fame and one of the few boutique hotels 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 boutique hotel rooms and suites provide screened-in porches overlooking the water. Sandaway is close to Saint Michaels, Easton, and Cambridge. A car ferry provides a shortcut to St. Michaels just 7 miles away.

A warm welcome to The Robert Morris Inn and Salter's Tavern, arguably America's oldest operating Inn. This historic building originates from 1710 and celebrates its 300th Anniversary this year. Once the home to Robert Morris Sr. and his son who gained fame as Financier of the Revolution"

Two centuries of history await you at The Wilderness; historic preservation and hospitality award winning B&B providing suites for discriminating guests. Surrounded by woodland tracts of The Patapsco Valley State Park, this Victorian era summer mansion has been restored to its country manor atmosphere, and offers unequalled peace and privacy. Spacious suites, comfy beds, fabulous baked goods and nearly total seclusion give guests the sense of being “away from it all” although only minutes from historic Ellicott City and Catonsville, and only 15 minutes from Baltimore’s Inner Harbor/BWI airport.

Next to the harbor and the Chesapeake Bay Maritime Museum, just two blocks from the main street of St. Michaels.

The 1840's Carrollton Inn Bed and Breakfast in Baltimore, MD is only four blocks from the Inner Harbor and walking distance to over 20 museums and cultural attractions.

Welcome to Victoria's Gardens Inn Bed & Breakfast a distinctive Victorian getaway located in historic Cambridge, Maryland.

Welcome to Lodgecliffe on the Choptank, Cambridge's only water front bed and breakfast. Lodgecliffe is a gracious turn-of-the-century country home perched on a bluff overlooking the water. We invite you to experience the delight, charm, romance and relaxation that is Lodgecliffe.

The Wilson House Bed & Breakfast in Baltimore, MD is close to the Mt Vernon Cultural District, with easy access to the opera, symphony, Johns Hopkins University, Maryland Institute College of Art, the University of Baltimore and many interesting restaurants. Wilson House has 40+ rooms, with twin parlors, eight fireplaces, ten bedrooms, numerous original chandeliers, a library, a den with sunroom, and 9+ baths.

Welcome to the Inn at 2920; A downtown Baltimore inn with a distinctively contemporary style. Leisure and business travelers enjoy comfortable guest rooms with flat screen HDTV’s, private limestone bathrooms, free Wi-Fi and sumptuous full breakfasts. Inn at 2920's location offers easy access to all of Baltimore's attractions by foot, by car, or by the Water Taxi on the Harbor just two blocks away.

Situated 12 blocks from the White House, our location in the historic Dupont Circle neighborhood makes Swann House Bed & Breakfast the ideal home base for your visit to Washington, DC. Also our proximity to several universities makes Swann House convenient for parents visiting students.

Carefree Elegance on the Chesapeake Bay on Maryland's Eastern Shore, Great Oak Manor is a magnificent Georgian Mansion sitting on the banks of the Bay. The beautiful lawns and landscaping create openness while remaining private. Our B&B has 12 guest rooms and a spacious Carriage House that is perfect for families. Our private beach allows our canoe, kayaks and paddle boards easy access to the water. Take our cruiser bicycles out for a ride on our flat country roads or choose to relax in our Adirondacks by the water or nap in one of the hammocks. Our evening sunsets are not to be missed!

Welcome to the Bay Breeze Inn in Rock Hall, MD dating back from the 1920's and was a favorite with Eastern Shore goose hunters who stayed at the Old Crosby Property"."

Perfect for hosting weddings, special events, and romantic escapes, The Combsberry Bed & Breakfast, is an 18th century English country manor on Maryland's scenic Eastern Shore. Nestled on 35-acres of beautiful land, in the heart of Oxford, you can enjoy a number of activities like the Oxford Museum, take a ride on the Bellevue Ferry, enjoy activities at the Waterfowl Festival in Easton, or take in the sights at the Blackwater National Wildlife Refuge in Cambridge.

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.

Located on Maryland's Eastern Shore of the Chesapeake Bay between St. Michaels and Tilghman Island. Come join us in our island like setting and watch our spectacular sunsets. Offering waterfront guest rooms, restaurant, patio bar, marina, charter fishing, sunset cruises, crabbing, kayaking, or just sitting back on our private beach watching the sunset.

Explore Bed and Breakfasts in Annapolis MD

The state’s capital city thrived in the 1600s and 1700s leaving  behind a number of historic homes and buildings. As such, the city has a  vibrant and colorful historic district with shopping and dining options along the waterfront. Annapolis is within easy reach of Baltimore and Washington DC, so day trips to both cities are quite possible. Annapolis is perhaps best known as the home of the U.S. Naval Academy.  The Academy draws many visitors to the area each year.  Many of the  city’s historic buildings have been converted to shops, restaurants and bed and breakfasts.
There are a number of bed and breakfasts near Annapolis MD. If you are looking for a nice place to stay for your visit, an Annapolis Bed and Breakfast is a fantastic option. Choose from enviable downtown locations, properties with waterfront views, and a pet friendly bed and breakfast in  the Annapolis historic district. There’s truly something for everyone. Read on for more information about booking a bed and breakfast for your next trip to Annapolis.


  • Annapolis was originally settled in 1649 by Puritan exiles who had fled Virginia.  The town had several names throughout history including Anne Arundel Town and Providence. It was given the name Annapolis in 1694 after Princess Anne, heir to the British throne. In the  post-Revolutionary period, several important historical events happened  in Annapolis including meetings of Congress and Washington’s resignation for his  place as commander of the Continental army. Many significant historic  buildings are located throughout Annapolis including the Maryland State House, St. Johns College, and the William Paca House and Garden. Visitors can learn more about Annapolis’ history at these sites and museums throughout town.

  • Things to do

  • There are a number of fun things to do when visiting Annapolis. Downtown Annapolis is always bustling with activity and ripe for sightseeing. Take a walk along the Annapolis waterfront and admire the boats at the city dock. Alternatively, go sailing on the Chesapeake Bay for a look at the city from a different point of view. Both the U.S. Naval Academy and St. John’s College are located near downtown and the waterfront, so visitors will find  plenty to do within a short walk. The Naval Academy has its own museum,  the Academy Naval Museum. You’ll also find the Annapolis Maritime Museum, the William Paca House and Gardens and Hammond-Harwood House within easy reach of many of the bed and breakfasts in Annapolis, MD.

  • Weather

  • The best time to visit Annapolis, MD is during the spring when the weather is mild, the trees blossoming and the sailing season is just getting its start. However, Annapolis is a 4-season destination with something to offer any time of year. In  the summer, temperatures are warm, but not too hot and the harbor area  is bustling with activity. In fall, the weather turns cooler, but the  changing colors of the leaves make a wonderful backdrop for exploring Annapolis.  In winter, temperatures get quite cold, but there are still plenty of  things to do inside, so a visit isn’t out of the question.

  • Activities

  • Annapolis has been called the ‘Sailing Capital of the United States.’  While visiting the city, you should certainly try to go sailing. Book a sailing tour around the Chesapeake Bay. There are public and private tours available on a variety of boats that are moored at the city dock. Cruises typically offer views of the U.S. Naval Academy, the Annapolis Waterfront, Thomas Point Lighthouse and scenic views of the Annapolis Skyline.

    When you are ready for some sightseeing, head to the historic district. There, you’ll find a number of interesting things to do and see. The Maryland State House, dating from 1779, offers tours to the public. It was the first peacetime capitol of the United States and is the oldest state house that is still in legislative use to this  day. The state house is located near the beautiful campus of St. John’s College and not far from the Annapolis waterfront.

    Family travelers will find plenty of fun kid-friendly activities such as the Chesapeake Children’s Museum, Quiet Waters Park and Sandy Point State Park.

    Being home to the U.S. Naval Academy, the state capitol and St. Johns College, there’s often exciting events being held in Annapolis. Check out the Annapolis Crab Feast, the Annapolis Maritime Festival, St. Patrick’s Day, and the annual New Year's Eve Celebration and Fireworks among others.

  • Natural Features

  • Annapolis, Maryland sits on the Chesapeake Bay at the mouth of the Severn River, about halfway between Washington DC and Baltimore, Maryland. The city has a long maritime history which you can experience by getting out on the Chesapeake Bay on a schooner or other type of vessel. Sandy Point State Park sits at the western end of the Chesapeake bay Bridge and features a very popular swimming beach, a lighthouse and a historic farmhouse. Other beaches dot the shoreline near Annapolis,  including Carrs Beach, Highland Beach, and Bay Ridge Beach. During a  warm summer day, relaxing on the beach and watching the boats on the bay  is a delightful pastime.

  • Food and Drink

  • When thinking about Maryland’s food scene, crab probably comes to mind. Blue crab generously seasoned with Old Bay is one of the most iconic dishes in Maryland. Every type of crab dish can be found at restaurants around Annapolis. From steamed crab to crab cakes, crab soup and even crab pizza, you’ll find many ways to try the famous ingredient. Annapolis has a lively nightlife scene and with it, a number of fabulous bars. If you want to try a signature Maryland drink, try a Margarita seasoned with Old Bay or the Crab Cod. It’s a unique mix of crab juice with rum and cherry flavoring.

Bed and Breakfast Annapolis MD FAQ

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  • What Are the Different Types of B&Bs in Annapolis MD?

    There are a number of wonderful bed and breakfasts in Annapolis. Reynolds Tavern Bed and Breakfast occupies a Georgian mansion in a prime location on Church Circle. The inn is conveniently located near the historic district, dining, shopping and the U.S. Naval Academy.  The property has three overnight rooms and a pub in the cellar as well  as a spacious outdoor beer garden where events are often held.

    The Flag House Inn is one of the best Annapolis bed and breakfasts near the Naval Academy. It’s just across the street but offers a quiet  place to relax with private, on-site parking, comfortable guest rooms, period furnishings and upscale amenities.

    Laurel Grove Inn on the South River is one of the best waterfront bed and breakfasts in Annapolis.  The luxury 8400 square foot cedar and stone home has contemporary  furnishings and sits on three wooded acres with views of the river.

    If you are looking for a pet friendly bed and breakfast in Annapolis, you might consider the State House Inn. The inn is located just across from the State House with easy access to the historic district and the Annapolis waterfront.

  • How can I get around Annapolis MD?

    Baltimore-Washington International Airport (BWI) is approximately 30 minutes by car from Annapolis. Many major air carriers fly to the airport. MTA Maryland offers commuter bus service from Washington DC to Annapolis in the morning and afternoon/evening. There is another line that goes from Annapolis to downtown Baltimore. There is a public city dock and several private docks where those traveling by boat can park. Once you’ve arrived in Annapolis,  it’s possible to get around the downtown harbor area on foot. However,  visitors may want a private car to visit other places in the area.  Rental cars are available at the airport.

  • Why Stay at a Bed & Breakfast in Annapolis MD?

    There are many reasons why staying at a Bed and Breakfast in Annapolis, MD is the best choice when booking vacation rentals for Annapolis. Bed and breakfasts are often located in historic homes with unique, charming interiors and period furnishings. WIth close proximity to the U.S. Naval Academy, the Chesapeake Bay and the historic district, bed and breakfasts in Annapolis are perfectly placed for sightseeing. When you check-in, friendly hosts will be available to help you to your guest room.  They are also willing to help you sort out your plans while visiting or  give you directions to different sights around town. Whether you’re  looking to take a walk around the city dock at the Annapolis Waterfront or are visiting St. John’s College or the naval academy, they’ll be quick to get you on your way.

  • What type of amenities can I expect when booking a Bed and Breakfast Annapolis MD?

    Bed and breakfasts in Annapolis offer many amenities to make your Annapolis getaway comfortable and relaxing. Most bed and breakfasts in Annapolis will have free wifi in the guest rooms and common areas. Air conditioning is common as are private baths and  dedicated dining rooms. Each morning, you’ll enjoy a full breakfast  crafted from local ingredients. Unlike some other types of vacation rentals, bed and breakfasts in Annapolis offer a personal touch that will make your vacation truly memorable.  Specific policies vary by individual property. It’s recommended to check  with each property for information on cancellation, handicap accessibility and parking.