Maryland may be small, but it delivers big on charm, blending Chesapeake Bay’s serene waterfront with Baltimore’s vibrant city buzz. Baltimore’s Inner Harbour brims with luxury and design hotels perfect for groups or stylish getaways, while the Eastern Shore offers relaxed inns and family-friendly stays with coastal views. For budget-conscious travellers, Annapolis provides welcoming, affordable options. From chic city pads to peaceful retreats, Maryland’s hotels cater to every traveller seeking the right balance of comfort, style, and setting.

Some of our Maryland Collections:

• Best Bed and Breakfasts in Maryland

In Baltimore you’ll find a vibrant arts and foodie scene, while nearby Annapolis charms with its colonial streets and lively waterfront — perfect for both history buffs and sailing enthusiasts. For a more laid-back Chesapeake Bay experience, St. Michaels offers quiet inlets, wetlands, fishing, and boating in a picture-perfect setting. Beyond the towns, Maryland is made for road trips, with scenic countryside dotted with cosy inns, hiking and cycling trails, and plenty of opportunities to get out on the water. Civil War sites like Antietam and nearby Gettysburg appeal to history lovers, while foodies will be spoiled by fresh seasonal produce and local seafood. Whether you’re here with family, friends, or on a romantic getaway, the warm welcome and colourful spring blossoms or autumn leaves make it a destination worth savouring year-round.

The Best Places to Stay in Maryland

For a Heritage Inn

• Rachael's Dowry is an intimate six-bedroom inn — once the residence of a prominent American family. Guestrooms feature period furnishings, fireplaces and free-standing tubs, whilst there are delicious breakfasts served in the leafy courtyard. Perfectly placed for exploring Baltimore. For tranquil couples or families with older children.
• Brampton Inn is an indulgent choice, set within an imposing red brick building and a collection of private cottages on 35 acres of grounds, just a mile outside Chestertown. Pick this place for the historic interiors, the crackling fireplaces and big gourmet breakfasts. Great for couples looking to unwind or enjoy the great outdoors.
• Hummingbird Inn offers comfortable bedrooms in a Victorian residence in Easton. Ideal for exploring the Eastern Shore, this owner-run B&B is also dog friendly. Children can be accommodated on sofa beds in some rooms. Small and relaxed.
• Historic Inns of Annapolis is a collection of three townhouses in central Annapolis, featuring opulent rooms behind characterful Victorian façades. You're perfectly placed to see Maryland's historic treasures, plus the onsite bars and eateries are lovely. For families, couples and business travellers. Great for weddings!
• Great Oak Manor has 12 pretty guestrooms and a carriage house — which sleeps 6 — not far from charming Chestertown on the Eastern Shore. Great for couples, groups or families with older children, this elegant Georgian inn offers easy access to walking and cycling trails, as well as kayaking and paddle boarding. The nearby marina has a swimming pool, fitness centre, and nine-hole golf course.

For Civil War History

• Georges on York offers five quirky rooms mixing antique pieces with modern furnishings in an historic building in Taneytown. Close to the Pennsylvania border, this is a great base for exploring Civil War battlefields. An elegant B&B.
• Jacob Rohrbach Inn promises an historic stay within walking distance of Antietam Battlefield, as well as numerous national parks, including the Appalachian Trail. Borrow a bicycle to explore the area on two wheels after hearty homemade breakfasts. An ideal base for history buffs.
• Antrim 1844 is a heritage hotel in Taneytown, just 15 minutes' drive from Gettysburg. Set on 25 acres at the foot of the Catoctin Mountains, this is a beautiful choice for weddings, events and romantic getaways. Interiors feature antique pieces and there is a fantastic restaurant. Civil War battlefields and memorials are within easy reach.

For City Style

• Graduate Annapolis is a funky city hotel with trendy rooms and suites clad in bold primary colours and bright, patterned textiles. Communal areas are centred around a light-filled atrium, and the feel is fresh, comtemporary and very cool. For hip couples, families or business travellers, who can all enjoy the coffee bar, eatery, gym, dog park and bicycles.
• Hotel Monaco is a 1906 Beaux-Arts gem, complete with a marble staircase and sophisticated rooms, in the heart of downtown Baltimore. Pick this place for the delightful brasserie and the sociable wine hour each evening. An historic hotel with a trendy modern twist.
• Hotel Indigo is a cool, contemporary downtown hotel in Baltimore's attractive Mount Vernon neighbourhood. Think stylish rooms with bold pops of colour, delectable fare in the trendy restaurant-bar, and a library, gym and business centre. Sample the hotel's homemade honey whilst there! A stylish, central stay.
• Hotel Revival oozes an artsy, retro feel, with quirky interiors giving a 1920s mansion in Baltimore's central Mount Vernon a new lease of life. Great for groups of friends or romantic couples, the property also boasts beautiful views from its lively bar and eatery. Funky, fresh and fun.

For Waterfront Views in the City

• The Sagamore Pendry is a cutting-edge waterfront pick for hip travellers looking to kick back in sophisticated, modern rooms with warm, rich tones and an emphasis on natural materials. Take a dip in the pool, enjoy a big brunch or BBQ, hit the gym or the spa before savouring a whisky in The Cannon Room. A top-notch Baltimore base.
• Annapolis Waterfront Hotel promises stunning harbour views from slick, contemporary rooms and suites with blue-and-white interiors. A stylish city pick in the historic downtown area, boasting a fabulous harbourfront restaurant. For business or romance.
• The Admiral Fell Inn is a charming choice for those eager to experience the riverside Baltimore of a bygone era. Expect 18th-century furnishings, a lovely waterfront events space and generous breakfasts. The property's signature ghost tours and boat trips are a quirky addition to any Baltimore stay!
• The Inn at Handerson's Wharf features exposed brickwork and 38 comfortable, classic rooms with private terraces in a converted tobacco factory. Stay here for waterfront views, old-school charm and a real sense of history. Baltimore's Fells Point neighbourhood is great for a stroll. For couples, groups or families.

For Couples

• Wade’s Point Inn on the Bay promises a tranquil escape, 10 minutes' drive from St Michaels. Four elegant heritage buildings house 26 generous guestrooms with expansive views over Chesapeake Bay. There are complimentary kayaks, paddleboards, fishing rods and bikes for exploring, and sunsets from the lawn are glorious. Secluded, romantic and relaxing.
• The Inn at Huntingfield Creek is a 70-acre farm estate on the water's edge in Rock Hall. Chic rooms and cottages are ideal for a couples' escape, although there are also family-friendly spaces. Great for active travellers and history buffs, this is also a wonderful wedding venue.
• Sandaway Waterfront Lodging is an elegant Oxford hotel for couples, with spectacular views of Chesapeake Bay. The private beach is the perfect spot for sunset, and the atmosphere is tranquil and romantic.
• Lake Pointe Inn offers an adults-only stay on the edge of Deep Creek Lake. Pick this place for the quiet vibe, the many activities, the spa tubs and the excellent massages. A brilliant B&B for nature-loving couples.

For Outdoorsy Families or Groups

• Savage River Lodge has a collection of yurts and cabins surrounded by 700 acres of spectacular State Forest. Pick this place for a memorable retreat with family and friends. Think wooden beams and crackling fireplaces with luxurious touches, superb cuisine, and heaps of activities including cycling, hiking, geocaching, and wildlife-spotting. A nature lover's dream.
• The Inn at Perry Cabin sits on the edge of the Miles River in St Michaels, featuring beautifully-appointed rooms and suites clad in soothing tones. Expect a spa, an outdoor swimming pool, tennis courts, a sailing school and complimentary bicycles — plenty for active guests of all ages. There's a delectable eatery and many rooms have waterfront views. For adventurous couples, friends or families.
• Wylder Tilghman Island offers a fun, waterfront stay for active couples, friends or families on 3-mile Tilghman Island. Unwind in white and blue bedrooms, spend your days in the saltwater pool, at the bocce court or playing lawn games after bike rides and kayaking trips. The food is fabulous. A 9-acre resort on Chesapeake Bay.

For Luxury

• The Ivy offers just 18 elegant rooms and suites in downtown Baltimore, perfect for an intimate couples' stay, or for a trip with friends and family. Built in 1889 as a private residence, the property now features whimsical interiors and an excellent fine-dining restaurant, Magdalena. Enchanting.
• Four Seasons Baltimore is a glitzy waterfront hotel with dazzling river views from sumptuous contemporary rooms, the outdoor pools, multiple eateries and the indulgent spa. Ideal for business travellers, couples or families looking to unwind in style.

For Great Value

• The Inn at Osprey Point is a well-priced pick for a holiday as a couple or with family and friends. Set on the shores of Swan Creek in Rock Hall, the inn has a large marina, a popular eatery and flexible accommodation options. A good base for Chesapeake Bay activities.
• Hotel RL Baltimore is a centrally-located harbour hotel in Baltimore. Rooms are airy and simple, there are sociable communal areas, and the vibe is very relaxed. An affordable city choice. Free bike rentals are a bonus!

For a holiday house or apartment

• If you'd prefer a self-catering option, we suggest that you visit our online partner Booking.com.

Travel information

• Fly to Baltimore–Washington International Airport, and travel to your destination by bus or taxi.
• Maryland is great for a road trip! If you would like to hire a car, we suggest that you contact our online partner Rentalcars.
• Visit between March and May for the beginning of the sailing season, and to see the landscape in full bloom. The summers are especially busy. Autumn (October - November) is beautiful and winters are cold but cosy!

Still not sure?

• Refine your search to see the best places to stay in Annapolis,
• Alternatively, explore our recommendations for the best places to stay in Washington DC,
• Or contact one of our friendly Gurus for personalised advice.