Uncover the Charm of Maryland’s Historic Hotels

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Step back in time and experience the timeless allure of Maryland’s historic hotels. Discover the perfect blend of history and luxury.

The elegant hotel situated by the water seems untouched by the hands of time. Countless guests have passed through these doors, some famous, some forgotten in the sands of time. I loved exploring small towns in the Mid-Atlantic states and staying at Maryland’s historic hotels, inns, and taverns. These places are interesting, and some are reputed to have ghosts; all have stories to tell.

With 15 years of extensive travels in Maryland, I invite you to come along for a trip into hospitality history as I share with you some of my favorite lodging establishments. This collection is from small towns I have visited and fell under their spell.

Maryland’s Eastern Shore

The Eastern Shore of Maryland has a deep history of over three hundred years since white Europeans arrived. Sadly, little remains of the flourishing native culture that the newcomers pushed out, but plenty is still evident from colonial times. The tale of Thomas Savage, a lad of 13 who arrived in Jamestown in 1608, is one of my favorite stories. Young Thomas was sent to live with the Native Americans to learn their Algonquin language and customs. Some years later, Laughing Chief gave him 9,000 acres in Accomac, and a few of Savage’s descendants still live there.

About an hour’s drive from where Thomas Savage settled is one of my favorite vintage hotels. The Whitehaven Hotel in Quantico, MD, was built in 1810 and has stayed in business for over two centuries. The current owners undertook massive renovations to make it a pleasant place to stay.

I enjoyed the breakfast at the Whitehaven Hotel. Photo by Kurt Jacobson

A River View

The Wicomico River flows by in front of the hotel and features one of the longest-running ferries in the country, which provides service across the river. Guests come for the peace and quiet or to explore the country roads by bicycle, car, or on foot. Take your pick from eight rooms, one of which is dog-friendly, and all room rates include a hearty breakfast.  We loved taking our German Shepherd along to enjoy hikes on quiet roads. Fishing and birding are popular pursuits near the Whitehaven Hotel, and I enjoyed watching the osprey.

An osprey watches over the Wicomico River Ferry. Photo by Kurt Jacobson

A Town With Two Historic Hotels

With several excellent shops, restaurants, and a Rails-to-Trails path for hiking, Easton ticks many boxes on a travel destination. Easton has two historic places to stay that we’ve enjoyed. The Hummingbird Inn was built in 1887 and has been a B&B under the watchful eye of Eric Levinson since 2017. What we love about the Hummingbird Inn is how easy it is to walk into downtown Easton. Each room is decorated uniquely in period fashion, except for the Crisfield room on the third floor, which is contemporary Zen decor.

The Hummingbird Inn is one of Easton’s best places to stay. Photo by Kurt Jacobson

The Hummingbird Inn is a dog-friendly B&B but charges a $25 per night pet fee. When we take our dog, we love that Eric will dog-sit for a reasonable rate of $15 per hour while we go out for dinner. Another thing we like about staying at the Hummingbird Inn is the nearby 2.5-mile Rails-to-Trails path, which is good for a pleasant walk for pets and humans.

Downtown Easton

Another Easton hotel we like is The Tidewater Inn, circa 1891. The original hotel burned down in 1944, was rebuilt, and the current version is going strong. With 86 rooms to choose from, take your pick of an affordable premier guest room or a premier king suite. We like that The Tidewater Inn is dog-friendly and offers AARP or AAA discounts. Hunters Tavern at the Tidewater Inn is a popular bar and restaurant for locals and visitors. If you plan on coming to the Waterfowl Festival, book your stay at least six months ahead of time for either of these Inns.

Staying at the Tidewater Inn puts guests in the middle of town and close to excellent restaurants. Photo by Kurt Jacobson

Further Up the Shore

Chestertown is another Eastern Shore town with two great historic inns. For an in-town stay, the White Swan Tavern is a great choice. The Inn is in excellent condition. This restored colonial-era Inn was built in 1730 and updated in 2023. Innkeeper Beth Lavery told me, “We have renewed our commitment to a superior guest experience with a delicious breakfast, comfortable beds in a beautiful building, and a friendly, knowledgeable staff.”

The Lovegrove room is where the old kitchen from Colonial times was located. Photo by Pamela Cowart-Rickman

With only six guestrooms at the Inn, be sure to book well in advance to get the room of your choice. The Lovegrove room would be my first choice, as it once served as the kitchen. Special events like Downrigging Days see rooms booked many months in advance, and some return guests book their rooms a year in advance to ensure they aren’t disappointed.

Enjoy a home-cooked breakfast as part of your stay.  Photo by Pamela Cowart-Rickman

There is free guest parking out back, a delicious full breakfast, walking distance to most everything in Chestertown, and it’s in a great location. Don’t miss Evergrain Bakery, a from-scratch spot for excellent baked goods like sun buns, everknots, croissants, buzz bars, and bread.

An Elegant Country Inn

Brampton Inn on the outskirts of Chestertown is a stately Victorian home from 1860. Under the loving care of the new owners, Dave and Hilari Rinehart, Brampton has become a great place to stay. Set amongst native trees and formal gardens, guests love strolling the 35 acres.

On each of my two visits to Brampton Inn, I stayed in the Yellow Room and loved it. Photo by Kurt Jacobson

Choose from cottages, suites, or main house rooms for your perfect stay. All accommodations include a full breakfast, use of the parlor rooms, outdoor fire pits, and plenty of free parking. Cottages are pet-friendly, but not the main house rooms. Brampton is known for holding special events such as weddings, family reunions, and seasonal dinners on the new patio.

I attended a special Fall-themed dinner at Brampton and loved the food and atmosphere. Photo by Kurt Jacobson

St. Michaels

The Inn at Perry Cabin is famous for its luxurious grounds and upscale lodgings. What started as a private home built in the early 1800s has become a fine place to stay and play. With a waterfront location, the Inn at Perry Cabin often has guests who arrive by sailboat. Paddleboards or kayaks are available for guests to enjoy the calm waters near the Inn. You can enroll in sailing instructions on one of several sailboats owned by the Inn.

A pair of kayakers enjoy a peaceful afternoon on the water by the Inn at Perry Cabin. Photo by Kurt Jacobson

Special events, especially weddings, bring many guests to the Inn. Tennis courts, golf, and croquet are fun ways to spend your time. As for the lodgings, choose from guest rooms or suites. Off-season rates offer significant savings over late spring and summer rates. Depending on the season, an onsite restaurant named Stars is available for lunch or dinner most days and breakfast on weekends. The town of St. Michaels has plenty of good dining choices as well.

The Inn at Perry Cabin is the most luxurious lodging I’ve experienced on the Eastern Shore. Photo by Kurt Jacobson


The tiny town of Oxford is just minutes as the crow flies from St. Michaels but takes about 30 minutes to drive. The Robert Morris Inn claims to be the oldest full-service Inn in America. This historic Inn started as the River View House in 1710 and is one of the more historic inns I’ve visited. The namesake, Robert Morris, was a wealthy merchant who helped finance the American Revolution.

A stay at the Robert Morris Inn in Oxford is a memorable event. Photo by Kurt Jacobson

Four of the inn’s rooms are in the old part of the building and are bursting with character. The floors squeak when you walk on them, telling tales of visitors from long ago if you listen with your imagination instead of just your ears.

The restaurant is a great place to grab a delicious meal and feel like you’ve stepped back in time some 250 years. Consider riding the historic Oxford-Bellvue Ferry, established in 1683. If you bring your bikes, you can ride the ferry across to Bellvue and pedal to St. Michaels. Note that the ferry doesn’t operate in the winter.

After a superb dinner at Salter’s Tavern in the Robert Morris Inn, I felt like a wealthy merchant from Colonial times. Photo by Kurt Jacobson

Just Because

I’ve visited Berlin, MD, twice. On each visit, I’ve gone into the Hotel Atlantic, circa 1895, but never spent the night. The hotel has 15 guest rooms, one cottage, a large full-service suite, and a restaurant.

The Atlantic Hotel in Berlin looks worthy of a future stay. Photo by Kurt Jacobson

I recommend this hotel just because it’s a looker! Because it is situated in the town center, walking to all the cute shops, restaurants, and bakeries is easy. I hope to stay in the Atlantic Hotel on one of my future trips to the Eastern Shore to see how it rates with the other historic lodgings on my list.

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Checking Out

I hope you enjoy Maryland’s historic small-town hotels as much as I have. There are several to choose from, each offering a unique experience you won’t get when staying at a modern corporate hotel. I recommend contacting the hotels ahead of time to see what special events might be going on to add to your enjoyable stay. We invite you to explore Wander With Wonder for more to do when you visit Maryland and more of our favorite hotels and resorts around the world or across the street.