Romantic Fall & Winter Getaways in Maryland

Location:

Chestertown, MD

Highlights:

If you're dreaming of a peaceful escape with a side of charm and nature, Brampton Inn is just the place. Just a mile from historic Chestertown, this romantic hideaway is a favorite for birdwatchers, bikers, and anyone craving Chesapeake calm.

We Recommend This For:

Couples, birders, art and culture lovers, and anyone looking for a quiet luxury retreat on Maryland’s Eastern Shore.

What we Love:

Secluded cottages, a top birding location, access to kayaking and biking, and proximity to Chestertown’s historic district.

• Stay in elegant guest rooms or private cottages, all with en-suite bathrooms and peaceful privacy.
• Explore the surrounding Chesapeake region by bike or kayak, or wander into charming Chestertown’s arts and entertainment district.
• Discover local attractions like the Garfield Center for the Arts and nearby Washington College.
• Birdwatch in one of the best ornithological spots in the country, right from the property or nearby trails.

Address:

Brampton Inn, 25227 Chestertown Road, Chestertown, MD 21620
Phone: 410-778-1860

Location:

Annapolis, MD

Highlights:

If you want to stay steps from history, dining, and the waterfront, Flag House Inn puts it all at your doorstep. With warm hospitality and Annapolis charm, it’s perfect for exploring Maryland’s capital on foot.

We Recommend This For:

History lovers, couples, U.S. Naval Academy visitors, and travelers seeking a walkable, cultural getaway in downtown Annapolis.

What we Love:

Home-cooked breakfasts, king-size beds, personalized guest recommendations, and unbeatable proximity to top Annapolis attractions.

• Stay in comfortable rooms with private bathrooms, plush king-size beds, and thoughtful touches to make you feel at home.
• Walk to the U.S. Naval Academy, Maryland State House, the waterfront, and historic homes like the William Paca and Hammond-Harwood Houses.
• Enjoy free on-site parking, a rare treat in downtown Annapolis.
• Connect with friendly innkeepers who help plan your day with tailored tips, restaurant suggestions, and detailed visitor guides.

Address:

Flag House Inn, 26 Randall Street, Annapolis, MD 21401
Phone: 410-280-2721

Location:

Tilghman Island, MD

Highlights:

If you’re craving true peace and quiet, Black Walnut Point Inn is a hidden gem where stillness reigns. With sweeping water views and a bird sanctuary backdrop, it’s a dreamy escape for the soul.

We Recommend This For:

Couples, solo travelers, birdwatchers, and anyone looking to unplug in a tranquil waterfront setting.

What we Love:

Endless views of the Choptank River and Chesapeake Bay, six acres of serene gardens, and 52 acres of surrounding bird sanctuary.

• Stay at a peaceful waterfront inn surrounded by manicured lawns, gardens, and an expansive bird sanctuary.
• Relax in a hammock or chaise lounge with a good book and the sound of waves as your soundtrack.
• Unwind by the pool, play croquet, fish off the dock, or enjoy a gentle breeze while flying a kite on the great lawn.
• Soak In the beauty of uninterrupted views and the slow rhythm of life on the bay’s edge.

Address:

Black Walnut Point Inn, 4417 Black Walnut Point Road, PO Box 308, Tilghman Island, MD 21671
Phone: 410-886-2452

Romantic Getaways in Maryland:

Location:

Taneytown, MD

Highlights:

If you're in the mood for timeless elegance and historic charm, Antrim 1844 Country House Hotel is your Maryland dream stay. Nestled in the foothills of the Catoctin Mountains, this 1844 estate wraps you in luxury, history, and Southern hospitality.

We Recommend This For:

Couples, history enthusiasts, fine dining lovers, and anyone seeking a refined, all-in-one getaway in the countryside.

What we Love:

Historic architecture, gourmet dining, wine cellar access, and endless ways to relax or play across a grand 450-acre estate.

• Stay in one of 40 unique rooms filled with antique charm and modern touches, each with access to the beautifully preserved grounds.
• Dine at the fine restaurant and enjoy selections from the extensive wine cellar in a setting that feels like a different era.
• Explore the estate’s hidden corners, 14-foot-ceiling drawing rooms, and stately columns that echo 19th-century elegance.
• Unwind with a swim, a game of tennis or croquet, or a peaceful walk through the historic grounds and gardens.

Address:

Antrim 1844 Country House Hotel, 30 Trevanion Road, Taneytown, MD 21787
Phone: 410-756-6812

Location:

Chesapeake City, MD

Highlights:

If waterfront relaxation is what you're after, Ship Watch Inn delivers it with panoramic views and front-row seats to passing vessels on the canal. It’s one of South Chesapeake City’s most scenic and peaceful escapes.

We Recommend This For:

Couples, boat watchers, waterfront enthusiasts, and anyone seeking a peaceful stay in a quaint canal town.

What we Love:

Private decks on every room, canal-front hot tub, and exclusive perks at a nearby waterfront restaurant and marina.

• Stay in rooms with panoramic water views, each featuring private outdoor deck access for soaking in the sun and scenery.
• Relax in the waterside outdoor hot tub or lounge in peace as ships glide by on the canal.
• Dine at the nearby Chesapeake Inn Restaurant and Marina, where guests enjoy VIP perks and great local fare.
• Unplug and enjoy a true waterfront retreat in one of the few bed and breakfasts in South Chesapeake City.

Address:

Ship Watch Inn, 401 1st Street, Chesapeake City, MD 21915
Phone: 410-885-5300

Location:

Solomons, MD

Highlights:

For a classic Chesapeake Bay escape with harbor views and historic charm, Solomons Victorian Inn is a peaceful waterside gem. Each room offers sweeping views, and the island’s rich maritime history is just steps away.

We Recommend This For:

Couples, history buffs, boaters, and anyone seeking a relaxing bed-and-breakfast getaway with bay breezes.

What we Love:

Harbor views from every room, a gourmet three-course breakfast on the porch, and proximity to iconic local museums and maritime culture.

• Stay in waterfront rooms filled with Victorian elegance and panoramic views of the Chesapeake Bay harbor.
• Wake Up to a three-course European-style breakfast on the inn’s scenic porch before a day of exploring or unwinding.
• Experience the maritime legacy of Solomons Island with visits to the Calvert Marine Museum, Drum Point Lighthouse, and J.C. Lore Oyster House.
• Explore the area by bike, boat, or a peaceful waterfront stroll in this charming island town known for yacht building and bay life.

Address:

Solomons Victorian Inn, 125 Charles Street, P.O. Box 759, Solomons, MD 20688
Phone: 410-326-4811