Armando Iachini: Romantic Luxury Getaways Perfect for a Couples Retreat

Whisk away your sweetheart for a romantic getaway this Valentine’s Day. Explore luxurious accommodations, beautiful scenery, award winning food and dining, and the opportunity to relax and connect with your partner.

The following list of romantic retreats in Maryland all came very highly recommended from our readers (including the editor of this article: she celebrated both her engagement and her wedding “First Sight” on the pier at the lovely Swanendele Inn). So cozy up with your sweetheart and get ready for some romance!

Inn at Perry Cabin, St Michaels, is a premier resort and one of the most desirable and unforgettable places to spend time on Maryland’s Eastern Shore. Adding to the authentic charm of the resort is a zero-edge swimming pool, impeccably manicured gardens, and complementary bicycles, kayaks and paddleboards, to explore the historic town of St. Michaels via land or by water.

Unwind on Maryland’s Eastern Shore at the Chesapeake Bay Resort Hotel. Reconnect with family, friends, and colleagues at our 342-acre waterfront resort near Chesapeake Bay. Our AAA Four Diamond facilities include an 18-hole golf course, 150-slip marina, full-service spa, and countless ways to play in the sun. Explore Cambridge, Maryland, for both a rich history and a contemporary vibe.

Swanendele Inn is an elegant, family-owned country inn nestled on the shore of the Chesapeake Bay and St. Jerome’s Creek. St. Mary’s County offers history, outdoor recreation, and water, water everywhere! St. Mary’s has some of the earliest and finest colonial sites in the nation, War of 1812 and Civil War sites, and a rich maritime history illuminated by four picturesque lighthouses.

Waterfront historic home on the National Historic Register with our own executive chef Patrick Mahoney who prepares a delicious signature homemade two-course gourmet breakfast each morning of your stay!

This waterfront Bed & Breakfast is on the National Historic Register, has a private parking area, and is located in the heart of the quaint, historic town of Saint Michaels, across from Honeymoon Bridge, Chesapeake Bay Maritime Museum, Patriot Boat, and Hooper Straight Lighthouse.

Susannah’s Watch is a historic manor house on the Dixon Family Farm that has been transformed into a unique Bed & Breakfast on the banks of the Patuxent River.

Set on Kent Island, The Inn at Chesapeake Bay Beach Club welcomes guests with 77 beautifully-appointed guest rooms, suites and cottages, wellness-focused treatments at the full service spa and salon, and meeting space. Guests and locals alike enjoy multiple dining options with locally sourced and seasonal cuisine.

Savage River Lodge is completely surrounded by more than 700 acres of State Forest lands. We offer a rare brand of privacy, unparalleled relaxation and a myriad of opportunities for fun. For romantic weekends, family getaways (some cabins are even pet friendly), corporate retreats, reunions or just for random acts of escape, Savage River Lodge is an unforgettable experience!

Located where the Chesapeake Bay and Potomac River converge, Pier450 is a beach-chic hospitality destination on Maryland’s Western Shore. World-class restaurant, uniquely curated motel and an eclectic boutique on the waterfront with stunning sunset views.

Come and relax at one of our nine scenic rentals where you can soak in the salty waters, sunbathe in the undisturbed sand, and let nature soothe you with melodies of bird songs and the lapping ocean waves. The Scotland Yards rental properties give access to secluded beaches, to ensure the relaxation you deserve.

The Log Canoe Inn looks directly out at a waterfront view of the St. Michaels Harbor, and is nestled right in the heart of town, in the St. Michaels Historic District. Our property includes two historic buildings. Many renovations have been performed over the years to give our property new life and luxury amenities, but we strive to still keep the same history and charm that the home held hundreds of years ago.

Built as River View House in 1710 and an Inn since 1800, this is the oldest full-service Inn in America. Four of our 310 year old rooms were indeed slept in by Founding Father Robert Morris, George Washington and many other dignitaries of the day and since. This is a truly historic Inn, cozy with a natural patina running through. Friendly, great cuisine and understated professional service.

Rocky Gap Casino Resort is located in Rocky Gap State Park near Cumberland in the heart of Allegany County. Rocky Gap offers a casino, hotel, conference center, Bonkerz Comedy Club, two restaurants and a deli, indoor and outdoor event spaces, the only Jack Nicklaus Signature Golf Course in Maryland, a spa, indoor pool, fitness center, pro shop, self parking, and several outdoor recreational activities.

Nestled at the foot of the breathtaking Catoctin Mountains in Central Maryland, this beautiful 24-acre estate is renowned for its superb cuisine and upscale accommodations. Located just 15 minutes from Gettysburg, Antrim 1844 is the perfect location for romantic getaways, exquisite fine dining, elegant weddings, family reunions, corporate meetings, retreats, and much more.

Osprey Point Inn, Marina & Restaurant offers colonial-style elegance with luxurious resort grounds and amenities. At Osprey Point Inn, Restaurant and Marina, you’ll experience the perfect fusion of luxurious accommodations, elegant dining, and a relaxed and friendly environment. Located on the shores of Swan Creek in Rock Hall, Maryland, the Inn has easy access to the Chesapeake Bay.

Lake Pointe Inn offers all the comforts of a fine bed and breakfast with award-winning appointments in the arts and crafts tradition. This luxurious Deep Creek Lake Hotel is perched on the water’s edge of Deep Creek Lake’s pristine 65-mile shoreline, and offers plenty of space for adventurous and romantic couples to relax, unwind, and enjoy their getaways.

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