Top 15 Romantic Weekend Getaways in Maryland

Maryland may occupy a modest area on the East Coast, yet it is rich in diversity and natural beauty. Visitors to this state can explore various attractions, including the ocean, mountains, bays, urban areas, and rural landscapes.

Whether you are a passionate Ravens supporter savoring everything with Old Bay seasoning or merely traversing the Mid-Atlantic region, you will likely be captivated by the unique charm of Maryland.

Below are fifteen curated selections of the most enchanting romantic weekend getaways in Maryland:

1. The Chesapeake Beach Resort and Spa

Located merely an hour from both Baltimore and Washington, D.C., the Chesapeake Beach Resort offers a splendid retreat for city residents seeking tranquility for the weekend.

Perched along the water’s edge, this inviting resort immerses you in the beauty of the Chesapeake Bay. For some, the perfect weekend may entail unwinding while enjoying stunning vistas and relishing delectable Maryland Crab Cakes. For others, a visit to the Chesapeake may involve charter fishing, kayaking, paddleboarding, jet skiing, and a plethora of other activities.

Regardless of how you choose to spend your time, the Chesapeake Beach Resort is prepared to accommodate and indulge you.

Website: http://www.chesapeakebeachresortspa.com/

2. Gramercy Mansion

Situated in the heart of Baltimore’s historic district, the Gramercy Mansion is ready to host you and your partner. This charming bed & breakfast is conveniently located just moments away from Baltimore’s museums, art galleries, and fine dining establishments. Yet, for guests, it feels like a peaceful retreat.

The Gramercy embodies comfort and relaxation. Spend your day lounging by the bed & breakfast’s outdoor pool, enjoy the nostalgic charm of traditional rope swings, or energize yourself with an exciting game of tennis.

When evening arrives, retreat for a cozy night in with your loved one, enjoying the warmth of your private fireplace and a whirlpool tub designed for two at the Gramercy.

Website: http://www.gramercymansion.com/

3. Dunes Manor Hotel & Suites

Take your beloved for a romantic escape to the vibrant beach community of Ocean City. At the Dunes Manor, guests are treated to direct ocean views and easy beachfront access. Each room is equipped with a private balcony overlooking the Atlantic Ocean.

Soak up the sun right in your own backyard at the Dunes Manor. For a heightened experience, relax on the hotel’s sundeck and enjoy refreshments delivered straight to your lounge chair! In the evening, savor a meal at the Dunes’ oceanfront restaurant before unwinding in the heated outdoor pool or Jacuzzi.

Website: http://dunesmanor.com/

4. Gaylord National Resort

For Washington D.C. residents or visitors, the Gaylord National Resort offers a distinctive lodging experience. The resort features an awe-inspiring 19-story glass atrium overlooking the National Harbor, captivating guests upon arrival.

The breathtaking views continue throughout the hotel, with each guest room showcasing high-quality fixtures and decor. The resort’s vast amenities include an indoor pool and whirlpool, a premier spa, a state-of-the-art fitness center, numerous dining venues, and unmatched vistas of our nation’s capital from the glass dome.

Website: http://www.marriott.com/hotels/travel/wasgn-gaylord-national-resort-and-convention-center/

5. Chez Amis Bed & Breakfast

When envisioning sophistication, charm, personalization, and intimacy, one establishment comes to mind: Chez Amis Bed & Breakfast. This elegant B&B, which translates to “Among Friends” in French, embodies the essence of a romantic weekend escape.

Located in the vibrant heart of downtown Annapolis, Chez Amis is celebrated as “a walker’s paradise” and welcomes guests with familial warmth. Begin your day with a meticulously prepared three-course breakfast that alternates between sweet and savory, ranging from peach muffins to strawberry yogurt parfaits and baked eggs with multiple cheeses.

Once rejuvenated for the day, you and your partner can stroll the charming cobblestoned streets and enjoy the scenic waterfront views of Maryland’s spectacular capital city just outside your door.

Website: http://www.chezamis.com/

6. The Harbour Inn

In the scenic St. Michaels on the Eastern Shore of the Chesapeake Bay, you can relish an authentically romantic weekend with your partner. The Harbour Inn offers year-round luxurious accommodations, ideally situated by the water.

Regardless of where you stay at the Harbour, a private balcony with views of the marina awaits. Start your day with your loved one, watching the sunrise over the docks.

The Inn also lends complimentary bicycles, allowing guests to explore the town like locals. Navigate past the Chesapeake Bay Maritime Museum, unique boutiques, antique shops, and delightful dining experiences. For those seeking a hands-on experience, Maryland is renowned for crabbing—try your luck at catching blue crabs, and the Inn’s chefs will prepare your fresh catch for dinner.

Website: http://harbourinn.com/

7. The Columbia Inn at Peralynna

Nestled in serene Howard County, the Columbia Inn serves as a peaceful haven for couples. This former mansion transformed into an inn offers the ideal setting for those wishing to disconnect from the outside world and focus on one another.

Relish wine and cheese by the crackling fireplace, curl up with a book in the hotel’s library, or retire to your private guest room. These accommodations transcend typical B&B lodgings; each suite resembles a luxurious five-star suite, complete with upscale linens and contemporary furnishings.

Website: http://www.mycolumbiainn.com/

8. The Inn at 202 Dover

Visiting the Inn at 202 Dover, a member of the Historic Hotels of America and AAA Four Diamond recipient, is a must on your next romantic endeavor in Maryland. Constructed in 1874, this mansion now provides its guests with exceptional hospitality.

Guests can choose from a variety of themes when selecting their accommodation. Options include a Victorian suite, Africa Safari suite, Asia suite, among others. The Safari suite features rich mahoganies and deep tones, while the Victorian suite boasts refined furnishings and exquisite decor. Relax in front of your personal fireplace or indulge in a corner whirlpool tub in your selected room.

Website: http://www.innat202dover.com/

9. Wisp Resort

For those who appreciate mountainous terrains, Maryland has options available. Journey to the western region of the state to immerse yourself in the beauty of the Appalachian Mountains.

At the Wisp Resort in Deep Creek, you and your significant other can revel in skiing, snowboarding, golfing, and additional activities. Winter undeniably draws the most visitors to this area. If you secure one of the deluxe rooms, you can enjoy the convenience of skiing directly in and out! That’s certainly a highlight.

After a day on the slopes, unwind in the resort’s indoor heated pool or treat yourself to a comforting cup of hot chocolate.

Website: http://www.wispresort.com/

10. Princess Royale Resort

Experience a beach vacation with your partner at the Princess Royale in Ocean City. This resort is situated directly by the water, providing easy access to the pristine sandy beaches of the East Coast. Before even reaching the beach, guests are greeted by the resort’s stunning four-story oceanfront glass atrium.

Unwind beneath the sun either on the beach or at the Princess Royale’s sundeck to escape the crowds. Enjoy complimentary whirlpools, saunas, and an indoor heated pool available for guests. Additionally, during peak seasons, the resort hosts live performances and comedy shows for entertainment.

Website: http://www.princessroyale.com/

11. Inn at the Black Olive

When visiting Baltimore, one should experience indulgence at its finest, and that is precisely what the Black Olive offers. This contemporary hotel, characterized by its sleek design and eco-friendly accommodations, elevates your stay to a refined level.

The Inn reflects minimalist sophistication, adorned with vivid colors, designer accents, and Zen-inspired bathrooms, exemplifying chic style. Moreover, the Black Olive prides itself as Baltimore’s premier boutique organic hotel, providing guests with an entirely unique experience.

This commitment to sustainability encompasses everything from the construction materials to the organic meals served via room service. Visitors can feel good about supporting eco-friendly practices while relishing their stay!

Website: http://www.innattheblackolive.com/

12. Great Oak Manor

The combination of Maryland’s Eastern Shore’s natural allure and a meticulously restored 18th-century estate creates a picturesque experience. Whisk your loved one away to Great Oak Manor for a serene retreat from everyday life.

This historic B&B honors its 1700s heritage with period decor and antique reproductions while providing modern comforts to its guests.

During daylight hours, embark on kayaking, canoeing, or paddleboarding adventures just steps from the Manor. In the evenings, enjoy the ambiance of fireside gatherings along the water. Furthermore, awaken each morning to a delightful brunch featuring farm-fresh eggs, meats, homemade pastries, and berry preserves.

Website: http://www.greatoakmd.com/

13. Tidewater Inn

Established in 1712, this Inn pre-dates America itself and has long served as the gold standard for accommodations within Maryland’s waterfront region for more than three centuries.

Indulge in upscale bedding and luxurious Temper-Pedic mattresses during your stay at the Tidewater. Experience the grandeur of a bygone era upon entering the building, but feel like a modern-day royal once in your private suite.

Should you find yourself in town during mid-November, do not miss the Annual Brew & Oyster Brawl. This lively festival features performances by local musicians, an open bar, and an array of oyster dishes, including half-shell oysters, fried oysters with dipping sauces, and oyster varieties grilled with flavorful seasoning.

Website: http://tidewaterinn.com/

14. Hyatt Regency Chesapeake Bay

This Hyatt, located on the Chesapeake Bay, offers golf, water activities, and luxurious amenities, catering to a variety of preferences. Invite your partner to enjoy romance and bliss during a weekend retreat.

The expansive on-site golf course is bound to enchant any golf enthusiast, coupled with breathtaking views of the serene bay, creating an ideal atmosphere.

For those not inclined toward golf, fear not! A beach, marina, tennis court, yoga studio, and the quaint town of Cambridge are all easily accessible from the Hyatt Regency.

Website: https://chesapeakebay.regency.hyatt.com/en/hotel/home.html

15. Inn at Herrington Harbour

The Chesapeake Bay consistently captivates visitors. For Maryland residents, it presents a quintessential escape.

This idyllic inn is splendidly situated oceanfront, with the marina located just behind it. Thus, couples can spend their time lounging on the Inn’s private sandy beach or venturing into the harbor for boating and crabbing activities.

Should you choose to remain on-site, take advantage of the Olympic-sized pool, participate in a volleyball or cornhole match, enjoy a picnic, or dine at the on-premises restaurant. At the Inn at Herrington Harbour, your enjoyment is limitless.

Website: http://www.herringtonharbour.com/beach-lodging/