15 Best Romantic (Weekend) Getaways in Maryland
Imagine a weekend escape where historic charm meets coastal serenity, where rolling vineyards lead to vibrant waterfronts, and where every sunset paints a masterpiece just for you and your loved one. Welcome to Maryland, a state often called “America in Miniature” for its incredible diversity, offering an unparalleled array of romantic getaways perfect for rekindling sparks or simply unwinding together. From the tranquil shores of the Chesapeake Bay to the majestic Appalachian mountains, Maryland beckons with intimate inns, luxurious resorts, and charming towns that promise unforgettable moments.
Whether you dream of spa indulgence, gourmet dining, outdoor adventures, or simply quiet moments by the water, you will discover a perfect haven here. The best times to visit are during the spring and fall, when the weather is mild, the scenery is breathtaking, and the crowds are thinner, allowing for truly intimate experiences. Planning your trip for these shoulder seasons also often means better deals on accommodations and activities, making your romantic escape even more accessible.
💰 Travel Cost Overview
| Category | Budget | Mid-range | Luxury |
|---|---|---|---|
| Accommodation (per night) | $80 – $150 | $150 – $250 | $250 – $500+ |
| Food & Dining (per day) | $30 – $60 | $60 – $120 | $120 – $250+ |
| Transportation (per day) | $10 – $25 (local transport) | $50 – $80 (car rental + gas) | $80 – $150 (premium car rental + parking) |
| Activities & Attractions (average entry fees, tours) | $10 – $30 | $30 – $70 | $70 – $150+ |
| Total Daily Budget | Low: $130 – $275 | Medium: $290 – $520 | High: $500 – $1050+ |
| Weekly Budget Estimates | Low: $910 – $1925 | Medium: $2030 – $3640 | High: $3500 – $7350+ |
The Chesapeake Beach Resort and Spa
Nestled on the Western Shore of the Chesapeake Bay, the Chesapeake Beach Resort and Spa offers a quintessential romantic escape with breathtaking water views and a focus on relaxation. This resort is unique for its blend of casual elegance and comprehensive amenities, making it a perfect all-in-one destination for couples. You can expect to spend your days indulging in the full-service spa, which offers couples’ massages and rejuvenating treatments, or lounging by the outdoor pool overlooking the bay. For those seeking a bit more activity, charter fishing trips depart directly from their marina, and the nearby Chesapeake Beach Railway Trail provides a scenic path for a romantic stroll or bike ride.
Dining options range from casual fare to elegant waterfront dining, ensuring every meal is an experience. This resort is ideal for couples seeking a tranquil retreat with plenty of opportunities for pampering and enjoying the beauty of the Bay. Its family-friendly aspects are minimal, truly allowing for a focus on adult relaxation. The best times to visit are late spring through early fall to fully enjoy the outdoor amenities and water activities.
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Gramercy Mansion
Step into a fairytale at Gramercy Mansion, a stunning Tudor mansion turned bed and breakfast nestled on 45 acres of manicured gardens in Stevenson, just outside Baltimore. What makes Gramercy truly unique is its historic grandeur combined with the intimate, personalized service of a B&B. Each of its individually decorated rooms and suites offers a distinct charm, often featuring fireplaces, whirlpool tubs, and antique furnishings, providing a luxurious and private escape. You can spend your days wandering through the beautiful formal gardens, exploring the organic farm, or simply relaxing in one of the mansion’s elegant common areas.
The gourmet breakfasts, often served in a charming dining room or even delivered to your suite, are a highlight. This destination is perfect for couples seeking a romantic, serene, and elegant retreat with a touch of history. It’s an ideal spot for anniversaries, honeymoons, or a quiet escape from city life. Its secluded nature ensures a peaceful experience, making it less suitable for families with young children.
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Dunes Manor Hotel & Suites
For couples who love the classic beach vacation with a touch of nostalgia, Dunes Manor Hotel & Suites in Ocean City offers a charming and unique experience. This landmark hotel stands out with its Victorian-era architecture and a grand oceanfront veranda, providing a picturesque backdrop for your romantic getaway. You can expect to wake up to the sound of waves, enjoy breakfast on the veranda overlooking the Atlantic, and then step directly onto the iconic Ocean City boardwalk for a stroll hand-in-hand.
The hotel features an indoor pool, a tea room for afternoon delights, and comfortable rooms, many with ocean views. While Ocean City can be bustling, Dunes Manor offers a quieter, more refined ambiance compared to some of the larger, modern resorts. It’s ideal for couples who appreciate classic charm, beach access, and a relaxing pace, perhaps reminiscing about earlier beach trips. It’s also suitable for couples who enjoy the lively boardwalk atmosphere but want a peaceful haven to return to.
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Gaylord National Resort
The Gaylord National Resort at National Harbor redefines the romantic getaway with its colossal glass atrium enclosing a vibrant indoor city. This resort is truly unique for its sheer scale and the immersive environment it creates, complete with themed restaurants, shops, and even a flowing river, all under one roof. You and your partner can stroll through the climate-controlled atrium, enjoy diverse dining experiences from upscale steakhouses to casual cafes, or unwind at the luxurious Relâche Spa.
Beyond the atrium, the resort offers stunning views of the Potomac River, an outdoor pool, and easy access to the numerous attractions of National Harbor, including the Capital Wheel, MGM National Harbor casino, and waterfront dining. This destination is perfect for couples who enjoy a lively, resort-style atmosphere with endless entertainment options at their fingertips, without having to leave the property. It offers luxury and convenience, making it ideal for a vibrant, yet relaxing, escape.
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Chez Amis Bed & Breakfast
Tucked away on a quiet street in historic Annapolis, Chez Amis Bed & Breakfast offers an intimate and charming escape perfect for couples seeking a personalized experience. This beautifully restored historic home boasts elegant rooms, each with unique decor and modern amenities, blending comfort with classic Annapolis charm. What makes Chez Amis special is its attention to detail and the warm hospitality of its hosts, who often provide insider tips for exploring the city.
You can expect to start your day with a delightful gourmet breakfast, often featuring local ingredients, before stepping out to explore Annapolis’s vibrant streets. The B&B is just a short walk from the Naval Academy, the historic State House, and the bustling Ego Alley waterfront, making it ideal for couples who love to discover a city on foot. This B&B caters to those who appreciate history, walkable cities, and a more personal touch than a large hotel, making it a perfect romantic base for exploring Maryland’s capital.
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The Harbour Inn
The Harbour Inn in St. Michaels offers a quintessential Eastern Shore experience, perfect for couples seeking waterfront tranquility and small-town charm. This inn is unique for its prime location directly on the harbor, providing stunning views of boats and the tranquil Miles River. Its elegant rooms and suites, many with private balconies, create an intimate and serene atmosphere.
You can spend your days watching the boats drift by, taking a romantic stroll through the charming streets of St. Michaels, known for its boutique shops, art galleries, and historic architecture. The Inn often provides bicycles for guests to explore the area, and sailing excursions depart nearby. Dining at the Inn’s waterfront restaurant is a highlight, offering fresh seafood and beautiful sunset views. It’s an ideal escape for couples who appreciate maritime beauty, historic towns, and a slower pace of life, making it perfect for a peaceful and romantic weekend.
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The Columbia Inn at Peralynna
The Columbia Inn at Peralynna offers a truly unique and luxurious bed and breakfast experience in Columbia, distinguished by its individually themed suites, each designed to transport you to a different corner of the world. From a Parisian boudoir to an African safari, every detail is meticulously crafted, making each stay a new adventure. This inn is special for its commitment to privacy and personalized service, often providing amenities like private entrances, in-room jacuzzis, and fireplaces.
You can expect a gourmet breakfast served at your convenience, often in your suite, enhancing the feeling of a private retreat. While Columbia itself is a planned community, the Inn provides a secluded oasis within easy reach of local dining and entertainment. It’s perfect for couples seeking a distinctive, intimate, and luxurious escape, especially those who appreciate unique decor and a highly private setting for their romantic getaway. It’s less about public spaces and more about the private sanctuary of your suite.
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The Inn at 202 Dover
The Inn at 202 Dover in Easton is a beacon of elegance and sophistication on Maryland’s Eastern Shore, offering a refined romantic experience in a meticulously restored historic mansion. What sets this inn apart is its commitment to luxury and impeccable service, combined with stunning architectural details and antique furnishings. Each suite is sumptuously appointed, often featuring fireplaces, spa-like bathrooms, and private sitting areas, providing a lavish and private sanctuary. You can expect a gourmet breakfast each morning, prepared with fresh, local ingredients, and often served in an elegant dining room.
The Inn is also home to a renowned fine-dining restaurant, The Peacock Restaurant, making it a culinary destination in itself. It’s ideally situated for exploring Easton’s charming boutiques and art galleries, or for day trips to nearby St. Michaels or Oxford. This inn is perfect for couples who desire a truly upscale, sophisticated, and tranquil retreat with a focus on gourmet dining and historic luxury.
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Wisp Resort
For adventurous couples who love the mountains and outdoor activities, Wisp Resort in Deep Creek Lake offers a dynamic and thrilling romantic getaway. This resort is unique as Maryland’s only ski resort, transforming from a winter wonderland to a vibrant summer playground. In winter, you can hit the slopes together for skiing or snowboarding, or enjoy snow tubing and ice skating.
Come warmer months, the resort offers mountain biking, zip-lining, a mountain coaster, and access to Deep Creek Lake for boating, swimming, and fishing. The lodging options range from hotel rooms to condos and townhomes, providing flexibility for couples. You can expect stunning mountain views and an array of activities that will keep you engaged and create memorable shared experiences. Wisp Resort is perfect for active couples who seek adventure and natural beauty, offering a blend of adrenaline-pumping activities and serene mountain relaxation.
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Princess Royale Resort
The Princess Royale Resort in Ocean City stands out as a grand oceanfront destination, offering a luxurious and spacious retreat for couples. While popular with families, its sheer size and amenities also provide ample opportunities for romantic relaxation. What makes it unique is its stunning 10,000-square-foot tropical atrium featuring an Olympic-sized indoor pool, lush foliage, and a café, creating a unique micro-climate perfect for year-round enjoyment.
You can expect direct access to the beach, multiple dining options including fine dining, a full-service spa, and various recreational activities. Many rooms and suites offer ocean views, allowing you to wake up to the sunrise over the Atlantic. This resort is ideal for couples who desire a comprehensive resort experience with direct beach access, excellent amenities, and the option for pampering at the spa. It allows for both lively fun and quiet moments together.
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Inn at the Black Olive
For the discerning couple seeking a truly luxurious and unique urban escape, the Inn at the Black Olive in Baltimore’s historic Fells Point offers an unparalleled experience. This boutique hotel is special for its exquisite Greek-inspired design, handcrafted furnishings, and a commitment to sustainable luxury. Each suite is a work of art, featuring amenities like deep soaking tubs, fireplaces, and private balconies with stunning city or harbor views.
You can expect a serene and sophisticated atmosphere, with exceptional personalized service. The Inn is renowned for its acclaimed Mediterranean restaurant, The Black Olive, which sources fresh, local ingredients, including seafood from its own boat. Its rooftop terrace provides breathtaking panoramic views of the city and harbor, perfect for a romantic evening. This inn is ideal for couples who appreciate fine dining, unique design, and a sophisticated urban setting, with the charm of Fells Point right outside their door.
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Great Oak Manor
Great Oak Manor, nestled on the tranquil shores of the Chesapeake Bay near Chestertown, offers a secluded and elegant romantic retreat. What makes this historic estate unique is its stunning waterfront location on 12 acres of manicured grounds, providing a sense of timeless grandeur and peaceful isolation. The manor house, dating back to the 18th century, has been meticulously restored, offering beautifully appointed rooms and suites, many with bay views and fireplaces.
You can expect to spend your days strolling through the gardens, relaxing by the outdoor pool, enjoying the private beach, or simply taking in the breathtaking sunsets over the Bay. Kayaks and bicycles are often available for guests to explore the natural surroundings. This manor is perfect for couples seeking a quiet, luxurious escape in a historic setting, where privacy and natural beauty are paramount. It’s an ideal spot for a truly unplugged and intimate experience.
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Tidewater Inn
The Tidewater Inn, located in the heart of historic Easton, Maryland, offers a charming and sophisticated urban retreat for couples. This boutique inn is unique for its blend of historic elegance and contemporary comfort, all within a beautifully restored building that exudes character. Each of its rooms and suites is individually designed with thoughtful touches, creating a cozy yet luxurious atmosphere.
You can expect personalized service and a peaceful base from which to explore Easton’s vibrant arts scene, upscale boutiques, and renowned restaurants, all within easy walking distance. The inn often features a lovely courtyard, perfect for a quiet morning coffee or an evening glass of wine. It’s an ideal choice for couples who appreciate historic charm, cultural exploration, and the convenience of being in the center of a lively small town. It offers an intimate alternative to larger resorts, focusing on personalized guest experience.
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Hyatt Regency Chesapeake Bay
The Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge offers a grand and comprehensive resort experience for couples seeking both relaxation and recreation. This sprawling resort is unique for its extensive array of amenities set against the backdrop of the Choptank River, a tributary of the Chesapeake Bay. You can expect to enjoy a championship golf course, a luxurious spa, multiple swimming pools (including an indoor heated pool with a waterslide), and a private beach area.
Water activities like kayaking and paddleboarding are readily available from their marina. Dining options are diverse, ranging from casual to fine dining, ensuring every palate is pleased. This resort is perfect for couples who desire a full-service, amenity-rich getaway with plenty of options for both activity and pampering, all within a beautiful natural setting. It’s large enough to offer privacy yet has enough to keep you entertained for days.
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Inn at Herrington Harbour
The Inn at Herrington Harbour in North Beach offers a serene and picturesque romantic escape, perfect for couples seeking a tranquil waterfront setting. This inn is unique for its location within a full-service marina, providing direct access to the beautiful Chesapeake Bay and a vibrant boating atmosphere. The rooms and suites are beautifully appointed, many offering private balconies with stunning views of the marina and the Bay.
You can expect to enjoy leisurely strolls along the docks, relax by the resort-style pool, or dine at the on-site waterfront restaurant, The Lighthouse Restaurant, known for its fresh seafood and panoramic views. For those who enjoy water activities, sailing and fishing charters are readily available. This inn is ideal for couples who appreciate maritime charm, peaceful surroundings, and beautiful sunsets, offering a quiet and intimate retreat away from the bustling crowds. It’s a true hidden gem for Bay lovers.
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Plan Your Visit
Maryland truly is a treasure trove of romantic possibilities, offering an incredible spectrum of weekend getaways that cater to every desire. From the grand luxury of waterfront resorts like the Hyatt Regency Chesapeake Bay to the intimate charm of historic B&Bs like Gramercy Mansion, and the adventurous spirit of Wisp Resort, you have a wealth of choices to craft your perfect escape. This guide has unveiled just 15 of these enchanting havens, each promising unique experiences, delicious dining, and moments that will deepen your connection.
So, whether you envision spa pampering, mountain thrills, or serene sunsets over the Bay, Maryland delivers. Start planning your romantic adventure today, keeping our practical cost overview in mind to tailor your trip to your budget. The Free State awaits, ready to inspire romance and create lasting memories for you and your beloved.
