15 Best Romantic (Weekend) Getaways in Maryland

Maryland may be a tiny state on the East Coast, but it’s jam-packed with diversity and beauty. When you visit this state, you can choose between the ocean, mountains, bays, cities, and countryside.

Whether you’re a die-hard Ravens fan toping everything off with Old Bay seasoning already, or you’re just passing through the Mid-Atlantic for a visit, you’re sure to fall in love with the charm of this place.

Here are our 15 picks for the best romantic weekend getaways in the state of Maryland:

1. The Chesapeake Beach Resort and Spa

The Chesapeake Beach Resort and Spa

Just an hour away from both Baltimore and Washington, D.C., the Chesapeake Beach Resort is perfect for city dwellers looking to escape into tranquility for a weekend.

Situated right on the water, this cozy resort brings you right to the Chesapeake Bay. For some, the ideal weekend could mean simply relaxing with the gorgeous views, indulging in some famous Maryland Crab Cakes. For others, a trip to the Chesapeake could mean charter fishing, kayaking, paddleboarding, jet skiing, and more.

Whichever type of guest you’re in the mood to be, the Chesapeake Beach Resort is ready to welcome and pamper you.

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

2. Gramercy Mansion

Gramercy Mansion

Smack dab in the middle of Baltimore’s historic district, the Gramercy Mansion waits to host you and your loved one. This romantic bed & breakfast is just minutes away from all the museums, art galleries, and fine dining that Baltimore has to offer. But for guests, it might feel like it’s worlds away.

The Gramercy resembles the epitome of unwinding and getting comfortable. Spend a lazy day at the B&B’s outdoor pool, swing on the old-fashioned rope swings, or get your adrenaline pumping with a game of tennis on-site.

And when you’re ready to snuggle in for the night with your loved one, relax by your own fireplace and whirlpool tub for two at the Gramercy.

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

3. Dunes Manor Hotel & Suites

Dunes Manor Hotel & Suites

Source: dunesmanor

Dunes Manor Hotel & Suites

Grab your sweetheart for a romantic getaway to the exciting beach town of Ocean City. At the Dunes Manor, you get direct ocean views and beachfront access. Not only that, but each room comes with a private balcony that looks directly out onto the Atlantic.

Soak up the sun all day long right in the backyard of the Dunes Manor. To take it up a notch, you can sunbathe on the hotel’s sundeck and order drinks right from your lounge chair! At night, you can dine at the Dunes’ oceanfront restaurant and wind down in the heated outdoor pool or Jacuzzi.

Website: http://dunesmanor.com/

4. Gaylord National Resort

Gaylord National Resort

Source: marriott

Gaylord National Resort

For DC natives or visitors of the DC area, the Gaylord National Resort creates an entirely unique lodging experience. The resort features a jaw-dropping 19-story glass atrium overlooking the National Harbor, amazing guests from the beginning.

Once you pick your jaw up from the floor, the views within the rest of the hotel are just as astounding. Each guest room displays top-of-the-line fixtures and touches, while the amenities are endless: indoor pool and whirlpool, first-class spa, state-of-the-art fitness center, several restaurants and shops, and of course, astounding views 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

Chez Amis Bed & Breakfast

Source: chezamis

Chez Amis Bed & Breakfast

When you think upscale, charming, personalized, and intimate, one thing comes to mind: Chez Amis Bed & Breakfast. This beautiful B&B with a name that translates to “Among Friends” in French encapsulates everything you hope for in a romantic weekend getaway.

Located in the heart of downtown Annapolis, Chez Amis prides itself as “a walker’s paradise” and welcomes you in like family. Start your morning with a three-course plated breakfast which alternates from sweet to savory. You may get anything from peach muffins to strawberry yogurt parfaits to baked eggs with six cheeses.

When you’re refueled enough for the day, you and your loved one can explore the cobblestoned streets and waterfront views of Maryland’s gorgeous capital city right outside your doorstep.

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

6. The Harbour Inn

The Harbour Inn

Source: harbourinn

The Harbour Inn

In picturesque St. Michaels along the Eastern Shore of the Chesapeake Bay, enjoy a truly romantic weekend with your significant other. The Harbour Inn provides luxurious accommodations year-round right on the water.

No matter where you stay at the Harbour, you’ll have your own private balcony overlooking the marina. Wake up to the sunrise over the docks next to your loved one.

The Inn also provides complimentary bikes for guests to tour the town like a local. Peddle past the Chesapeake Bay Maritime Museum, boutique shops, antique treasure coves, and restaurants from the Inn. Or if you want to get your hands dirty, you must try crabbing—a Maryland staple. Try to catch the delicious blue crabs yourself! If you succeed, the Inn’s chefs will even cook your catch for dinner.

Website: http://harbourinn.com/

7. The Columbia Inn at Peralynna

The Columbia Inn at Peralynna

Source: mycolumbiainn

The Columbia Inn at Peralynna

Nestled in quiet Howard County, the Columbia Inn provides a tranquil oasis for love birds. This mansion-turned-hotel is perfect for couples who want to tune the rest of the world out and refocus on what is important: each other.

Enjoy wine and cheese by the crackling fire, curl up with a book in the hotel’s lending library, or retreat to your personal guest room. And these are not any B&B lodgings; each suite resembles a five-star luxury suite, complete with fine linens and modern furnishings.

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

8. The Inn at 202 Dover

Inn at 202 Dover

Source: innat202dover

Inn at 202 Dover

Visit the Inn at 202 Dover, a proud member of the Historic Hotels of America and a AAA Four Diamond recipient, on your next romantic getaway in Maryland. This mansion built in 1874 now serves guests in optimal hospitality.

Choose between a variety of themes when you pick out your room at the Inn. You can stay in a Victorian suite, Africa Safari suite, Asia suite, and more. As you could imagine, the Safari suite invokes rich mahoganies and deep colors, while the Victorian suite utilizes refined furnishings and ornate décor. Relax by the personal fireplace or soak in the corner whirlpool tub in this room.

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

9. Wisp Resort

Wisp Resort Hotel

Source: wispresort

Wisp Resort Hotel

For mountain lovers, Maryland even has a place for you. Travel to the Western corner of the state to immerse yourself in the Appalachian Mountains.

At the Wisp Resort in Deep Creek, you and your special someone can enjoy a front-row ticket to skiing, snowboarding, golfing, and other activities. The winter months are of course the most popular times to visit this region. If you snag one of the deluxe rooms, you’ll even have the convenience of being able to ski-in and ski-out! Now that’s pretty cool.

When you’re exhausted from a day on the slopes, unwind in the resort’s indoor heated pool or with a tasty cup of hot chocolate.

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

10. Princess Royale Resort

Princess Royale Resort

Vacation seaside with your sweetheart at the Princess Royale in Ocean City. This resort is completely on the water, giving you full access to the white sandy beaches of the East Coast. And before you even get to the beach you can see it surrounding you in the resort’s four-story oceanfront glass atrium.

Daze away under the sun on the beaches or on the Princess Royale’s sundeck to avoid the crowds. Take advantage of the complimentary whirlpools, saunas, and indoor heated pool on-site. And in season, the resort even hosts live music and comedy shows for guests to enjoy.

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

11. Inn at the Black Olive

Inn at the Black Olive

When you’re in Baltimore, you have to live it up. And that’s exactly what the Black Olive is here to do. This modern hotel with sleek décor and eco-friendly accommodations makes you feel just as refined as you should.

This Inn exudes minimalist elegance. Adorned with vibrant colors, designer accents, and Zen-style bathrooms, it doesn’t get more chic than this. And the Black Olive boasts its status as Baltimore’s Premier Boutique Organic Hotel. We’re familiar with organic foods, but an organic hotel? What?

What this means is that everything from the building materials to the room service meals are made and grown organically. So you can help save the planet while you also save your sanity!

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

12. Great Oak Manor

Great Oak Manor

Source: greatoakmd

Great Oak Manor

When you combine the beauty of Maryland’s Eastern Shore with the magnificence of a completely renovated 18th-century estate, great things happen. Great things, or shall we say, Great Oaks.

Whisk your darling away to the Great Oak Manor for a peaceful weekend away from reality. This historic B&B pays homage to its 1700s roots with period décor and replica antiques, but offers comfort to guests with modern amenities and private lodgings.

During the day, take a kayak, canoe, or paddleboard out on the water, just steps away from the Manor’s doors. Relax at night by the waterside firepits with your loved one. And when you wake up in the morning, your belly won’t stay empty for long; indulge in farm fresh eggs, meats, fresh baked pastries, homemade blackberry jam, and more.

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

13. Tidewater Inn

Tidewater Inn

Source: tidewaterinn

Tidewater Inn

Established in 1712, this Inn is older than America itself. The Tidewater has set the gold standard for hotels in this waterfront region of Maryland for over 300 years.

Luxuriate in upscale bed linens and luscious temper-pedic mattresses when you stay at the Tidewater. You’ll feel like royalty of the bygone era when you walk into the building, but then regal guests of modern times once you reach your private room.

And if you happen to be in town in mid-November, make sure you catch the Annual Brew & Oyster Brawl. This festival hosts live music by local favorites, an open bar, and, of course, oysters galore. Try oysters on the half shell, fried oysters with dipping sauces, char-grilled oysters sautéed in either lemon parsley butter or BBQ and bacon, and more.

Website: http://tidewaterinn.com/

14. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Whether you like golf, the water, or luxury, this Hyatt on the Chesapeake Bay has it for you. Stop by this hotel for a weekend away with your loved one where you can find pure romance and bliss.

The massive golf course on-site would excite any golf enthusiast. And with views overlooking the majestic bay, you just can’t beat it.

If you’re not looking for golf, don’t worry! There’s a beach, marina, tennis court, yoga studio, and bustling town of Cambridge all within reach of the Hyatt Regency.

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

15. Inn at Herrington Harbour

Inn at Herrington Harbour

The Chesapeake Bay really doesn’t get old. For Marylanders, this is the crème de la crème.

This picture-perfect Inn couldn’t be in a better place: oceanfront with the marina directly behind. This way, when you and your sweetheart visit, you can lounge along the Inn’s private sandy coast or plunge into the harbor for boating and crabbing.

And when you don’t want to leave the hotel, cool down at their Olympic sized pool, play a game of volleyball or cornhole, savor a picnic, or dine at the restaurant on-site. At the Inn at Herrington Harbour, the fun never runs out.

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

Where to stay: Best Hotels in Maryland (MD)
Lowest Price Guarantee

List of Image Sources

15 Best Romantic (Weekend) Getaways in Maryland:

The Chesapeake Beach Resort and Spa