Weekend Getaways in Maryland for Couples

Want a relaxing couple’s escape without going too far? I’ve found that some of the best weekend getaways in Maryland for couples are just a short drive away—but they feel like a whole different world. Whether you're craving waterfront charm, mountain air, or a cozy inn to cuddle up in, you’ll find the perfect place to slow down and reconnect.

Highlights:

• Romantic stays in historic Annapolis: I’ve wandered these brick-lined streets hand-in-hand and watched sailboats drift by—it’s as charming as it gets.
• Seaside charm in St. Michaels: You’ll love the quiet vibe, fresh oysters, and sunset views over the harbor. I always recommend this one for a peaceful escape.
• Winery tours along the Chesapeake Wine Trail: I’ve sipped my way through a few of these vineyards—you’ll enjoy the relaxed pace and scenic countryside. Perfect for a low-key weekend with good wine and even better company.
• Cozy mountain cabins in Deep Creek Lake: When you need crisp air and a fireplace, this is the place. I’ve stayed in cabins here that feel like your own little hideaway in the woods.
• Scenic strolls and seafood dining on the Eastern Shore: There’s nothing like walking by the water and ending the day with crabcakes and wine. It’s classic Maryland, and you’ll fall in love with it like I did.

Best Weekend Getaways in Maryland for Couples: