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:

Go fishing and savor waterfront views on a fun family weekend trip.

Rod 'N' Reel Resort

Rod 'N' Reel Resort - 1 hour 10 minutes from Baltimore

- Go fishing and savor waterfront views on a fun family weekend trip.

Relax by the bay and explore island charm on a romantic spring getaway.

Wylder Hotel

Wylder Hotel, Tilghman Island - 1 hour 50 min

- Relax by the bay and explore island charm on a romantic spring getaway.

Walk along the harbor and enjoy sailing sights on an easy couples trip.

Annapolis Waterfront Hotel

Annapolis Waterfront Hotel

- Walk along the harbor and enjoy sailing sights on an easy couples trip.

Savor spa treatments and admire marina views on an affordable summer escape.

The Harbour Inn

St. Michaels Harbour Inn, Marina and Spa - 1 hour 30 minutes from Baltimore

- Savor spa treatments and admire marina views on an affordable summer escape.

Visit colonial rooms and enjoy tea service on a quick, unusual trip.

The Reynolds Tavern

The Reynolds Tavern - 35 minutes

- Visit colonial rooms and enjoy tea service on a quick, unusual trip.

Swim, golf, and explore attractions on an exciting family vacation.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

- Swim, golf, and explore attractions on an exciting family vacation.

Go skiing and enjoy mountain fun on an affordable winter weekend trip.

Wisp Resort

Wisp Resort

- Go skiing and enjoy mountain fun on an affordable winter weekend trip.

Discover waterfront attractions and enjoy indoor gardens on a fun trip with kids.

Gaylord National Resort

Gaylord National Resort

- Discover waterfront attractions and enjoy indoor gardens on a fun trip with kids.

Admire elegant suites and relax in quiet luxury on a romantic retreat.

The Columbia Inn at Peralynna

The Columbia Inn at Peralynna

- Admire elegant suites and relax in quiet luxury on a romantic retreat.

Watch Chesapeake sunsets and stroll peaceful grounds on a relaxing retirement getaway.

Great Oak Manor

Great Oak Manor, Maryland

- Watch Chesapeake sunsets and stroll peaceful grounds on a relaxing retirement getaway.

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