Luxury Vacation Rentals in Maryland

Set your sights on a better stay with Wander. Our luxury vacation rentals in Maryland pair the polish of a five-star hotel with the comfort of a private home, so downtime feels effortless and work time stays productive.

Choose from coastal sanctuaries, wooded hideaways, and modern retreats, each with chef-grade kitchens, crisp linens, ultra fast WiFi, and dedicated workstations. Many feature pools, hot tubs, and fitness spaces, all maintained to exacting standards with pristine cleaning and 24/7 concierge support. The photos always match the experience, and every space is set for easy living from first light to last.

In Maryland, shorelines, cities, and mountains sit within easy reach. The Chesapeake Bay shapes life on the water, from classic schooners in Annapolis to lighthouse-dotted inlets on the Eastern Shore. On the Atlantic side, wild dunes and roaming ponies define Assateague, with lively beaches a short drive away.

Head west to hemlock forests, the C&O Canal towpath, and Deep Creek Lake, with hiking, boating, and winter runs at Wisp. In between, Baltimore’s harbor, galleries, and theaters add urban energy, while small towns celebrate maritime heritage and blue crab traditions. This breadth is why Wander’s luxury vacation rentals in Maryland are the perfect choice, whether you’re traveling for work or leisure.