Luxury Vacation Rentals in Maryland
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 7 vacation rentals – enter your dates for availability.
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Springs
Next avail.
Dec 14 - Dec 16
14
Sweet deal
Augusta, West Virginia
Wander Augusta Valley
Next avail.
Dec 7 - Dec 9
12
5
Sweet deal
Oakland, Maryland
Wander Fern Hollow
Next avail.
Dec 2 - Dec 4
411
4.6
Elkton, Maryland
Wander Chesapeake Point
720
Nellysford, Virginia
Wander Blue Ridge Valley
Next avail.
Dec 2 - Dec 3
1016
5
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Mountains
Next avail.
Dec 2 - Dec 4
14
Washington, District of Columbia
Wander Washington D.C.
Next avail.
Feb 16 - Feb 18
48
4.8
Welcome to 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.
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Springs
Next avail.
Dec 14 - Dec 16
14
Sweet deal
Augusta, West Virginia
Wander Augusta Valley
Next avail.
Dec 7 - Dec 9
12
5
Elkton, Maryland
Wander Chesapeake Point
720
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Mountains
Next avail.
Dec 2 - Dec 4
14
Washington, District of Columbia
Wander Washington D.C.
Next avail.
Feb 16 - Feb 18
48
4.8
Sweet deal
Oakland, Maryland
Wander Fern Hollow
Next avail.
Dec 2 - Dec 4
411
4.6
Nellysford, Virginia
Wander Blue Ridge Valley
Next avail.
Dec 2 - Dec 3
1016
5
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Springs
Next avail.
Dec 26 - Dec 28
14
Elkton, Maryland
Wander Chesapeake Point
Next avail.
Dec 5 - Dec 8
720
Nellysford, Virginia
Wander Blue Ridge Valley
Next avail.
Dec 5 - Dec 7
1016
5
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Mountains
Next avail.
Dec 26 - Dec 28
14
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Maryland
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Springs
Next avail.
Dec 14 - Dec 16
14
Sweet deal
Augusta, West Virginia
Wander Augusta Valley
Next avail.
Dec 7 - Dec 9
12
5
Sweet deal
Oakland, Maryland
Wander Fern Hollow
Next avail.
Dec 2 - Dec 4
411
4.6
Elkton, Maryland
Wander Chesapeake Point
720
Nellysford, Virginia
Wander Blue Ridge Valley
Next avail.
Dec 2 - Dec 3
1016
5
Sweet deal
Shenandoah, Virginia
Wander Blue Ridge Mountains
Next avail.
Dec 2 - Dec 4
14
Washington, District of Columbia
Wander Washington D.C.
Next avail.
Feb 16 - Feb 18
48
4.8
Discover more of Maryland
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.