From the misty mountains of Western Maryland to the peaceful waterways of the Eastern Shore, Maryland offers a delightful mix of nature, history, and luxury. Whether you're staying near scenic Oakland in Garrett County or exploring the riverfront charm of Elkton in Cecil County, Wander’s properties bring you comfort, style, and access to a range of experiences. Enjoy cozy fireplaces in the woods, sleek kitchens for chef‑inspired meals, and outdoor decks perfect for quiet mornings or sunset views.
Luxury Vacation Rentals in Maryland
Book a Wander with inspiring views, hotel-grade amenities, modern workstations, top-tier cleaning, and 24/7 concierge service. It’s a vacation home, but better.
Top-Rated Luxury Vacation Rentals in Maryland
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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.
A Guide to Luxury Travel in Maryland
Luxury travel in Maryland is all about embracing contrast – rustic landscapes and refined design, Appalachian trails and colonial towns, lakeside retreat and riverside serenity. Our Wander homes reflect that blend: high‑speed WiFi for remote work, ergonomic workstations for productivity, and plush furnishings for those moments of stillness.
Whether you’re planning a family reunion, a remote workcation, or a mix of both, Maryland’s varied terrain and elegant stays deliver.
Maryland Weather: When Should You Visit?
Maryland is a year-round destination, with each season offering something special:
Spring (March–May): Wildflowers bloom, trails reopen, and fresh air makes it the perfect time for outdoor adventures without the crowds.
Summer (June–August): Warm days invite hiking, kayaking, and al fresco dining on the deck. Ideal for families and sun seekers.
Fall (September–November): Crisp air, colorful foliage, and cozy firelit evenings define Maryland’s most picturesque season.
Winter (December–February): Peaceful and quiet, with the chance of snow and all the coziness that comes with it—think hot drinks, reading nooks, and cabin vibes.
Food and Drink in Maryland
Maryland’s culinary culture is rich, rustic, and unmistakably local. Famous for its blue crab and Old Bay seasoning, the state also offers everything from Chesapeake oysters and rockfish to seasonal produce, cider donuts, and artisan cheeses.
Whether you’re exploring local farm stands, picking up seafood for a home-cooked feast, or visiting nearby breweries and wineries, you’ll find plenty to savor. Each Wander home is equipped with a modern kitchen and dining space, perfect for enjoying slow meals and memorable moments.
Points of Interest in Maryland
Wherever you stay, you’re never far from something worth exploring:
- Peaceful lakes, hiking trails, and outdoor recreation
- Historic downtowns with boutique shops and cafés
- Vineyards and breweries offering tastings and events
- Scenic drives through forests, farmland, and rolling hills
- Family-friendly attractions and cultural landmarks
Incredible Activities in and Around Maryland
Looking to do more than unwind? Maryland is made for outdoor adventure and quiet discovery:
- Boating, fishing, and paddleboarding on serene waterways
- Hiking, biking, and leaf-peeping along forested trails
- Visiting small-town festivals, antique markets, and museums
- Stargazing, fireside chats, and self-guided wine or cider tours
- Seasonal activities from snowshoeing to summer kayaking
FAQs
What Amenities Can I Expect in Wander's Maine Vacation Rentals?
All homes offer high-speed internet, luxury linens, smart home features, fully equipped kitchens, spa-style bathrooms, and modern workstations. Some also include hot tubs, forest views, or private access to trails or waterfronts.
What Amenities Can I Expect in Wander's Maryland Vacation Rentals?
All Wander homes include high-speed internet, fully equipped kitchens, spa-style bathrooms, luxury bedding, smart tech, and stylish interiors. Many properties also feature fireplaces, decks, hot tubs, or outdoor lounging spaces.
Where Else Does Wander Have Luxury Vacation Rentals?
Beyond Maryland, Wander offers exclusive vacation homes across the U.S., Canada, and Mexico, including:
- Hudson Valley, New York
- Lake Tahoe, California
- Telluride, Colorado
- Ponte Vedra Beach, Florida
- Bandon, Oregon
- Yucatán, Mexico
Wherever you stay, Wander ensures elevated design, premium service, and spaces that feel like home, only better.








