Luxury Vacation Rentals for Large Groups 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 1 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Maryland

Wander Fern Hollow

4 bedrooms•4.5 baths

4.3

Welcome to your large group retreat in Maryland

Bring everyone together with Wander's luxury vacation rentals for large groups in Maryland. From waterfront estates on the Chesapeake Bay to expansive lakefront retreats in the mountains, each home is designed for effortless gathering and privacy in equal measure.

Expect multiple ensuite bedrooms, generous great rooms, chef's kitchens with double appliances, indoor-outdoor dining, and parking for the whole crew. Every stay includes pristine cleaning, ultra fast WiFi, and 24/7 concierge service so you can focus on time together.

Whether it is a milestone celebration, an offsite, or a multi-family getaway, our luxury vacation rentals in Maryland make large-group travel easy and elevated. Book with confidence knowing every home looks like the photos and is expertly operated.

All homes in Maryland

Wander Fern Hollow

4 bedrooms•4.5 baths

4.3

View all homes

Highlights in Maryland

Discover diverse group adventures across Maryland, from exploring historic harbors and battlefields to enjoying scenic waterways and vibrant city life.

Inner Harbor

Annapolis City Dock

Ocean City Boardwalk

Antietam National Battlefield

Assateague Island National Seashore

Deep Creek Lake

Fort McHenry National Monument and Historic Shrine

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for large group vacation rentals in Maryland

Other popular amenities & vacation types in Maryland

Family vacation rentals in Maryland

Hot tub vacation rentals in Maryland

Lakefront vacation rentals in Maryland

Discover more large groups activities in Maryland

Maryland delivers variety without the long drives. Sunrise over the Chesapeake Bay, winding coves lined with sailboats, and heritage lighthouses set an elegant coastal mood. On the Atlantic side, broad beaches and quiet barrier islands offer room to roam.

Head west for rolling farmland, vineyard-dotted hills, and the forested peaks around Deep Creek Lake. Seasons matter here, with fiery foliage in fall, ski days at Wisp, and breezy summers on the water.

With culture-rich waterfront towns and scenic routes connecting it all, the state makes group itineraries simple and memorable. This is why Wander's luxury vacation rentals in Maryland are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Maryland

Why should I book a Wander in Maryland over other large group vacation rentals?

Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.

Every home in Maryland delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular large group vacation rentals in Maryland?

Some of our most popular large group vacation rentals in Maryland include Wander Fern Hollow and Wander Fern Hollow. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different large group vacation rentals does Wander have available in Maryland?

Wander offers 1 large group vacation rentals in Maryland, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s large group vacation rentals in Maryland?

You can check-in to Wander large group vacation rentals in Maryland after 4.00pm and check-out before 10.00am.

Do Wander’s large group vacation rentals in Maryland have WiFi access?

Yes. Every Wander home in Maryland has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.