Luxury Vacation Rentals for Families in Oakland

Luxury Vacation Rentals for Families in Oakland

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 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Oakland

Wander Fern Hollow property photo 1

Wander Fern Hollow

4 bedrooms•4.5 baths
Welcome to family adventures in Oakland

Welcome to family adventures in Oakland

Bring everyone together with Wander’s luxury family vacation rentals in Oakland, Maryland. Our hand-picked homes pair hotel-level consistency with the space families need, so grandparents, parents, and kids can settle in with ease.
Expect generous bedroom counts, kid-friendly sleeping options, airy living rooms for movie night, and chef-ready kitchens made for big breakfasts. Every stay includes ultra fast WiFi, smart-home controls, pristine cleaning, and 24/7 concierge support.
Enjoy private outdoor areas for playtime and flexible nooks inside for remote school or a quick call. With laundry, easy parking, and family essentials available on request, booking a Wander in Oakland means comfort handled and memories made.

Available soon in Oakland

Wander Fern Hollow property photo 1

Wander Fern Hollow

4 bedrooms•4.5 baths
2,085 US dollars for 3 nights•

~$185 less than other sites

All homes in Oakland

Wander Fern Hollow property photo 1

Wander Fern Hollow

4 bedrooms•4.5 baths
View all homes

Highlights in Oakland

Discover outdoor adventures, historic train museums, and scenic state parks perfect for an unforgettable family getaway in Oakland.
Swallow Falls State Park
Deep Creek Lake State Park
Herrington Manor State Park
Oakland B&O Railroad Museum
Wisp Resort

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 family vacation rentals in Oakland

Jacuzzi (1)
Hot tub (1)
Mountain view (1)
Fire pit (1)
Balcony (1)
Bbq area (1)
Fire place (1)
Day bed (1)
Dryer (1)
Washer (1)
Oven (1)
Ice maker (1)
Tv (1)
Wifi (1)
Ceiling fan (1)
Microwave (1)

More popular family destinations near Oakland

Family vacation rentals in Fort Washington
Family vacation rentals in Easton
Family vacation rentals in Elkton

Other popular amenities & vacation types in Oakland

Large group vacation rentals in Oakland
Pet-friendly vacation rentals in Oakland
Hot tub vacation rentals in Oakland
Discover more family fun in Oakland

Discover more family fun in Oakland

Tucked in Maryland’s Garrett County, Oakland delivers a four-season playground for families. Deep Creek Lake invites sunrise paddles and calm coves, while Swallow Falls State Park offers easy trails to roaring waterfalls. Winter brings ski runs, tubing, and the mountain coaster at Wisp Resort.
Between outdoor thrills, the town charms with its historic courthouse square and spirited community events, including the famed Autumn Glory celebration. Kids love the hands-on Discovery Center at Deep Creek Lake State Park, and quiet back roads make scenic drives effortless. This blend of nature, small-town warmth, and year-round adventure is why Wander’s luxury family vacation rentals in Oakland, Maryland are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Oakland

Why should I book a Wander in Oakland over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.
Every home in Oakland 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 family vacation rentals in Oakland?

Some of our most popular family vacation rentals in Oakland 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 family vacation rentals does Wander have available in Oakland?

Wander offers 1 family vacation rentals in Oakland, 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 family vacation rentals in Oakland?

You can check-in to Wander family vacation rentals in Oakland after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Oakland have WiFi access?

Yes. Every Wander home in Oakland 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.