Find Family Hotels in Oakland, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oakland Family Hotels

Next weekend
Jun 12 - Jun 14
In two weeks
Jun 19 - Jun 21

Our top choices for Oakland family-friendly hotels

Exterior

SureStay Plus Hotel by Best Western Keyser

SureStay Plus Hotel by Best Western Keyser
2.5 star property
Keyser
8.8 out of 10, Excellent, (563 reviews)
The price is ₩171,015
₩191,551 total
includes taxes & fees
Jun 15 - Jun 16
SureStay Plus Hotel by Best Western Keyser
Children's activities

Cannon Hill Inn

Cannon Hill Inn
2.0 star property
Rowlesburg
9.2 out of 10, Wonderful, (42 reviews)
The price is ₩117,238
₩182,837 total
includes taxes & fees
Jun 11 - Jun 12
Cannon Hill Inn
Children's area

The Lodge at Wisp Resort

The Lodge at Wisp Resort
2.0 star property
McHenry
7.2 out of 10, Good, (9 reviews)
The price is ₩314,511
₩456,193 total
includes taxes & fees
Jun 8 - Jun 9
The Lodge at Wisp Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at family-friendly hotels in Oakland

Breakfast included
Pool

Top Oakland Hotel Reviews

The Garrett Inn

The Garrett Inn

10/10 Excellent
"This is a charming, clean and affordable option to stay near Deep Creek Lake."
Tessa 2-night trip
Posted 8 days ago
The Garrett Inn

Frequently asked questions

What's Oakland like for family-friendly vacations?
The destination of Oakland is a great choice if you've been thinking about a vacation with your kids. The horseback riding, sledding, and camping sites are just a few things that make this an attractive vacation spot for families. Take to the air and fly into Morgantown, WV (MGW-Morgantown Municipal), which is located 31.8 mi (51.2 km) from the city center.
When's the best time to book a family-friendly vacation in Oakland?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Oakland are January, December, February, and May, with each month seeing an average of 31 inches of snowfall.
What's there to see and do with your family in Oakland?
Ruth Enlow Library of Garrett County, Adventure Sports Center International, and Wisp Resort are interesting attractions you and your family will enjoy exploring while you are staying in Oakland. Make sure you have lots of time for activities like Funland and Deep Creek Lake.