Photo by KM Moore

Find Family Hotels in Oakland, MD

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Pick from 5 Oakland Family Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Oak Mar Motel
Front of property
Oak Mar Motel
2.0 star property
9.2 out of 10, Wonderful, (163)
"Very clean and nice room"
Oak Mar Motel
Three Bedroom Cabin, Hot Tub, Wooded Lot, Access to Lake, Family, Pet Friendly.
Red Run Cabin - Winter
Three Bedroom Cabin, Hot Tub, Wooded Lot, Access to Lake, Family, Pet Friendly.
9.4 out of 10, Exceptional, (100)
"This was the second time we stayed at this house. We had beautiful weather, but the house was a wonderful retreat when we needed to cool down and relax. It's a quiet neighborhood that is located perfectly to get to town quickly or enjoy state parks."
Three Bedroom Cabin, Hot Tub, Wooded Lot, Access to Lake, Family, Pet Friendly.
The Garrett Inn
Exterior
The Garrett Inn
2.5 star property
9.6 out of 10, Exceptional, (351)
"A very quaint place- loved it!"
The price is SAR 406
SAR 462 total
includes taxes & fees
17 Nov - 18 Nov
The Garrett Inn
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.
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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.
How many hotels that welcome families will I find in Oakland?
Expedia has 209 hotels in Oakland that are great for families.
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?
Swallow Falls State Park, Herrington Manor State Park, and Wolf Den Run State Park 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 Wisp Resort and Adventure Sports Center International.