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Find Romantic Hotels in Oakland, MD

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Compare Oakland Romantic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

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, (101)
"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.
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

Searching for romantic hotels in Oakland?
Are you looking for a romantic getaway? Our guests also enjoy Oakland for its lakeside setting and riverfront. You might consider checking out some of the nearby sights and attractions such as Swallow Falls State Park, Deep Creek Lake, or Youghiogheny River. If you’d like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you’ll be able to see everything on your list.
How many romantic hotels are there in Oakland?
Expedia has 253 romantic Oakland hotels for you to get cozy in.
When is the best time of year for a romantic getaway to Oakland?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures 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 is there to do in Oakland?
There’s nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Oakland. Couples looking to see some of the area’s natural features will enjoy Oakland for its lakeside setting and riverfront. You might think about visiting Swallow Falls State Park, Deep Creek Lake, or Youghiogheny River.
What's the best way to get to Oakland and around town during my romantic getaway?
These transportation options in Oakland might help your romantic trip get off to a smooth start: If you’re looking to fly to Oakland, the closest major airport is Morgantown, WV (MGW-Morgantown Municipal), located 31.8 mi (51.2 km) from the city center. If you’d like to explore around the area, you may want a rental car for your journey.