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Compare and book 5 Star hotels in Oakland, Maryland

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Check availability on Oakland 5 Star Hotels

Tonight
5 Jul - 6 Jul
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6 Jul - 7 Jul
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11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Top Oakland 5 Star Hotels

Preston on the Lake 5 Bedroom House
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Preston on the Lake 5 Bedroom House

5.0 star property
Preston on the Lake 5 Bedroom House
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland.
Bear Hollow Lodge

Bear Hollow Lodge

20590 GARRETT HWY, Oakland, MD
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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.

Learn more about Oakland

Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic city centre where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

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Photo by KM Moore
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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Oakland?
You'll find various pricing options for a 5-star hotel in Oakland on Expedia. The amount you pay will depend on when you plan to travel, length of stay and other factors. Compare all of the available properties for your desired dates and make use of our pricing and other filters to find the perfect high-end stay.

  • Search for the lowest price per night

What makes a hotel 5 stars in Oakland?
From gourmet restaurants and all-day gyms to swimming pools and dreamy bedding, the 5-star experience in Oakland is all about comfort and luxury. But it calls for more than just upscale perks to earn a 5-star rating. Stays also have to provide extraordinary guest-centric services like beauty treatments, on-site dry cleaning and laundry and concierge services.
Are there any 5-star all-inclusive resorts in Oakland?
Use our handy filters to find a luxurious escape in Oakland where most of what you need is included in the price. From there, narrow your results for properties that have a rating of 5 stars and are categorised as "All inclusive." The main thing on the to-do list at these stays? Pure enjoyment and indulgence.