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Find 5 Star Hotels in Oakland, MD

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Check availability on Oakland 5 Star Hotels

Tonight
5 Apr - 6 Apr
Tomorrow
6 Apr - 7 Apr
Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr

Compare Oakland 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Preston on the Lake 5 Bedroom House
Exterior

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 Highway, 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

Get away to upscale Oakland! Enjoy the lake views, skiing, and camping.

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Swallow Falls
Photo by KM Moore
Open Photo by KM Moore

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Oakland?
You can find several pricing options for a 5-star hotel in Oakland on Expedia. How much you’ll pay will depend on when you travel, trip length and other factors. Compare all of the available accommodations for your preferred dates and make use of our pricing and other filters to land the ideal upscale stay.

  • Search for the lowest price per night

What makes a hotel 5 stars in Oakland?
In Oakland, a hotel must offer a certain level of upscale conveniences to be rated 5 stars. These may include gourmet restaurants, saunas and spas, on-site gyms, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their guest-focused service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may even offer special touches such as a welcome gift.
Are there any 5-star all-inclusive resorts in Oakland?
Find a luxurious retreat that includes your lodging, food, activities and entertainment in Oakland with our handy filter tool. Search for hotels with a 5-star rating and click on the “All inclusive” filter. Have a look at what’s included in the purchase price. That way, you can take full advantage of all the premium perks as soon as you arrive.
Are there any 5-star vacation rentals in Oakland?
Our site doesn’t offer any 5-star vacation rentals in Oakland. However, you can still find a range of top-rated retreats where the only item on your itinerary will be to unpack and have fun. See what’s available by checking out our vacation rentals in Oakland.