Find 5 Star 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 5 Star Hotels

This weekend
5 Jun - 7 Jun
Next weekend
12 Jun - 14 Jun

Our top choices for Oakland 5-star hotels

Exterior

Preston on the Lake 5 Bedroom House

Preston on the Lake 5 Bedroom House
5.0 star property
Oakland
Preston on the Lake 5 Bedroom House
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland.
Loft of Luxury by Taylor Made Deep Creek

Loft of Luxury by Taylor Made Deep Creek

Oakland MD
Get rates
Still don't see what you're looking for?
See all properties in Oakland.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

See all hotels in Oakland
Photo by Jenn Charbonneau
Open Photo by Jenn Charbonneau

Top Oakland Hotel Reviews

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.

Explore a world of travel with Expedia