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Find 5 Star Hotels in Oakland, MD

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

A Beautiful View
Terrace/patio
A Beautiful View
5.0 star property
10.0 out of 10, Exceptional, 1 review
"Cute place with updated furnishings and appliances, right across the street from Deep Creek Lake boat rentals, jet skis, restaurants and Lakeside Creamery. 15 minute drive to Swallow Falls and quick drive to any other activity offered."
A Beautiful View
A Winter View
House, Multiple Beds, Hot Tub | Living area | 50-inch TV with digital channels, fireplace
A Winter View
5.0 star property
A Winter View
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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The Lakehouse
House, Multiple Beds, Fireplace | Private kitchen | Fridge, microwave, oven, stovetop
The Lakehouse
5.0 star property
The Lakehouse

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Oakland.
Strawberry Fields

Strawberry Fields

10 Roman Ridge Road, 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.

Ready for an incredible adventure? Add even more enjoyment on your next trip to Oakland by treating yourself to the best of the best when it comes to lodging. It's an ideal pairing. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Oakland so popular in the last year. There's no reason to delay a getaway to Oakland any longer. Besides, the hotels in this area receive outstanding marks for guest services, so you know you'll be well cared for during your getaway. Our 5-star hotels in Oakland are the perfect places to relax in during your next getaway. You deserve an outstanding getaway.

Get a Great Deal on 5-Star Hotels in Oakland

Don't be afraid to be pampered during your trip, along with pristine rooms. Excellent customer care, granite-tiled bathrooms, and rejuvenating spa offerings are waiting for you. You're sure to find exactly the accommodation you need. Not only that, the hotels in this area receive high marks for guest services, so you know you'll be looked after during your getaway. What creature comforts do you want in your lodging? A concierge to help you suggest the next attraction to visit? A Swedish massage to help your cares fall away? Fluffy down pillows, lip-smacking main courses, and even space for your family pet in some cases...these hotels are one-of-a-kind. Want to see for yourself? Plenty of visitors recommend this location.

You won't sleep and order room service the entire time, though. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Oakland are the perfect place to relax after a busy day.

Make Your Escape

The results are in, and Oakland 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Select one of Expedia's Oakland 5-star hotels today and decompress in complete comfort at your convenience.

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.