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Your Oakland Holiday

When a city break is calling, answer it with a holiday package to Oakland. The neighbourhood of Blakeslee, which is great for nature, watersports and views, makes a great base for your adventures. If taking in the sights is a must during your trip to Oakland, be sure to swing by big-name attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or budget, organising a tailored Oakland holiday is a cinch with Expedia.

Our guide on where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

dramatic autumn landscape photo taken in Swallow Falls State Park in Western , Maryland.

Mountainside

Mountainside might not have many top sights, but Deep Creek Lake and Deep Creek Lake State Park are two attractions nearby that you can check out.

Oakland Holiday

Oakland Essential Information

Language	English
Currency	U.S dollars
Population	1,900
Max Temp Winter	2ºC
Max Temp Summer	27ºC
Top Sights	Herrington Manor State Park, Wolf Den Run State Park and Swallow Falls State Park

Our pick of the best Oakland Hotel Deals

The Garrett Inn

17848 Garrett Highway Oakland MD

Fully refundableReserve now, pay when you stay

AU$163

18 Mar - 19 Mar

includes taxes & fees

9.6/10 Exceptional! (421 reviews)

Convenient parking. Clean room. Air conditioning just right. Convenient to stores and restaurants. Have stayed here twice now and when in the area, would stay again.

Reviewed on 11 Mar 2026

Baja Motel

1501 Maryland Hwy Oakland MD

Fully refundableReserve now, pay when you stay

8.8/10 Excellent! (90 reviews)

The room was clean and the king bed was quite comfortable. The heater was a bit loud but very effective, and the heated air fan in the bath was a nice touch; plenty of hot water, too. The microwave oven was small but worked well, and the mini-fridge was bigger than many we've seen. The staff were ...

Reviewed on 2 Mar 2026

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Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland MD

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See all 814 properties in Oakland

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.