Oakland Holidays
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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
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
The price is AU$151 per night from 14 Dec to 15 Dec
AU$151
14 Dec - 15 Dec
includes taxes & fees
9.6/10 Exceptional! (408 reviews)
Everything about the place was perfect, centrally located, clean and comfortable. The farmhouse kitcsh was a little overboard but the place was very nice and very clean!
Reviewed on 29 Nov 2025
Amazing Central Location! Lakefront! Hot tub/dock!
Oakland MD
9.6/10 Exceptional! (45 reviews)
We had an excellent experience at Unwined. The host was welcoming and was very good at communicating with us. We were given useful information about the house and the area. When I asked a question via text once, I received a very quick response.
Reviewed on 3 Nov 2025
Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing
Oakland MD
9.8/10 Exceptional! (86 reviews)
A beautiful home and an awesome location! The owner was incredible to work with and so accommodating. I can’t say enough wonderful things about them! The home feels like a cabin and still has wonderful amenities like the hot tub that everyone enjoyed very much! Would definitely return.:-)
Reviewed on 1 Dec 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
