Oakland Holidays

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Where to stay in Oakland

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

Find hotels in Mountainside

Top hotels in Oakland

The Garrett Inn
The Garrett Inn
2.5 out of 5
17848 Garrett Highway, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is €118 per night from 2 Feb to 3 Feb
€118
includes taxes & fees
2 Feb - 3 Feb
9.6/10 Exceptional! (358 reviews)
"Very convenient location"

Reviewed on 28 Jan 2025

The Garrett Inn
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Oakland
9.8/10 Exceptional! (36 reviews)
An amazing winter getaway!
"We thoroughly enjoyed our stay! Magnolia is a beautiful well furnished home. We were lucky enough to have gotten lots of snow during our stay. It was so beautiful!! I would suggest additional heating on/in the main level bedrooms. There was a dramatic difference in that part of the house. Lots of ..."

Reviewed on 21 Jan 2025

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Lakefront, dog friendly, dock slip, hot tub, and fire pit
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Oakland
8.6/10 Excellent! (39 reviews)
Family get together
"Everything was just as described. Very clean and in a great location! Owner was so easy to work with. I would definitely book again!"

Reviewed on 1 Dec 2024

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In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
See all 884 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.

Frequently asked questions

How much does an Oakland holiday package cost?
You’ll find cheap prices on Expedia for your Oakland getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Oakland costs.
What are the cheapest months to go to Oakland?
You’re likely to find lower rates and greater availability in March, April and November. Take a look at our cheap Oakland holiday packages and you could score some great off-season deals.
How many days is enough for Oakland?
With a well-organised itinerary, you can easily hit the most popular Oakland sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Oakland holiday for longer.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is a cinch with Expedia. Once you’ve entered your destination and preferred dates under our “Packages” tab, set your maximum budget, apply some filters and see what’s available. You can customise your search by “Popular locations,” “Property type,” “Guest rating” and more. Order the results by “Price: low to high” to view the most economical Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your Oakland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Oakland?
If you’ve got your Oakland holiday dates locked in, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Oakland?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Oakland.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Oakland.
  3. Set the duration of your trip: Start by making a list of all the attractions you’d like to get to in Oakland. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that’s left now is to choose an Oakland holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.