Oakland Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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

Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (69 reviews)
"The restaurant next door was no longer open. We did find a lovely Italian restaurant just a mile or two down the road. Many places within a few minutes drive."

Reviewed on 2025/7/16

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Baja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is NT$3,439 per night from Jul 22 to Jul 23
NT$3,439
NT$3,920 total
Jul 22 - Jul 23
includes taxes & fees
9.6/10 Exceptional! (385 reviews)
"easy access to different amenities"

Reviewed on 2025/7/11

The Garrett Inn
See all 894 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 vacation 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 vacation 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 vacation packages and you could score some great off-season deals.
How many days is enough for Oakland?
With a well-organized 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 vacation 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 customize 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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation 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 vacation package to Oakland?
If you've got your Oakland vacation 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, favorite 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 vacation 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.