Oakland Vacations

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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

Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Riverside Suites
Riverside Suites
2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is AED 468 per night from May 1 to May 2
AED 468
AED 534 total
includes taxes & fees
1 May - 2 May
9/10 Wonderful! (62 reviews)
"This is very neat and appears to be newly renovated. I was very happy with my stay."

Reviewed on 30 March 2025

Riverside Suites
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 AED 380 per night from Apr 20 to Apr 21
AED 380
AED 433 total
includes taxes & fees
20 Apr - 21 Apr
9.6/10 Exceptional! (369 reviews)
"Awesome"

Reviewed on 13 April 2025

The Garrett Inn
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
8.4/10 Very Good! (44 reviews)
Perfect location!!
"We had a great time, the location was great and the place was clean"

Reviewed on 4 March 2025

Get rates
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
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 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.

Discover the most popular places to visit in Oakland

Gorgeous fall day! Lots of people, but there was room to walk

Swallow Falls State Park

5/5(29 reviews)

You can take time to visit Swallow Falls State Park during your travels to Oakland. Stroll along the riverfront in this family-friendly area, or seek out the ski slopes.

Swallow Falls State Park