Oakland Vacation Packages

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Your Oakland Vacation

When a fun city break is calling, answer it with a vacation package to Oakland. The neighborhood of Blakeslee, which is great for nature, watersports and views, makes a wonderful base for your adventures. If going to see the sights is a priority during your trip to Oakland, be sure to swing by popular attractions like Swallow Falls State Park and Herrington Manor State Park. No matter your travel plans or the size of your budget, putting together a tailored Oakland vacation is a cinch with Expedia.

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
A waterfall cascading over rocks into a clear pool.

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.

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Ready to book your vacation to Oakland?

 

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Oakland Hotel Deals

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy Oakland MD
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Nov 24 to Nov 25
CA $154
CA $176 total
Nov 24 - Nov 25
includes taxes & fees
Baja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway Oakland MD
The price is CA $152 per night from Nov 17 to Nov 18
CA $152
CA $174 total
Nov 17 - Nov 18
includes taxes & fees
The Garrett Inn
Cove Creek Lodge

Cove Creek Lodge

2 out of 5
19638 Garrett Hwy Oakland MD
The price is CA $251 per night from Nov 18 to Nov 19
CA $251
CA $286 total
Nov 18 - Nov 19
includes taxes & fees
Cove Creek Lodge
See all 763 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

Stay near popular Oakland attractions

A waterfall cascading over a rocky cliff surrounded by lush greenery.

Swallow Falls State Park

9.8/10 (138 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.
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Frequently asked questions

How much does an Oakland vacation package cost?
You can grab a vacation package to this top destination on Expedia. But how much your vacation to Oakland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Oakland?
March, April and November are great times to look for cheap Oakland vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Oakland?
With a well-planned itinerary, you can easily hit the main Oakland sights in a handful of days. But if you want to discover hidden gems or go on day tours, consider booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Bagging a cheap Oakland package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Oakland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays individually. Better still, you can tailor your Oakland escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland?
If you're planning a spontaneous Oakland vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Oakland?

  1. Choose your dates: What you'd like to do in Oakland and your preferred season will help you decide when to travel.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and experiences. Your accommodations will probably be the largest expense during your trip to Oakland.
  3. Decide how long to go for: Now that you're more familiar with Oakland, you can work out the perfect length of your vacation. Put together a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the right Oakland vacation package for you.

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