Oakland Vacations from $452

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Your Oakland Vacation

Pick a Oakland vacation package and focus on what matters — having fun. There's no more stressful planning, just more free time to experience the charms of this awesome city, such as its rich history and friendly locals. When the time comes to venture out and explore, be sure to put Patriots Sports Plex and Borough House Plantation on the to-do list for your trip to Oakland. Whatever your travel plans or the size of your budget, putting together a tailored Oakland vacation is a breeze with Expedia.

The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn Columbia

Sleep Inn Columbia

2.5 out of 5
Price was $544, price is now $452 per person
$452
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Columbia (CAE)
8.2/10 Very Good! (1,001 reviews)
Room was too damp. Bathroom was too small

Reviewed on Aug 31, 2025

Courtyard by Marriott Columbia Downtown at USC

Courtyard by Marriott Columbia Downtown at USC

3 out of 5
Downtown Columbia
Price was $928, price is now $765 per person
$765
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Columbia (CAE)
8.8/10 Excellent! (1,000 reviews)
I really enjoyed my stay here. The hotel was very clean and the staff were all very polite and friendly. The food from the bistro downstairs was really great. There is a pool but no hot tub. The parking garage is a very tight squeeze, and there is no valet parking. The hotel is within walking distance of several different restaurants which is very convenient. The room was a little noisy though and there was a lot of street noise we could hear throughout the night. I would stay here again, especially if I had an event at USC.

Reviewed on Aug 28, 2025

Sleep Inn Airport

Sleep Inn Airport

2.5 out of 5
Price was $601, price is now $497 per person
$497
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Columbia (CAE)
7.8/10 Good! (793 reviews)
Everything was amazing

Reviewed on Sep 1, 2025

Homewood Suites by Hilton Columbia

Homewood Suites by Hilton Columbia

3 out of 5
Price was $696, price is now $582 per person
$582
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Columbia (CAE)
8.2/10 Very Good! (868 reviews)
Staff was very very pleasant and courteous. Enjoyed the stay, enjoyed the room, enjoyed it all. Indoor pool and hot tub were a plus. Well done.

Reviewed on Aug 31, 2025

Hampton Inn Columbia I-26/Harbison Blvd.

Hampton Inn Columbia I-26/Harbison Blvd.

2.5 out of 5
Price was $667, price is now $564 per person
$564
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Columbia (CAE)
9.2/10 Wonderful! (1,007 reviews)
The hotel was average. There are lots of restaurants and stores in close proximity.

Reviewed on Aug 31, 2025

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Discover the most popular places to visit in Oakland

The beautiful black waters of Swan Lake form the setting for the spectacular Iris Gardens. The lake is dotted with colorful islands, and wildlife is abundant. The only public park in the United States to feature all eight swan species, Swan Lake-Iris Gardens is also home to some of the nation's most intensive plantings of Japanese iris

Swan Lake Iris Gardens

Explore the great outdoors at Swan Lake Iris Gardens, a lovely green space in Sumter. While you're here, you can savor the top-notch restaurants.

Swan Lake Iris Gardens

Sumter Mall

You can search for that perfect souvenir at Sumter Mall during your visit to Sumter. While you're here, you can savor the top-notch restaurants.

Sumter Mall

Dillion Park

After visiting Dillion Park, make a plan to see the other sights and activities in Sumter. While you're here, you can savor the top-notch restaurants.

Dillion Park

Oakland Hotel Deals

Woodspring Suites Sumter Near Shaw Afb

Woodspring Suites Sumter Near Shaw Afb

2.5 out of 5
2715 Broad Street, Sumter, SC
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Sep 5 to Sep 6
$133 total
Sep 5 - Sep 6
Total with taxes and fees
Woodspring Suites Sumter Near Shaw Afb
Hyatt Place Sumter / Downtown

Hyatt Place Sumter / Downtown

3 out of 5
18 N Main St, Sumter, SC
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Sep 14 to Sep 15
$123 total
Sep 14 - Sep 15
Total with taxes and fees
Hyatt Place Sumter / Downtown
Tru by Hilton Sumter

Tru by Hilton Sumter

2.5 out of 5
2607 Broad Street, Sumter, SC
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Sep 14 to Sep 15
$119 total
Sep 14 - Sep 15
Total with taxes and fees
Tru by Hilton Sumter
See all 79 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.

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Frequently asked questions

How much does an Oakland vacation package cost?
You can grab a vacation package to this popular destination from $452 on Expedia. But how much your vacation to Oakland costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Oakland?
If you're hoping to snag a cheap Oakland vacation package, consider traveling in October, November and December. You'll typically find better prices on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Oakland?
Generally, a handful of days is enough to visit the top sights during your Oakland vacation. But if you prefer to have time to rest or take day tours, consider extending your trip.
How to find the best Oakland package deals?
Use Expedia's handy filters to help you find some terrific Oakland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Oakland package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
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 stays and flights individually. Better still, you can personalize your Oakland trip to fit your exact needs. Pick 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 an impromptu Oakland adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Oakland break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.