Oakland Vacations from $519
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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
- Holiday Inn Express & Suites Columbia-I-26 @ Harbison Blvd by IHG
Jan 28 - Feb 1Holiday Inn Express & Suites Columbia-I-26 @ Harbison Blvd by IHG + Flight
Columbia4 nights2.5 star property9.0/10 - Wonderful (1,255 reviews)"Nice place."Reviewed November 6, 2026Roundtrip • New York (EWR) - Columbia (CAE)EWR - CAE • Nonstop CAE - EWR • Nonstop$564$519found 1 day agoper traveler - Hyatt Place Sumter / Downtown
Jan 17 - Jan 20Hyatt Place Sumter / Downtown + Flight
Sumter3 nights3.0 star property9.2/10 - Wonderful (986 reviews)Roundtrip • New York (EWR) - Columbia (CAE)EWR - MYR • 1 stop MYR - EWR • 1 stop$623$531found 12 hours agoper traveler - Near USC Downtown Fire Pit Dog Friendly
Jan 28 - Feb 1Near USC Downtown Fire Pit Dog Friendly + Flight
Melrose Heights4 nights2.0 star propertyRoundtrip • New York (EWR) - Columbia (CAE)EWR - CAE • Nonstop CAE - EWR • Nonstop$1,157$1,033found 1 day agoper traveler - The Mantissa Hotel
Jan 17 - Jan 20The Mantissa Hotel + Flight
Hartsville3 nights3.0 star property9.2/10 - Wonderful (317 reviews)Roundtrip • New York (EWR) - Florence (FLO)EWR - MYR • 1 stop MYR - EWR • 1 stop$643$580found 12 hours agoper traveler - Holiday Inn Express Columbia NE - Fort Jackson by IHG
Jan 28 - Feb 1Holiday Inn Express Columbia NE - Fort Jackson by IHG + Flight
Columbia4 nights2.5 star property8.6/10 - Excellent (1,002 reviews)"The hotel Was under construction. I don't mind that however , our room was maybe just completed. The elevator inspection notice was from 2024. We took the stairs, It was kind of scary to be in. The bathroom Floor wasn't tacked down. The bathroom door didn't stay closed. The toilet barely flushed. Due to construction the gym was not set up yet. I usually hit the gym everyday. Not very happy with the price point and what I recieved. 281.00 total For two nights I expected things to be in a bit..."Reviewed November 5, 2026Roundtrip • New York (EWR) - Columbia (CAE)EWR - CAE • Nonstop CAE - EWR • Nonstop$573$528found 1 day agoper traveler
Oakland Hotel Deals
"Staff was great. Location is fantastic with respect to proximity to dining options. My two greatest complaints are that the in-room wifi was absolutely horrible and the bed was NOISY!!!! I had to go out to McDonalds & Chick-Fil-A to get wifi that allowed me to work. Everytime I rolled over on the bed, I could hear the metal bedframe/springs squeaking & shifting."
Quality Inn Sumter near Shaw AFB
Quality Inn Sumter near Shaw AFB"Just don't unless it's like $30/night. That's where your expectations should be."
"First of all the photos online ARE NOT the photos of this hotel. I had a room with two queen beds in it. The mattress was more like a box spring and each queen size bed had one 1/2 thick pillow, i had to go biy some pillows. The water going into the bathtub was brown. The weed smoke out in front of my door was so thick u could cut it. The owner kept questioning me if I had more than two people, cuz if I did I had to pay 20$ per person"
Comfort Suites Sumter near Shaw AFB
Comfort Suites Sumter near Shaw AFB
"The rooms in the hotel were pretty bare bones and crowded. Ours had 2 fridges (one large) and no microwave...?? The pool was also very basic--no changing rooms or spa. The breakfast was very good and the staff were pleasant and very helpful. In-room amenities were limited (no closets, no tea/coffee in the room, only very bright overhead lights), but thought had been given to providing access in the lobby to replace some--round the clock tea/coffee, a pool table, kids' toys, individual little...
Frequently Asked Questions
How much does an Oakland vacation package cost?
You can grab a vacation package to this popular destination from $519 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.