Oakland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Oakland
Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
CA $1,201
per person
Nov 28 - Dec 5
found 6 hours ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (1,334 reviews)
Clean rooms. A lot of space for families. Friendly staff
Reviewed on Oct 16, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,835
per person
Jan 1 - Jan 8
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
This place was fantastic to stay at. We had a two bedroom cottage, the facilities were fantastic. All bedrooms ensuite, TVs in every room. Full kitchen and living room. Hot tub. Great pool nearby and sunset walk is five minutes walk away. They had live music in most nights and there is a lot of different food and drink places there.
Reviewed on Oct 15, 2026
The Delaney Hotel
South Orange
CA $1,399
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.6/10 Exceptional! (1,213 reviews)
Nice property, clean hotel! Sometimes loud, with the ambulances and helicopters going to the hospital, directly across the street. Beds are soft, so not very comfortable, wish they were more firm. Overall, nice stay though!
Reviewed on Oct 15, 2026
Oakland Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
CA $194
CA $218 total
Nov 8 - Nov 9
includes taxes & fees
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Fully refundable
CA $144
CA $161 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (7,107 reviews)
"A beautiful, comfortable, and clean hotel! Housekeeping was phenomenal and the pool and hot tub were added bonuses. The restaurant had excellent food and the ice cream shop was a nice extra stop at night. It has a convenient walkway to Universal Studios if you don't mind the hike. It probably took ..."
Reviewed on Oct 16, 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
CA $148
CA $166 total
Nov 11 - Nov 12
includes taxes & fees
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?
Starting from only CA $982, a vacation package is your portal to affordable travel. Customize your Oakland escape by picking from our great range of airfares, hotels and rental cars.
How do I get a cheap travel package to Oakland?
You'll save a ton of money if you bundle your flights, hotels and car rentals into an Oakland vacation package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 hotels worldwide, which means you'll always have plenty of options to choose from. Like to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Oakland?
With loads to explore in Oakland, we recommend you lock in a hotel near its attractions. West Orange Trail, Garden Theatre and Winter Garden Heritage Museum are some popular ones to add to your itinerary.
What are the top hotels in Oakland?
Whether you'll be staying for one night or longer in Oakland, you'll get a good night's rest at The Oak View Place. This place is the first choice for many travelers.
How far in advance should I book my Oakland vacation?
While prices change from time to time, we generally recommend booking your seats as soon as possible. Most international fares become available on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Discount prices to Oakland sometimes appear only weeks before departure.
What does an Expedia Oakland travel package include?
Rental cars, hotels and flights, or any combination of them — the choice is all yours! Whether you're exploring Oakland on a family road trip or traveling with your friends, there's a package to match your budget and style. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking an Oakland travel package?
Locking in all the parts of your getaway together is a simple way to save. Combine car rentals, airfares and hotels into a tidy package. But you're not limited to hotels. Expedia features all kinds of properties, including vacation rentals like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with an Oakland Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to pick from worldwide. With all that choice at your fingertips, finding the perfect carrier to fly you to Oakland will be a cinch.
If I'm not able to travel, can I cancel my Oakland vacation package?
You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Oakland vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, visit our Customer Service Portal for further information.
Things to do
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $196
per adult
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
CA $43
per adult
92% of travellers recommend
WonderWorks All Access After Dark
CA $39
per traveller
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.