Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Gregg Yutko

Top hotels in Oakland

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is 4.403.802 ₫ per night from 4 Mar to 5 Mar
4.403.802 ₫
6.390.724 ₫ total
4 Mar - 5 Mar
includes taxes & fees
8/10 Very Good! (9,069 reviews)
Room was clean. The AC didn’t work when we arrived but they made it right the next morning and gave resort credit which was appreciated. Hallways smelled musty and old but the room smelled clean. Food was very average at the restaurant.

Reviewed on 2 Mar 2026

The Grove Resort & Water Park Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is 3.418.810 ₫ per night from 24 Mar to 25 Mar
3.418.810 ₫
3.846.160 ₫ total
24 Mar - 25 Mar
includes taxes & fees
9.2/10 Wonderful! (4,744 reviews)
Everything was good. We cannot rate breakfast as we did not have the breakfast included. Overall everything was good

Reviewed on 1 Mar 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundable
The price is 2.756.415 ₫ per night from 29 Mar to 30 Mar
2.756.415 ₫
3.100.968 ₫ total
29 Mar - 30 Mar
includes taxes & fees
8.4/10 Very Good! (6,866 reviews)
A lot of nice perks. They gave me free fresh-baked cookies when I checked in and that made my day. It's nice that there's a car rental place right there so I rented a car last minute to visit other places. It's a convenient walk to the entrance if all you're doing is Universal Studios.

Reviewed on 2 Mar 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 39,266 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 holiday package cost?
Starting from only , a holiday 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 holiday package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1null000null000 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 travellers.
How far in advance should I book my Oakland holiday?
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 travelling 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 holiday rentals like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with an Oakland Expedia holiday 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 holiday package?
You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Oakland holiday 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.

Popular places to visit

Flamingo Crossings Town Center

You can find the perfect gifts to bring home at Flamingo Crossings Town Center during your stay in Winter Garden. Discover the top-notch restaurants and entertainment choices in this walkable area.

Flamingo Crossings Town Center

Disney's Magnolia Golf Course

Enjoy a round of golf in Winter Garden at Disney's Magnolia Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Magnolia Golf Course

Disney's Palm Golf Course

Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Palm Golf Course