Oakland Vacation Packages
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Your Oakland Vacation
You'll find plenty to love about Oakland, from its rich history to its friendly locals. When you're ready to spend a bit of time in this fascinating city, our Oakland vacation packages will be just the ticket. Your trip to Oakland wouldn't be complete without seeing its top attractions, starting with George Payne Cossar State Park. Don't put off visiting this destination any longer. Your dream Oakland vacation is only a few clicks away with Expedia.
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Waterfront property located at Point Pleasant on Enid Lake
Oakland MS
9.8/10 Exceptional! (99 reviews)
"Absolutely stunning views, clean, peaceful, relaxing. The bed was incredibly comfortable and since this stay was intended for nothing BUT rest and relaxation, couldn't have asked for ANY improvement!"
Reviewed on Jun 28, 2026
Hidden Treasure at Enid Lake-Crappie Fishing, Duck Hunting, ATVRiding, Ole Miss
Oakland MS
9.4/10 Exceptional! (33 reviews)
"Really could do something with all three of the grills on the property as none were usable, I had to go and purchase one for use during the trip. Back porch was a disaster .. we spend a majoriy of our time outdoors when we come over that way so.. inside was doable ."
Reviewed on Jun 26, 2026
Rustic Retreat at Enid Lake
Oakland MS
9.6/10 Exceptional! (25 reviews)
"great weekend stay close to the lake."
Reviewed on Oct 10, 2025
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.
Stay near popular Oakland attractions
George Payne Cossar State Park
7.6/10 (20 reviews)
You can take time to visit George Payne Cossar State Park during your travels to Oakland. You can enjoy the bars while in the area.
Point Pleasant Recreation Area
Explore the great outdoors at Point Pleasant Recreation Area, a lovely green space in Oakland. While you're in the area, wander around the parks.
Persimmon Hill Recreation Area
Explore the great outdoors at Persimmon Hill Recreation Area, a lovely green space in Oakland. While you're in the area, wander around the parks.
Wallace Creek Recreation Area
Explore the great outdoors at Wallace Creek Recreation Area, a lovely green space in Oakland. While you're in the area, wander around the parks.
Plum Point Recreation Area
Explore the great outdoors at Plum Point Recreation Area, a lovely green space in Oakland. While you're in the area, wander around the parks.
Long Branch Recreation Area
Explore the great outdoors at Long Branch Recreation Area, a lovely green space in Oakland. While you're in the area, wander around the parks.
Riverview Recreation Area
Explore the great outdoors at Riverview Recreation Area, a lovely green space in Oakland. While you're in the area, wander around the parks.
Frequently asked questions
How much does an Oakland vacation package cost?
You'll find cheap prices on Expedia for your Oakland break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
To pick up cheap Oakland vacation packages, organize your getaway outside of peak periods like public holidays and major festivals. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Oakland?
The ideal duration for your Oakland vacation depends on what you'd like to do. Generally, a few days to a week will give you enough time to tick off all the top attractions and discover some hidden spots along the way.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical 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?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still get the freedom to create a personalized Oakland vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Oakland?
If you have your Oakland travel dates finalized, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Oakland?
- Pick your dates: The things you plan to do in Oakland and your favourite season will help you decide when to travel.
- Plan your budget wisely: On top of the price of your hotel, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Oakland.
- Decide how long to go away for: Now that you're more familiar with Oakland, you can work out the perfect length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find an Oakland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
