Oakland Vacations

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Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Waterfront property located at Point Pleasant on Enid Lake

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

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Waterfront property located at Point Pleasant on Enid Lake
Hidden Treasure at Enid Lake-Crappie Fishing, Duck Hunting, ATVRiding, Ole Miss

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

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Hidden Treasure at Enid Lake-Crappie Fishing, Duck Hunting, ATVRiding, Ole Miss
Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping

Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping

Oakland MS
9.4/10 Exceptional! (41 reviews)
"Property was suitable for our needs. There was an issue with towels, however that was rectified. There were some cleanliness issues. All of the kitchen counters were filthy upon arrival and the refrigerator had not been cleaned for some time. The kitchen sink was leaking in the cabinet underneath ..."

Reviewed on Apr 11, 2026

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Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping
See all 311 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.

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.
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Frequently asked questions

How much does an Oakland vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Oakland costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Oakland?
Plan your getaway for the shoulder or low season and you're likely to score cheap Oakland vacation packages. Bear in mind that public holidays and major festivals and events can have an impact on prices, so do some research before you go.
How many days is enough for Oakland?
The ideal duration for your Oakland vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you time to go to all the main sights and explore some hidden treasures along the way.
How to find the best Oakland package deals?
Finding a cheap Oakland package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Oakland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations separately. Better still, you can customize your Oakland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland?
If you're planning a spontaneous Oakland trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Oakland?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the available activities will also help you decide when to vacation in Oakland.
  2. Plan your budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that may come up during your trip to Oakland.
  3. Decide your trip length: Consider how long you'd like to spend discovering Oakland. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Oakland vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.