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! (100 reviews)
"Our 45th Anniversary could not of been any betterā€¦. the VIEW with the breeze, the beautiful and comfortable bed. Any amenity needed was here, all the lovely furniture and decorations - just enough. We lived on the deck. Thanks for the memories!"

Reviewed on 29 August 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
9.2/10 Wonderful! (36 reviews)
"Perfect place for a trip up to an ole Miss game. Good vibes"

Reviewed on 25 October 2026

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

Enid Lake Waterfront Cabin- Point Pleasant

Oakland MS
10/10 Exceptional! (32 reviews)
"Amazing host and property!!"

Reviewed on 10 November 2026

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Enid Lake Waterfront Cabin- Point Pleasant
See all 354 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?
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 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 traveling 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 favorite 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?

  1. Pick your dates: The things you plan to do in Oakland and your favorite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.