Oakland Vacations

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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.

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Discover the most popular places to visit in Oakland

George Payne Cossar State Park

4/5(8 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.

George Payne Cossar State Park

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! (95 reviews)
Clean rooms great host

Reviewed on Jan 19, 2026

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Waterfront property located at Point Pleasant on Enid Lake
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! (40 reviews)
It's a lovely property is you want to go on a fishing trip. If you're going to Oxford to attend a football game, it's too far out, IMO. This would be a perfect place for a bunch of guys to stay for a weekend vacation.

Reviewed on Sep 22, 2025

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Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping
Enid Lake Waterfront Cabin- Point Pleasant

Enid Lake Waterfront Cabin- Point Pleasant

Oakland MS
10/10 Exceptional! (24 reviews)
Beautiful property on Enid lake. Amazing views from the porch and most of the bedroomwindows. Perfect for a large family or friends. Had plenty of cookware, a grill, fryer and outdoor seating.

Reviewed on Sep 2, 2025

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Enid Lake Waterfront Cabin- Point Pleasant
See all 277 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.

Find the Best Oakland Vacation Packages

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
510
Top Sights
George Payne Cossar State Park and Enid Lake

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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?
If you're looking to score a cheap Oakland vacation package, consider traveling in April, July and November. You're likely to find better prices on airfares and hotels during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Oakland?
Usually, a handful of days is enough to check out the top attractions during your Oakland vacation. But if you'd like to have time to kick back or go on day tours, think about extending your trip.
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.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Secure your dream trip to Oakland with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for the next payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.