Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to £335 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Packages with flights are ATOL protected

Your Oakland Holiday

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 holiday 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 holiday is only a few clicks away with Expedia.

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
510
Max Temp Winter
10ºC
Max Temp Summer
32ºC
Top Sights
George Payne Cossar State Park and Enid Lake

Our pick of the best Oakland Hotel Deals

Waterfront property located at Point Pleasant on Enid Lake
Waterfront property located at Point Pleasant on Enid Lake
Oakland, MS
Stay at this holiday home in Oakland. Enjoy free Wi-Fi, breakfast (surcharge) and laundry facilities. Popular attractions Point Pleasant Recreation Area and ...
9.8/10 Exceptional! (87 reviews)
Had a great time
"Great views comfortable beds. Host was really nice and accommodating."

Reviewed on 24 Jun 2025

Waterfront property located at Point Pleasant on Enid Lake
Rustic Retreat at Enid Lake
Rustic Retreat at Enid Lake
Oakland, MS
Stay at this holiday home in Oakland. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions George Payne Cossar State Park and ...
9.8/10 Exceptional! (22 reviews)
Blessed
"Beautiful"

Reviewed on 17 May 2025

Rustic Retreat at Enid Lake
Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping
Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping
Oakland, MS
Stay at this cabin in Oakland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Long Branch Recreation Area and Point Pleasant Recreation ...
9.2/10 Wonderful! (39 reviews)
Great place for fishing and relaxing
"This was our second stay at The Honey Hole and everything was great. Everything we needed was available and the parking for the boats was an added plus."

Reviewed on 30 Apr 2025

Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping
See all 258 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Oakland holiday with Expedia?
Expedia has you covered for every detail of your Oakland holiday. You'll always get the best deals around, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you'll score even more savings. Keen to really make the most of your stay? Add a few fun tours and activities to your package. We offer flexible cancellation policies on most bookings, so there's no need to stress if your travel plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Oakland?
If you want to experience the vibe of Oakland in peak season, book your trip for May, June and September. April, July and November are generally the quietest months of the year. With daytime average temperatures of 6ºC, January is the coolest month in Oakland. The warmest month is July, when you can experience averages of 27ºC during the day. Whatever the weather conditions, you'll find plenty to keep you entertained here.
How do I get a cheap holiday to Oakland?
Bundle your flights and hotels, add on extras such as tours, and save with an Oakland holiday. You won't just walk away with impressive discounts on your trip --- you'll have plenty of choice too. When you book through Expedia, you can choose from more than 400 air carriers and 321,000 properties around the globe. Your unforgettable holiday starts right here, right now! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Oakland holiday?
Immersing yourself in the sights is a must for any holiday in Oakland. A couple of leading attractions are Enid Lake and George Payne Cossar State Park. If you've time to explore more, check out other notable sights here.
What is the best area to stay in when on holiday in Oakland?
There's loads to do in Oakland, so spend your nights near its best attractions and treat yourself to more time sightseeing. Enid Lake is one place to add to your to-do list.
Do I need a visa for my Oakland holiday?
Visa requirements for Oakland vary depending on your nationality and the reason for your visit. Remember to check official government websites to determine if you need a visa for your trip. They'll also give you the most up-to-date information, including details about application procedures or any supporting documentation that might be necessary. Enquire about your visa requirements well ahead of time to ensure a travel experience that's hassle free. Finally, check to see that your passport has at least six months validity from your planned return date.
What should I wear on my Oakland holiday?
Though everyone's personal style differs, it can be useful to have a few guidelines for what to wear on your holiday in Oakland. Think about browsing style blogs before you go for inspiration on local fashion trends. Daytime temperatures in January, Oakland's coolest month, are around 6ºC. July marks this city's warmest month when the average daily temperature reaches 27ºC. Our tip? Take the guesswork out of packing and check the weather forecast.
What does an Expedia Oakland holiday include?
It all comes down to what type of getaway you're thinking about. Oakland holiday deals can include car hires, hotels and flights. You can mix and match to find the travel package that works for you! You can also add on activities and experiences after you've booked to get even bigger discounts. Expedia features all types of properties, with the most popular in Oakland being private holiday homes and cabins. With Expedia, you can expect the freedom and flexibility to customise your holiday your way.
Does Expedia offer Book Now, Pay Later Oakland holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book an incredible getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying over multiple transactions sounds right for you, choose this option during the checkout process.
  • No-deposit holidays: Pressing the "book now" button is easier with this option. With no deposit required for your escape, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with an Oakland Expedia holiday?
Most definitely. Expedia has over 400 partner airlines to pick from globally. With all that choice, finding the ideal carrier to get you to Oakland will be a breeze.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.