Oakland, MS

Travel Guide

Waterfront property located at Point Pleasant on Enid Lake

Waterfront property located at Point Pleasant on Enid Lake

Oakland MS
Stay at this vacation home in Oakland. Enjoy free WiFi, breakfast (surcharge), and laundry facilities. Popular attractions Point Pleasant Recreation Area and ...
9.8/10 Exceptional! (100 reviews)
"Our 45th Anniversary could not of been any better…. 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 Aug 29, 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
Stay at this cabin in Oakland. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions George Payne Cossar State Park and Long ...
9.2/10 Wonderful! (36 reviews)
"Perfect place for a trip up to an ole Miss game. Good vibes"

Reviewed on Oct 25, 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
Stay at this cabin in Oakland. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Point Pleasant Recreation Area and Chickasaw Hill Recreation ...
10/10 Exceptional! (29 reviews)
"The view is outstanding. You clearly see the lake. The cabin can easily accommodate a large family. I would recommend the cabin to anyone looking for a place to relax and get away."

Reviewed on Oct 13, 2026

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Enid Lake Waterfront Cabin- Point Pleasant
See all 349 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.
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
Stay at this cabin in Oakland. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions George Payne Cossar State Park and Long ...
9.2/10 Wonderful! (36 reviews)
"Perfect place for a trip up to an ole Miss game. Good vibes"

Reviewed on Oct 25, 2026

Hidden Treasure at Enid Lake-Crappie Fishing, Duck Hunting, ATVRiding, Ole Miss
The Sac Au Lait Chalet

The Sac Au Lait Chalet

Oakland MS
Stay at this cabin in Oakland. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions George Payne Cossar State Park and ...
9.8/10 Exceptional! (8 reviews)
"Cozy and comfortable. We were very comfortable. Thoroughly enjoyed this cabin. Great place to stay while visiting Oxford and Ole Miss."

Reviewed on Sep 25, 2026

The Sac Au Lait Chalet
Waterfront property located at Point Pleasant on Enid Lake

Waterfront property located at Point Pleasant on Enid Lake

Oakland MS
Stay at this vacation home in Oakland. Enjoy free WiFi, breakfast (surcharge), and laundry facilities. Popular attractions Point Pleasant Recreation Area and ...
9.8/10 Exceptional! (100 reviews)
"Our 45th Anniversary could not of been any better…. 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 Aug 29, 2026

Waterfront property located at Point Pleasant on Enid Lake
See all 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

Is Oakland worth visiting?
Oakland is worth visiting for its outdoor attractions, such as George Payne Cossar State Park and Point Pleasant Recreation Area, which offer travelers opportunities for recreation. The destination also boasts a diverse culinary scene, with excellent Asian and Latin American dining options to explore.
When is the best time to visit Oakland?
The best time to visit Oakland is from March through May, when travelers can enjoy pleasant spring weather. For fewer crowds and better value, the quieter months of December through February are a good option, offering cooler temperatures and a more relaxed atmosphere.
What is Oakland known for?
Oakland is known for its outdoor recreation, with travelers enjoying George Payne Cossar State Park, Point Pleasant Recreation Area, and Persimmon Hill Recreation Area. This city also offers a strong Asian food culture for visitors to explore.
What is a good itinerary length for Oakland?
A good itinerary length for Oakland is one to two days to explore natural spots like George Payne Cossar State Park, Point Pleasant Recreation Area, and Persimmon Hill Recreation Area. For a more relaxed trip, consider three to four days to enjoy these areas more fully and sample the local Asian, Latin American, or North American cuisine.
What are the top things to do in and around Oakland?
Oakland offers many opportunities to enjoy nature and outdoor recreation:

  • Explore George Payne Cossar State Park.
  • Visit Point Pleasant Recreation Area.
  • Discover Persimmon Hill Recreation Area.
  • Wander through Wallace Creek Recreation Area.
  • Enjoy Plum Point Recreation Area.

How do I plan a trip to Oakland?
To plan your trip to Oakland, search Expedia for hotels and book flights and rental cars in advance. You can enjoy outdoor activities at places like George Payne Cossar State Park, Point Pleasant Recreation Area, and Persimmon Hill Recreation Area; plan these for early morning or late afternoon. Also, explore the diverse Asian, Latin American, and North American dining options.
What cuisines can you find in Oakland?
In Oakland you can find Vietnamese cuisine, with dishes like pho, banh mi, and spring rolls. Travelers also have many Asian options, including Chinese, Japanese, and Thai food. You'll also find Latin American choices like Mexican, North American comfort food such as Southern soul food, and Italian specialties.
Can I book a refundable hotel in Oakland?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Oakland by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Oakland with Expedia?
Expedia makes it easier to plan your Oakland trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Oakland?
The best choice depends on your travel style. Hotels in Oakland can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Oakland trip on Expedia?
Once you've booked your Oakland trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Oakland trip?
Expedia offers customer support before, during, and after your Oakland trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Oakland?
If it's your first trip to Oakland, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Oakland hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Oakland hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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