Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

10.0 out of 10, Exceptional, (2)
"Absolutely loved our visit!! Clean, cozy, and just the right size for our family of four. "
United States
Coreen M.
The price is NZ$576
includes taxes & fees
2 Jan - 3 Jan 2026
House 2.6 miles from Ole Miss + 3 miles to The Square + King Beds + Remodeled
9.6 out of 10, Exceptional, (5)
"Nice property "
United States
Christina M.
The price is NZ$448
includes taxes & fees
4 Jan - 5 Jan 2026
The Colonel's Cottage, 2BR by Velvet Ditch Villas
The price is NZ$140
includes taxes & fees
1 Jan - 2 Jan 2026
campground,fishing pond/farm petting and feeding, bright stars/fruit trees fire
The price is NZ$448
includes taxes & fees
4 Jan - 5 Jan 2026
The 1848, 2BR Condo by Velvet Ditch Villas
10.0 out of 10, Exceptional, (3)
"Loved everything about this house and our stay. Quiet, cozy, well equipped and great communication with management. "
United States
Janet S.
The price is NZ$553
includes taxes & fees
1 Jan - 2 Jan 2026
The Carl, 2BR Townhome by Velvet Ditch Villas
10.0 out of 10, Exceptional, (12)
"Very rural but very comfortable. "
United States
Phil S.
The price is NZ$422
includes taxes & fees
1 Jan - 2 Jan 2026
Tiny Home close to Ole Miss / Lake
The price is NZ$251
includes taxes & fees
1 Jan - 2 Jan 2026
Animal Farm Experience, 3-bedroom (2 qn 1 kg) rv home in the Valley
10.0 out of 10, Exceptional, (4)
"THE CABIN WAS AMAZING!! THE VEIWS FROM THE BACK PORCH WAS ABSOLUTELY BREATH TAKING!THE CABIN WAS VERY NICE AND CLEAN. CAN'T WAIT TO GO BACK!"
United States
JANNIE T.
The price is NZ$426
includes taxes & fees
31 Jan - 1 Feb 2026
2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
2.0 star property
The price is NZ$355
includes taxes & fees
4 Jan - 5 Jan 2026
The Rebel Sole in Oxford
2.0 star property
The price is NZ$355
includes taxes & fees
4 Jan - 5 Jan 2026
The Grove Sole in Oxford
9.2 out of 10, Wonderful, (5)
"We had an absolutely wonderful experience at this VRBO! From the moment we arrived, everything was exactly as described- clean, welcoming, and thoughtfully prepared. The home was spotless and well stocked with everything we needed for a comfortable stay. "
United States
Robert C.
The price is NZ$553
includes taxes & fees
1 Jan - 2 Jan 2026
The Collegiate, 2BR Cozy Stay by VelvetDitchVillas
10.0 out of 10, Exceptional, (37)
"Wonderful place and hosts "
United States
Sonya V.
The price is NZ$634
includes taxes & fees
3 Jan - 4 Jan 2026
Cabin in the woods overlooking Grenada lake.
The price is NZ$592
includes taxes & fees
8 Jan - 9 Jan 2026
The Cross Creek, Cozy 3BR by Velvet Ditch Villas

Holiday Home in Sardis

Magnolia Estate Container Home
9.4 out of 10, Exceptional, (3)
"Very cozy space with an amazing view. Very clean and open space. "
United States
jeremy l.
The price is NZ$402
includes taxes & fees
25 Jan - 26 Jan 2026
Magnolia Estate Container Home
2.0 star property
The price is NZ$457
includes taxes & fees
5 Jan - 6 Jan 2026
Hotty Toddy Headquarters
10.0 out of 10, Exceptional, (8)
"Beautiful place! Very clean and is equipped with everything you need. The hosts had great communication throughout our stay. Would highly recommend and will definitely be staying again in the future! "
United States
Shayna
The price is NZ$418
includes taxes & fees
3 Jan - 4 Jan 2026
Minutes away from one of the greatest crappie fishing lakes in the world
2.0 star property
The price is NZ$514
includes taxes & fees
4 Jan - 5 Jan 2026
Family - Friendly Oxford Retreat Near University
The price is NZ$576
includes taxes & fees
2 Jan - 3 Jan 2026
The Pappy, 2BR House by Velvet Ditch Villas
2.0 star property
The price is NZ$474
includes taxes & fees
5 Jan - 6 Jan 2026
The Lake House - Cypress Woods Place
9.8 out of 10, Exceptional, (12)
"We really enjoyed our stay at. The getaway Place was fully stocked and exceptionally clean, we expect to visit again in the fall and will definitely book this place again. ! Host is great, responded to questions almost immediately."
United States
David S.
The price is NZ$632
includes taxes & fees
31 Jan - 1 Feb 2026
The Get-A-Way at Grenada lake
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.
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Top Oakland Hotel Reviews

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as NZ$251 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay. Oakland is known for its parks.

What are some of the best holiday rentals that Oakland has to offer?

Waterfront property located at Point Pleasant on Enid Lake: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as an arcade/games room. Another good choice for your trip to Oakland is Rustic Retreat at Enid Lake.

How many holiday rentals will I find in Oakland?

Expedia has 3 holiday rentals for your stay in Oakland.

What’s there to see and do in Oakland?

George Payne Cossar State Park and Enid Lake are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Persimmon Hill Recreation Area and Wallace Creek Recreation Area.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family gatherings.