Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Sardis Lakefront Cabin

Sardis Lakefront Cabin

Sardis
Located in Sardis, this vacation home is on a lake, a 1-minute drive from Cypress Point Public Use Area and 5 minutes from Engineer Point Public Use Area.
Opens in a new windowSardis Lakefront Cabin
Royal Rebel Retreat: Charming Basement VRBO in Oxford, MS

Royal Rebel Retreat: Charming Basement VRBO in Oxford, MS

Oxford, MS
The price is AU$374 per night from 30 Sept to 1 Oct
AU$374
30 Sept - 1 Oct
includes taxes & fees
With a stay at this vacation home in Oxford (Royal Oaks), you'll be a 5-minute drive from University of Mississippi and 5 minutes from South Campus Rail ...
Opens in a new windowRoyal Rebel Retreat: Charming Basement VRBO in Oxford, MS
Charming 2-bedroom house in Oxford, MS

Charming 2-bedroom house in Oxford, MS

Oxford, MS
With a stay at this vacation home in Oxford, you'll be a 5-minute drive from University of Mississippi and 5 minutes from South Campus Rail Trail.
Opens in a new windowCharming 2-bedroom house in Oxford, MS
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Waterfront property located at Point Pleasant on Enid Lake

Waterfront property located at Point Pleasant on Enid Lake

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront and within a 5-minute drive of Point Pleasant Recreation Area.
Opens in a new windowWaterfront property located at Point Pleasant on Enid Lake
Rustic Retreat at Enid Lake

Rustic Retreat at Enid Lake

Oakland
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of George Payne Cossar State Park and Long Branch Recreation Area.
Opens in a new windowRustic Retreat at Enid Lake
4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful

Coffeeville
The price is AU$1,418 per night from 30 Sept to 1 Oct
AU$1,418
30 Sept - 1 Oct
includes taxes & fees
Located in Coffeeville, this vacation home is a 2-minute drive from Grenada Lake and 9 minutes from South Graysport Public Use Area.
Opens in a new window4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful
Cozy Oxford Townhouse, Close to Campus

Cozy Oxford Townhouse, Close to Campus

Oxford
With a stay at this vacation home in Oxford, you'll be within a 5-minute drive of University of Mississippi and South Campus Rail Trail.
Opens in a new windowCozy Oxford Townhouse, Close to Campus
3-bedroom house in peaceful Water Valley with AC, WiFi. Enjoy your stay

3-bedroom house in peaceful Water Valley with AC, WiFi. Enjoy your stay

Water Valley
The price is AU$431 per night from 9 Oct to 10 Oct
AU$431
9 Oct - 10 Oct
includes taxes & fees
When you stay at this vacation home in Water Valley, you'll be 5 minutes by car from Water Valley Landing Recreation Area.
Opens in a new window3-bedroom house in peaceful Water Valley with AC, WiFi. Enjoy your stay
Spacious 3 br home with large covered deck

Spacious 3 br home with large covered deck

Batesville
Located in Batesville, this vacation home is on a lake, within a 15-minute drive of Pats Bluff Public Use Area and Coles Point Public Use Area.
Opens in a new windowSpacious 3 br home with large covered deck
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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.

Oakland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakland Holiday Homes essential information

Accommodation
122 Holiday Homes
Lowest Price
AU$374
Highest Price
AU$1,418
Popular accommodation
Sardis Lakefront Cabin, Royal Rebel Retreat: Charming Basement VRBO in Oxford, MS, Charming 2-bedroom house in Oxford, MS, Waterfront property located at Point Pleasant on Enid Lake, Rustic Retreat at Enid Lake, 4-bedroom Lakehouse literally a minute to Grenada Lake Salt Water Pool Beautiful, Cozy Oxford Townhouse, Close to Campus, 3-bedroom house in peaceful Water Valley with AC, WiFi. Enjoy your stay, Spacious 3 br home with large covered deck

Top trending hotels in Oakland

Waterfront property located at Point Pleasant on Enid Lake

Waterfront property located at Point Pleasant on Enid Lake

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront and within a 5-minute drive of Point Pleasant Recreation Area.
Opens in a new windowWaterfront property located at Point Pleasant on Enid Lake
Rustic Retreat at Enid Lake

Rustic Retreat at Enid Lake

Oakland
Located in Oakland, this vacation home is on a lake, within a 15-minute drive of George Payne Cossar State Park and Long Branch Recreation Area.
Opens in a new windowRustic Retreat at Enid Lake
Enid Lake Waterfront Cabin- Point Pleasant

Enid Lake Waterfront Cabin- Point Pleasant

Oakland
When you stay at this cabin in Oakland, you'll be on the waterfront and within a 5-minute drive of Point Pleasant Recreation Area.
Opens in a new windowEnid Lake Waterfront Cabin- Point Pleasant
Save an average of 15% on thousands of hotels when you're signed in
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
Located in Oakland, this cabin is on a lake, within a 15-minute drive of George Payne Cossar State Park and Long Branch Recreation Area.
Opens in a new windowHidden Treasure at Enid Lake-Crappie Fishing, Duck Hunting, ATVRiding, Ole Miss
Don't see what you're looking for?
See all available properties in Oakland
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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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^Subject to availability and chosen travel dates.