Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Bougie Residence in a Country Setting near Enid and Grenada Lake

Bougie Residence in a Country Setting near Enid and Grenada Lake

Grenada MS
Located in Grenada, this vacation home is in a rural location, within a 15-minute drive of Williams Lake and Lee Tartt Nature Preserve.
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Opens in a new windowBougie Residence in a Country Setting near Enid and Grenada Lake
Spacious 3 br home with large covered deck

Spacious 3 br home with large covered deck

Batesville MS
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.
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Opens in a new windowSpacious 3 br home with large covered deck
Sardis Lakefront Cabin

Sardis Lakefront Cabin

Sardis MS
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.
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Opens in a new windowSardis Lakefront Cabin
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Cozy Oxford Townhouse, Close to Campus

Cozy Oxford Townhouse, Close to Campus

Oxford MS
With a stay at this vacation home in Oxford, you'll be within a 5-minute drive of South Campus Rail Trail and Baptist Memorial Hospital-North Mississippi.
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Opens in a new windowCozy Oxford Townhouse, Close to Campus
Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake

Grenada MS
The price is AU$407 per night from 26 Mar to 27 Mar
AU$407
26 Mar - 27 Mar
includes taxes & fees
Located in Grenada, this vacation home is in a rural location, within a 10-minute drive of Grenada Country Club and Perry Creek Golf & Racquet Club.
Opens in a new windowLida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
Charming 1940's ranch home on Hwy 6, minutes from the Grove and downtown Oxford.

Charming 1940's ranch home on Hwy 6, minutes from the Grove and downtown Oxford.

Oxford MS
With a stay at this vacation home in Oxford, you'll be within a 15-minute drive of South Campus Rail Trail and University of Mississippi.
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Opens in a new windowCharming 1940's ranch home on Hwy 6, minutes from the Grove and downtown Oxford.
Recently Renovated Vacation Rental Close to Campus

Recently Renovated Vacation Rental Close to Campus

Oxford MS
Located in Oxford, this vacation home is within a 5-minute drive of South Campus Rail Trail and Baptist Memorial Hospital-North Mississippi.
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Opens in a new windowRecently Renovated Vacation Rental Close to Campus
One block from Main Street, short ride to Oxford, Enid, Sardis and Grenada Lakes

One block from Main Street, short ride to Oxford, Enid, Sardis and Grenada Lakes

Water Valley MS
The price is AU$429 per night from 23 Apr to 24 Apr
AU$429
23 Apr - 24 Apr
includes taxes & fees
With a stay at this vacation home in Water Valley, you'll be a short 5-minute walk from Railroad Park and within 2 minutes by car from City Park.
Opens in a new windowOne block from Main Street, short ride to Oxford, Enid, Sardis and Grenada Lakes
Cabin in the woods overlooking Grenada lake.

Cabin in the woods overlooking Grenada lake.

Coffeeville MS
The price is AU$520 per night from 3 Apr to 4 Apr
AU$520
3 Apr - 4 Apr
includes taxes & fees
Located in Coffeeville, this vacation home is on the waterfront, a 4-minute drive from Grenada Lake and 10 minutes from South Graysport Public Use Area.
Opens in a new windowCabin in the woods overlooking Grenada lake.
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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
110 Holiday Homes
Lowest Price
AU$407
Highest Price
AU$520
Popular accommodation
Bougie Residence in a Country Setting near Enid and Grenada Lake, Spacious 3 br home with large covered deck, Sardis Lakefront Cabin, Cozy Oxford Townhouse, Close to Campus, Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake, Charming 1940's ranch home on Hwy 6, minutes from the Grove and downtown Oxford., Recently Renovated Vacation Rental Close to Campus, One block from Main Street, short ride to Oxford, Enid, Sardis and Grenada Lakes, Cabin in the woods overlooking Grenada lake.

Top trending hotels in Oakland

Waterfront property located at Point Pleasant on Enid Lake

Waterfront property located at Point Pleasant on Enid Lake

Oakland MS
When you stay at this vacation home in Oakland, you'll be on the waterfront and within a short 4-minute drive from Point Pleasant Recreation Area.
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Opens in a new windowWaterfront 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
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.
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Opens in a new windowHidden 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
When you stay at this cabin in Oakland, you'll be on the waterfront and within a short 4-minute drive from Point Pleasant Recreation Area.
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Opens in a new windowEnid Lake Waterfront Cabin- Point Pleasant
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Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping

Crappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping

Oakland MS
Located in Oakland, this cabin is in a rural location, within a 10-minute drive of George Payne Cossar State Park and Long Branch Recreation Area.
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Opens in a new windowCrappie Fishing, Hunting, ATV Trails, Boating, Fishing, State Park, Camping
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.