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Featured Holiday Homes in Oakland City

Vibrant and art-filled retreat, perfect for families and small groups.

Vibrant and art-filled retreat, perfect for families and small groups.

2 out of 5
Evansville
With a stay at this vacation home in Evansville, you'll be within a 10-minute drive of Ford Center and Olmstead Park.
Vibrant and art-filled retreat, perfect for families and small groups.
Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota

Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota

Evansville
When you stay at this property in Evansville, you'll be within a 10-minute drive of McCutchanville Park and Bridlewood Park.
Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Huntingburg
With a stay at this vacation home in Huntingburg, you'll be within a 5-minute drive of Market Street Park and Charles Niehaus Memorial Park.
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
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THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

2 out of 5
Lynnville
With a stay at this vacation home in Lynnville, you'll be 25.5 mi (41 km) from Holiday World and Splashin' Safari and 26.9 mi (43.3 km) from Ford Center.
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Cozy Bungalow in a nice friendly neighborhood

Cozy Bungalow in a nice friendly neighborhood

Evansville
With a stay at this vacation home in Evansville, you'll be within a 10-minute drive of Ford Center and University of Evansville.
Cozy Bungalow in a nice friendly neighborhood
Near Hiking & Fishing: Dale Home w/ Deck!

Near Hiking & Fishing: Dale Home w/ Deck!

Dale
When you stay at this vacation home in Dale, you'll be on the waterfront and 12 minutes by car from Mill Park.
Near Hiking & Fishing: Dale Home w/ Deck!
The Potter Cottage -A great family getaway 3 miles from Holiday World

The Potter Cottage -A great family getaway 3 miles from Holiday World

Ferdinand
Located in Ferdinand, this vacation home is in a rural location, within a 10-minute drive of Santa Claus Museum and 1935 Santa Statue.
The Potter Cottage -A great family getaway 3 miles from Holiday World
The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World

Gentryville
With a stay at this vacation home in Gentryville, you'll be within a 15-minute drive of Holiday World and Splashin' Safari and Lincoln State Park.
The Family Oasis just 6 miles from Holiday World
Mid-Century Brick Bungalow Home

Mid-Century Brick Bungalow Home

Evansville
With a stay at this vacation home in Evansville, you'll be within a 10-minute drive of Ford Center and Gattitown Evansville Indiana Pizza & Family Entertainment ...
Mid-Century Brick Bungalow Home
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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 City 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 City vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland City 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 City 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 City adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland City 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 City 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 City Holiday Homes essential information

Accommodation
67 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Vibrant and art-filled retreat, perfect for families and small groups., Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota, Spacious 1450 sf 2 BR Private Suite w/Dog Fe, THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water, Cozy Bungalow in a nice friendly neighborhood, Near Hiking & Fishing: Dale Home w/ Deck!, The Potter Cottage -A great family getaway 3 miles from Holiday World, The Family Oasis just 6 miles from Holiday World, Mid-Century Brick Bungalow Home

Top trending hotels in Oakland City

Walk to Oakland City University: Modern Apartment!

Walk to Oakland City University: Modern Apartment!

3 out of 5
Oakland City
When you stay at this apartment in Oakland City, you'll be 14 minutes by foot from Oakland City University.
Walk to Oakland City University: Modern Apartment!
Oakland City Apartment: Close to Dtwn

Oakland City Apartment: Close to Dtwn

3 out of 5
Oakland City
When you stay at this apartment in Oakland City, you'll be 14 minutes by foot from Oakland City University.
Oakland City Apartment: Close to Dtwn
Golf Course Views: Oakland City Retreat

Golf Course Views: Oakland City Retreat

3 out of 5
Oakland City
When you stay at this cottage in Oakland City, you'll be 14 minutes by foot from Oakland City University.
Golf Course Views: Oakland City Retreat
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< 1 Mi to Oakland City University: Cozy Apartment

< 1 Mi to Oakland City University: Cozy Apartment

3 out of 5
Oakland City
When you stay at this apartment in Oakland City, you'll be 14 minutes by foot from Oakland City University.
< 1 Mi to Oakland City University: Cozy Apartment
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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.