Book Holiday Homes in Oakland City

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Featured Holiday Homes in Oakland City

Nature’s Retreat with Game Room | Hot Tub | Sauna

Nature’s Retreat with Game Room | Hot Tub | Sauna

2 out of 5
Evansville
Book a stay at this family-friendly vacation home in Evansville. Enjoy free WiFi, a sauna, and a garden. Popular attractions Highland Baseball Park and Moutoux ...
Nature’s Retreat with Game Room | Hot Tub | Sauna
Chestnut Street Retreat

Chestnut Street Retreat

Huntingburg
Book a stay at this family-friendly vacation home in Huntingburg. Enjoy free WiFi, a garden, and patios. Popular attractions Niehaus Disc Golf Course and Huntingburg ...
Chestnut Street Retreat
Cozy Bungalow in a nice friendly neighborhood

Cozy Bungalow in a nice friendly neighborhood

Evansville
Stay at this vacation home in Evansville. Enjoy free WiFi, a garden, and patios. Popular attractions Ford Center and Wesselman Woods Nature Preserve are located ...
Cozy Bungalow in a nice friendly neighborhood
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Another Oasis just 6 miles from Holiday World

Another Oasis just 6 miles from Holiday World

Gentryville
Stay at this vacation home in Gentryville. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Colonel William Jones Home and Antique Shak ...
Another Oasis just 6 miles from Holiday World
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
Stay at this vacation home in Lynnville. Enjoy free WiFi, patios, and an in-room coffeemaker.
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
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
The price is NZ$292 per night from 16 Apr to 17 Apr
NZ$292
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Evansville. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Ford Center and Olmstead Park are located ...
Vibrant and art-filled retreat, perfect for families and small groups.
The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World

Gentryville
Stay at this vacation home in Gentryville. Enjoy a picnic area, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Colonel William Jones ...
The Family Oasis just 6 miles from Holiday World
Tranquil Hideaway: Your Private Lakefront Retreat

Tranquil Hideaway: Your Private Lakefront Retreat

Dale
The price is NZ$387 per night from 18 Apr to 19 Apr
NZ$387
includes taxes & fees
18 Apr - 19 Apr
Stay at this vacation home in Dale. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attraction Mill Park is located nearby.
Tranquil Hideaway: Your Private Lakefront Retreat
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Huntingburg
The price is NZ$367 per night from 6 Apr to 7 Apr
NZ$367
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this family-friendly vacation home in Huntingburg. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions ...
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
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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
65 Holiday Homes
Lowest Price
NZ$141
Highest Price
NZ$387
Popular accommodation
Nature’s Retreat with Game Room | Hot Tub | Sauna, Chestnut Street Retreat, Cozy Bungalow in a nice friendly neighborhood, Another Oasis just 6 miles from Holiday World, THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water, Vibrant and art-filled retreat, perfect for families and small groups., The Family Oasis just 6 miles from Holiday World, Tranquil Hideaway: Your Private Lakefront Retreat, Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Top trending hotels in Oakland City

Spark by Hilton Evansville East, IN

Spark by Hilton Evansville East, IN

2.5 out of 5
8005 E Division St, Evansville, IN
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 13 Apr to 14 Apr
NZ$154
includes taxes & fees
13 Apr - 14 Apr
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Spark by Hilton Evansville East, IN
Hampton Inn Evansville

Hampton Inn Evansville

2.5 out of 5
8000 Eagle Crest Boulevard, Evansville, IN
Fully refundableReserve now, pay when you stay
The price is NZ$141 per night from 20 Apr to 21 Apr
NZ$141
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hampton Inn Evansville
Country Inn & Suites by Radisson, Evansville, IN

Country Inn & Suites by Radisson, Evansville, IN

3 out of 5
301 Circle Front Dr, Evansville, IN
Fully refundable
The price is NZ$159 per night from 20 Apr to 21 Apr
NZ$159
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3-star business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Country Inn & Suites by Radisson, Evansville, IN
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Comfort Inn & Suites Evansville Airport

Comfort Inn & Suites Evansville Airport

2.5 out of 5
3901 Highway 41 N., Evansville, IN
Fully refundableReserve now, pay when you stay
The price is NZ$167 per night from 20 Apr to 21 Apr
NZ$167
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Evansville Airport
Don't see what you're looking for?
See all available properties in Oakland City
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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.