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Vacation Homes in Oakland City

Our top choices for Oakland City vacation homes

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

10.0 out of 10, Exceptional, (181)
"Easy check in, clean house, well kept, and the best-equipped kitchen. They even had seasoning salt for grilling!"
The Potter Cottage -A great family getaway 3 miles from Holiday World

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

2.0 star property
10.0 out of 10, Exceptional, (8)
"Visiting family for Easter, the property was exactly what we needed. Clean and quiet. "
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

Mid-Century Brick Bungalow Home

6.0 out of 10, (16)
"Close to everything we wanted to do."
Mid-Century Brick Bungalow Home

5 Miles from Holiday World sleeps 11+ —Family Escape

10.0 out of 10, Exceptional, (4)
5 Miles from Holiday World sleeps 11+ —Family Escape

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

9.8 out of 10, Exceptional, (18)
"It's very close to Holiday World "
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Renovated Ranch: 3BDRM 2BATH with King Bed, En-Suite, Sleeps 6, Hot Tub & more!

9.8 out of 10, Exceptional, (8)
"Great place as advertised! Only feedback: no body wash in the showers (did find a mega jug in the laundry room); lots of bird droppings on outside table. "
Renovated Ranch: 3BDRM 2BATH with King Bed, En-Suite, Sleeps 6, Hot Tub & more!

Barn in the Burgh

10.0 out of 10, Exceptional, (8)
"This place is beautiful!! It was just what we needed for a couple of days away with our two dogs. The host was quick to respond to my questions prior to booking. We will definitely be back. "
Barn in the Burgh

Relax Inn this Knotty & Nice entire Home

9.2 out of 10, Wonderful, (18)
"Visiting our daughter for Christmas. Nice comfortable house, exactly as described. Host was very responsive to questions. Highly recommend this place anytime you need a home away from home in Evansville"
Relax Inn this Knotty & Nice entire Home

Tranquil Hideaway: Your Private Lakefront Retreat

9.0 out of 10, Wonderful, (10)
"We had a peaceful time. We loved Santa Claus. Plan on making an annual trip. "
Tranquil Hideaway: Your Private Lakefront Retreat

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

9.8 out of 10, Exceptional, (30)
"Enjoyed staying in this cozy little spot and admiring the history within its walls. Would definitely consider staying here again!"
The price is SAR 368
SAR 1,044 total
includes taxes & fees
2 Oct - 3 Oct
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

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

10.0 out of 10, Exceptional, (3)
"The property is so beautiful the house is amazing. The rooms were so beautiful. The kids loved the pool. The hot tub was so relaxing. We enjoyed making s’mores it was truly amazing and relaxing experience "
Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota

Chestnut Street Retreat

10.0 out of 10, Exceptional, (43)
"Everything was great, as described on VRBO. "
Chestnut Street Retreat

Peaceful Retreat w/Backyard-3BR-Free Parking

10.0 out of 10, Exceptional, (5)
"Nicely equipped, clean, and decorated home. Centrally located. Very nice stay. Host was thoughtful to have children's plates."
Peaceful Retreat w/Backyard-3BR-Free Parking

2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!

10.0 out of 10, Exceptional, (21)
"Comfortable place to stay while enjoying g holiday world. "
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!

The Family Oasis just 6 miles from Holiday World

9.4 out of 10, Exceptional, (40)
"The place was amazing. Very nice place to stay for the weekend "
The Family Oasis just 6 miles from Holiday World

X Marks the Spot (Purple)

10.0 out of 10, Exceptional, (13)
"Excellent accommodations, extremely clean, perfect location to Holiday World."
X Marks the Spot (Purple)

X Marks the Spot(Blue)1.5 miles from Holiday World

9.8 out of 10, Exceptional, (14)
"Close to everything we wanted to do. Owner was responsive and house was stocked and clear instructions on check out."
X Marks the Spot(Blue)1.5 miles from Holiday World

Another Oasis just 6 miles from Holiday World

8.8 out of 10, Excellent, (18)
"We stayed two nights. There were 6 adults and 1 child in our group and the house was large enough to be comfortable. We had a great time!"
Another Oasis just 6 miles from Holiday World

Cozy Bungalow in a nice friendly neighborhood

9.8 out of 10, Exceptional, (70)
"This house was in a great locationand we had lots of fun"
Cozy Bungalow in a nice friendly neighborhood

X Marks the Spot(Yellow)1.5 mi. from Holiday World

9.6 out of 10, Exceptional, (13)
"Great location for a Holiday World trip"
X Marks the Spot(Yellow)1.5 mi. from Holiday World
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 City Hotel Reviews