Search Vacation Homes in Oakland City

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 65 Vacation Homes in Oakland City with updated reviews, rates, and availability.

Nature’s Retreat with Game Room | Hot Tub | Sauna
Smart TV, fireplace, foosball

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

2.0 star property
9.0 out of 10, Wonderful, (2)
"We enjoyed our weekend stay at this country p property, the house is spacious and a great place to stay if you are visiting family and/friends in Evansville and nearby areas. The house is spacious and the host was accessible. We felt like the check out time was too early compared to other places that we had stayed during our travels. "
Nature’s Retreat with Game Room | Hot Tub | Sauna
Chestnut Street Retreat
3 bedrooms, iron/ironing board, travel crib, free WiFi

Chestnut Street Retreat

10.0 out of 10, Exceptional, (34)
"We loved our stay at the home and we will definitely return again on our next trip to Huntingburg"
Chestnut Street Retreat
Cozy Bungalow in a nice friendly neighborhood
Fridge, microwave, oven, stovetop

Cozy Bungalow in a nice friendly neighborhood

10.0 out of 10, Exceptional, (63)
"Nice place, comfortable and clean."
Cozy Bungalow in a nice friendly neighborhood
Another Oasis just 6 miles from Holiday World
Exterior

Another Oasis just 6 miles from Holiday World

8.8 out of 10, Excellent, (10)
"Very close to Holiday World. Enjoyed the outdoor space and fire pit."
Another Oasis just 6 miles from Holiday World
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Interior

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, (2)
"Visiting family for Easter, the property was exactly what we needed. Clean and quiet. "
The price is AED 562
AED 1,168 total
includes taxes & fees
13 May - 14 May
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.
Property grounds

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

2.0 star property
9.6 out of 10, Exceptional, (9)
"Nice clean stay for a quick weekend and close to downtown. "
The price is AED 184
AED 655 total
includes taxes & fees
12 May - 13 May
Vibrant and art-filled retreat, perfect for families and small groups.
Tranquil Hideaway: Your Private Lakefront Retreat
Fridge, microwave, oven, stovetop

Tranquil Hideaway: Your Private Lakefront Retreat

7.4 out of 10, Good, (3)
"It was perfect place to stay! I was able to throw a few piles in the lake and catch a few crappie and bass! The host was available for any questions I had. "
The price is AED 358
AED 838 total
includes taxes & fees
25 May - 26 May
Tranquil Hideaway: Your Private Lakefront Retreat
The Family Oasis just 6 miles from Holiday World
Property grounds

The Family Oasis just 6 miles from Holiday World

9.2 out of 10, Wonderful, (33)
"The place was amazing. Very nice place to stay for the weekend "
The Family Oasis just 6 miles from Holiday World
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Fridge, microwave, oven, stovetop

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

10.0 out of 10, Exceptional, (10)
"We stayed overnight after going to Holiday World. The listing was accurate and the accommodations were clean and ready. Very enjoyable stay!"
The price is AED 489
AED 773 total
includes taxes & fees
9 May - 10 May
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Smart TV, books

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

9.8 out of 10, Exceptional, (28)
"Hosts made sure we checked in okay and were very responsive to any questions we had."
The price is AED 375
AED 1,070 total
includes taxes & fees
13 May - 14 May
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Comfort and Charm Highly Recommended
Fridge, microwave, oven, stovetop

Comfort and Charm Highly Recommended

9.6 out of 10, Exceptional, (12)
"We stayed here for a weekend and it was a pleasant stay. It was cute, charming, and a good size. The host was very communicative and left plenty of snacks for us, which was great! The house is in a great location and was presented to us in superb condition. Would highly recommend this place!"
Comfort and Charm Highly Recommended
Cozy Cottage, 3 mins from EVV, fenced yard
Interior

Cozy Cottage, 3 mins from EVV, fenced yard

10.0 out of 10, Exceptional, (12)
"It was a clean property and a nice neighborhood for my family to stay in. They had everything we need! Thank you! "
Cozy Cottage, 3 mins from EVV, fenced yard
Stylish 3-bedroom home centrally located in wonderful Evansville
Private kitchen

Stylish 3-bedroom home centrally located in wonderful Evansville

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."
Stylish 3-bedroom home centrally located in wonderful Evansville
Sweet Spot in the City
Exterior

Sweet Spot in the City

9.8 out of 10, Exceptional, (6)
"Went with my siblings and their spouses. We had an amazing time."
Sweet Spot in the City
Cozy 3BR Spacious home w/Patio -Sleeps8
Interior

Cozy 3BR Spacious home w/Patio -Sleeps8

10.0 out of 10, Exceptional, (2)
"Great house, quiet neighborhood. Home as advertised. Will book again for next visit!"
Cozy 3BR Spacious home w/Patio -Sleeps8
Barn in the Burgh
Fridge, microwave, oven, stovetop

Barn in the Burgh

10.0 out of 10, Exceptional, (3)
"Perfect for our Pre-Prom and Post-Prom event hosted by parents!!"
The price is AED 393
AED 1,189 total
includes taxes & fees
9 May - 10 May
Barn in the Burgh
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Aerial view

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

10.0 out of 10, Exceptional, (14)
"Comfortable place to stay while enjoying g holiday world. "
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
The Potter Cottage -A great family getaway 3 miles from Holiday World
Terrace/patio

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

10.0 out of 10, Exceptional, (161)
"The house was very clean on arrival and was nicely decorated! It was the perfect spot for a weekend stay. We even made the mistake of taking the Bluetooth speaker thinking our friend left it behind and the host was very understanding and we were able to get it back to them! "
The Potter Cottage -A great family getaway 3 miles from Holiday World
Mid-Century Brick Bungalow Home
Fridge, microwave, oven, stovetop

Mid-Century Brick Bungalow Home

6.2 out of 10, (10)
"Jason has a nice cozy home. "
The price is AED 459
AED 988 total
includes taxes & fees
18 May - 19 May
Mid-Century Brick Bungalow Home
River View in Downtown Newburgh
Exterior

River View in Downtown Newburgh

9.0 out of 10, Wonderful, (2)
"The views of the Ohio River were beautiful. Lots of steps up to house but the views were worth it! House was clean and neat…gorgeous furniture. Our grandchildren especially loved the games in the library room. We also loved being able to seat the whole family at dining table for meals. Lovely home. "
River View in Downtown Newburgh
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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Other property types in Oakland City

Golf, Shop, Tour & More: Oakland City Apartment
Interior

Golf, Shop, Tour & More: Oakland City Apartment

3.0 star property
Golf, Shop, Tour & More: Oakland City Apartment
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Interior

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3.0 star property
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Golf Course Views: Oakland City Retreat
Interior

Golf Course Views: Oakland City Retreat

3.0 star property
Golf Course Views: Oakland City Retreat
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.