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Compare 55 Vacation Homes in Oakland City with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (34)
"Very clean and a great location. The kitchen was well stocked with everything you needed to prepare meals. The furniture was comfortable and the tv looked brand new."
Chestnut Street Retreat

Cozy Bungalow in a nice friendly neighborhood

10.0 out of 10, Exceptional, (62)
"Everything was great can’t wait to stay again. "
Cozy Bungalow in a nice friendly neighborhood

Another Oasis just 6 miles from Holiday World

8.8 out of 10, Excellent, (10)
"This house was amazing! The house was way bigger then we could of imagined. My whole family came and everyone had their own space. The bedrooms and closets are huge. The best part was the outside area. The host was gracious and quick to help with any issue. We will definitely be back. "
Another Oasis just 6 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, (2)
"Visiting family for Easter, the property was exactly what we needed. Clean and quiet. "
The price is AED 433
AED 1,004 total
includes taxes & fees
30 Apr - 1 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.

2.0 star property
9.6 out of 10, Exceptional, (9)
"We stayed for a long weekend to visit family in Evansville. The place was exactly as described in the listing. Beds were comfortable. Fridge is really cold! Wifi worked great. The neighborhood is a mix of cute little well maintained bungalows, with some that could use some TLC. Good location with easy assess to Diamond. Will definitely stay again!"
The price is AED 202
AED 676 total
includes taxes & fees
30 Apr - 1 May
Vibrant and art-filled retreat, perfect for families and small groups.

Tranquil Hideaway: Your Private Lakefront Retreat

7.4 out of 10, Good, (3)
"This was a very beautiful lake house, it’s a nice place to find peaceful vibes and a wonderful view !!! I enjoyed myself very much so and wish I would have stayed one more day !! "
The price is AED 426
AED 901 total
includes taxes & fees
25 May - 26 May
Tranquil Hideaway: Your Private Lakefront Retreat

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

10.0 out of 10, Exceptional, (10)
"The space was very clean and inviting. We will stay here again if we are in the area. The rock path to get down to the basement area may be difficult for some people, but the host did say they are working on replacing that. We did meet the host as we were leaving and they were very kind and easy to hold a conversation with. When we arrived, the fireplace in the livingroom was going and there were lamps on throughout the space to make the home inviting and easy to navigate. This vrbo was...
The price is AED 489
AED 778 total
includes taxes & fees
30 Apr - 1 May
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

9.8 out of 10, Exceptional, (28)
"Needed a place to stay while we visited our parents nearby. Easy in and out. Only comment would be: it was nice to have coffee. QUALITY of coffee was kinda meh. At least it had caffeine "
The price is AED 375
AED 1,070 total
includes taxes & fees
8 May - 9 May
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

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

10.0 out of 10, Exceptional, (12)
"The house was as pictured, and had everything as listed. It was very clean! We had my husband's parents with us for this 8 night stay, and it was a good place to unwind and relax with our very busy week. We also traveled with our dog, and the fenced in yard was great for him! It is very close to the airport, and we did hear planes, but it was quiet in the house. Very nice neighborhood that my mother in law enjoyed walking in. My father in law enjoyed sitting in the gazebo with his coffee, and I...
Cozy Cottage, 3 mins from EVV, fenced yard

Stylish 3-bedroom home centrally located in wonderful Evansville

10.0 out of 10, Exceptional, (5)
"The cute house on Tennessee was the perfect place for my family and me to crash after a day of helping my sister move out of her house. We appreciated being able to relax after long days of packing and cleaning. "
Stylish 3-bedroom home centrally located in wonderful Evansville

Sweet Spot in the City

9.8 out of 10, Exceptional, (6)
"We had an amazing stay! This is the cuttest house. It's modern and clean. The location is perfect. We were able to walk to resturaunts and shops. Would love to go back! Definitely recommend!"
Sweet Spot in the City

Cozy 3BR Spacious home w/Patio -Sleeps8

10.0 out of 10, Exceptional, (2)
"Everything in the house was very nice. The owners were very accommodating in letting us have a later check out due to our fight departure change. The beds in all the rooms were very comfortable. The only thing missing was a full size mirror. I highly recommend this rental.. "
Cozy 3BR Spacious home w/Patio -Sleeps8

Barn in the Burgh

10.0 out of 10, Exceptional, (3)
"Spent the weekend for a retirement party. Home was amazing and would highly recommend "
The price is AED 393
AED 1,193 total
includes taxes & fees
29 Apr - 30 Apr
Barn in the Burgh

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

10.0 out of 10, Exceptional, (14)
"House was clean had everything we needed. Neighborhood was quiet and relaxing. Perfect weekend getaway "
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!

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

10.0 out of 10, Exceptional, (160)
"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

6.2 out of 10, (10)
"Jason has a nice cozy home. "
The price is AED 459
AED 980 total
includes taxes & fees
18 May - 19 May
Mid-Century Brick Bungalow Home

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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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.