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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 53 Vacation Homes in Oakland City with updated reviews, rates, and availability.

BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities
Outdoor dining

BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities

10.0 out of 10, Exceptional, (4)
"Bobby’s place was perfect for our family stay in Evansville. The location was convenient and the house was exactly as described - clean and comfortable. Would def stay here again!"
BRAND NEW: Oakside Retreat with MASSIVE Yard & High End Amenities
Charming 2-bedroom lake house in Dale
Living area

Charming 2-bedroom lake house in Dale

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 356
AED 831 total
includes taxes & fees
24 Feb - 25 Feb
Charming 2-bedroom lake house in Dale
Fenced-In Yard on the East Side
Living area

Fenced-In Yard on the East Side

10.0 out of 10, Exceptional, (8)
"Overall the house was very nice and in a great spot for the concert we attended."
The price is AED 551
AED 1,081 total
includes taxes & fees
26 Feb - 27 Feb
Fenced-In Yard on the East Side
Cozy Cottage, 3 mins from EVV, fenced yard
Miscellaneous

Cozy Cottage, 3 mins from EVV, fenced yard

10.0 out of 10, Exceptional, (9)
"We were just in for a quick weekend stay. The house was perfect for us and very clean. Host is very punctual for communication and was very accommodating for us! The yard was wonderful for our pups. Clean up bags were also provided which was perfect since we forgot ours. The pups enjoyed running all over the yard tiring themselves out for the evening! There is a fire pit that we definitely would have used had we stayed longer. A place we would highly recommend if headed to the Evansville area! "
Cozy Cottage, 3 mins from EVV, fenced yard
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Large front porch to sit and enjoy the neighborhood.

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, (1)
"“The Getaway” was a good location to travel to other areas & see different things. The home was well stocked with everything you would need. Aubrey answered all questions and responded quickly. She even gave us some nearby things to do. "
The price is AED 621
AED 1,148 total
includes taxes & fees
19 Mar - 20 Mar
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.
Living area

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

2.0 star property
9.2 out of 10, Wonderful, (5)
"Enjoyed the house. Had friends for dinner one night and family the next fay for our hilday get together. The house is cute, clean and had everything we needed. Tge host was readily available when we had questions. I would definitely stay again!"
Vibrant and art-filled retreat, perfect for families and small groups.
Enchanting historical home with River View
Living area

Enchanting historical home with River View

9.8 out of 10, Exceptional, (17)
"This home was on a very quiet street. The interior has been beautifully updated. The beds were, for the most part, comfortable. Plenty of blankets and pillows were provided. The kitchen was stocked very well for our needs. The owner reponded with any questions I had very promptly and check out was so easy! We were in town for softball so we were in and out of the house often and there was plenty of room for 3 adults and 4 kids (including an infant). Really enjoyed the comfort of this home!"
The price is AED 514
AED 1,222 total
includes taxes & fees
23 Feb - 24 Feb
Enchanting historical home with River View
Nature’s Retreat with Game Room | Hot Tub | Sauna

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

2.0 star property
Nature’s Retreat with Game Room | Hot Tub | Sauna
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Exterior

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 Family Oasis just 6 miles from Holiday World
House

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
Barn in the Burgh
Exterior

Barn in the Burgh

10.0 out of 10, Exceptional, (1)
"Hosted a small Sweet 16 birthday for our daughter here for her and 6 of her friends. Great place to decorate, dance and have fun along with a great area for them to have a sleepover while mom and dad relaxed in the main part of the barn. We are from the area but would certainly rent again for family get togethers or small events. Everyone loved the cornhole boards and ping pong table... loved that they provide table and chairs that can be set up as needed too. "
The price is AED 647
AED 1,506 total
includes taxes & fees
11 Mar - 12 Mar
Barn in the Burgh
River View in Downtown Newburgh
Property grounds

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
Cozy Bungalow in a nice friendly neighborhood

Cozy Bungalow in a nice friendly neighborhood

9.8 out of 10, Exceptional, (59)
"My husband and I stayed in the Bungalow for a month. Kevin was very pleasant. When severe weather hit he was helpful in making sure we had ice melt and checked on our other needs. The house is very comfortable. The kitchen is fully equipped. My only suggested improvements would be to have another reading lamp in the living room and blinds on the kitchen door and window. We highly recommend this house."
Cozy Bungalow in a nice friendly neighborhood
X Marks the Spot(Blue)1.5 miles from Holiday World
Large kitchen with dishwasher

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

9.8 out of 10, Exceptional, (8)
"We stayed here to spend two full days at Holiday World with our families. There were 5 adults and 4 kids. There were plenty of kitchen items for cooking. Excellent space for that post-park resting to be up and ready for the next day! Will definitely stay again! "
X Marks the Spot(Blue)1.5 miles from Holiday World
Mid-Century Brick Bungalow Home
Living area

Mid-Century Brick Bungalow Home

6.4 out of 10, (9)
"Jason has a nice cozy home. "
The price is AED 441
AED 950 total
includes taxes & fees
2 Mar - 3 Mar
Mid-Century Brick Bungalow Home
Comfortable house where guests feel welcome. 10 minutes from Evansville Airport
Exterior

Comfortable house where guests feel welcome. 10 minutes from Evansville Airport

6.0 out of 10, (2)
"Our stay at the house was absolutely incredible. The location, amenities, and hospitality were top-notch. The place was spotless and beautifully decorated, with every detail carefully thought out. The kitchen was fully equipped, and the house is located in a safe area. The host was incredibly welcoming and provided us with all the information we needed for a smooth check-in. They even left a welcome basket for us, which was a lovely touch."
Comfortable house where guests feel welcome. 10 minutes from Evansville Airport
X Marks the Spot (Purple)
Welcome!!!

X Marks the Spot (Purple)

10.0 out of 10, Exceptional, (8)
"We stayed here while spending the weekend at Holiday World. It is very clean and comfortable with plenty of space for the kids to run around. After a long day in the park it’s the perfect spot to go back to."
X Marks the Spot (Purple)
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Property grounds

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

10.0 out of 10, Exceptional, (8)
"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
24 Feb - 25 Feb
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Another Oasis just 6 miles from Holiday World
Outdoor area with corn hole boards, fire pit and children's tree swing

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
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Living area

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

9.8 out of 10, Exceptional, (27)
"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
24 Feb - 25 Feb
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
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

< 1 Mi to Oakland City University: Quiet Studio
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< 1 Mi to Oakland City University: Quiet Studio

< 1 Mi to Oakland City University: Quiet Studio
Golf Course Views: Oakland City Retreat
Oakland City Vacation Rental | 3BR | 2BA | Step-Free Access | 1,750 Sq Ft

Golf Course Views: Oakland City Retreat

Golf Course Views: Oakland City Retreat
Walk to OCU, Golf: Updated Oakland City Studio!
Oakland City Vacation Rental | Studio | 1BA | 450 Sq Ft | Step-Free Entry

Walk to OCU, Golf: Updated Oakland City Studio!

Walk to OCU, Golf: Updated Oakland City Studio!
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.