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Compare 42 Vacation Homes in Oakland City with updated reviews, rates, and availability.

Cozy Bungalow in a nice friendly neighborhood

Cozy Bungalow in a nice friendly neighborhood

9.8 out of 10, Exceptional, (57)
"I rented this great bungalow for my son and Grandson, who had a hockey weekend. They loved the house, and it was very convenient to get to the ice rinks, and other attractions in Evansville. My son said the beds were really comfy! "
Cozy Bungalow in a nice friendly neighborhood
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 SAR 499
SAR 803 total
includes taxes & fees
24 Nov - 25 Nov
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Comfort and Charm Highly Recommended
Summer time view of front of house.

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
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8, Lg Drive, WiFi, Tankless Water Htr
Large front porch to sit and enjoy the neighborhood.

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

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 SAR 597
SAR 1,123 total
includes taxes & fees
1 Dec - 2 Dec
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8, Lg Drive, WiFi, Tankless Water Htr
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, (24)
"Great house. Everything you will need for your stay. Owners are super nice. Turkeys and deer in the yard in the evening. I will try to stay here anytime i'm in that area."
The price is SAR 383
SAR 1,093 total
includes taxes & fees
4 Dec - 5 Dec
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
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."
The price is SAR 413
SAR 669 total
includes taxes & fees
24 Nov - 25 Nov
Comfortable house where guests feel welcome. 10 minutes from Evansville Airport
Charming 2-bedroom pet-friendly duplex in fabulous Newburgh with Hot Tub
Living area

Charming 2-bedroom pet-friendly duplex in fabulous Newburgh with Hot Tub

Charming 2-bedroom pet-friendly duplex in fabulous Newburgh with Hot Tub
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
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
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
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)
Fenced-In Yard on the East Side
Living area

Fenced-In Yard on the East Side

10.0 out of 10, Exceptional, (6)
"After a long hot day at the car show, it was nice to cal it a day in the clean, cool & comfortable cottage we would call home for our time in Evansville. "
The price is SAR 563
SAR 1,097 total
includes taxes & fees
4 Dec - 5 Dec
Fenced-In Yard on the East Side
X Marks the Spot (Green)
Welcome!!

X Marks the Spot (Green)

9.6 out of 10, Exceptional, (4)
"We had a great visit and will rent here again, close to Holiday World (across the street) great for families - teens and littles had a great time. "
X Marks the Spot (Green)
X Marks the Spot(Yellow)1.5 mi. from Holiday World
Full size bed

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

9.8 out of 10, Exceptional, (11)
"Had everything we needed. Especially enjoyed the front porch and fire pit. Nice big yard for grandkids to play when not at the park. Great spot! Thanks!"
X Marks the Spot(Yellow)1.5 mi. from Holiday World
Mid-Century Brick Bungalow Home
Living area

Mid-Century Brick Bungalow Home

6.0 out of 10, (8)
"good for a night was taken good care of just needed the yard mowed"
The price is SAR 282
SAR 756 total
includes taxes & fees
4 Dec - 5 Dec
Mid-Century Brick Bungalow Home
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 SAR 526
SAR 1,257 total
includes taxes & fees
25 Nov - 26 Nov
Enchanting historical home with River View
Great new home - just for you!
Exterior

Great new home - just for you!

9.8 out of 10, Exceptional, (30)
"We were very comfortable felt like we were at home"
Great new home - just for you!
Chestnut Street Retreat
Exterior

Chestnut Street Retreat

10.0 out of 10, Exceptional, (33)
"My family and I came down for Holiday World. Perfect homey place to relax before and after! Would totally return!"
Chestnut Street Retreat
Newburgh Newsie - 3BR, 2.5BA, Gym, Patio, New Construction in Amazing Location!
Exterior

Newburgh Newsie - 3BR, 2.5BA, Gym, Patio, New Construction in Amazing Location!

Newburgh Newsie - 3BR, 2.5BA, Gym, Patio, New Construction in Amazing Location!
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

Guest House with acreage to explore.
Living area

Guest House with acreage to explore.

9.6 out of 10, Exceptional, (46)
"Place was as described and perfect for us. Clean, comfortable and host was great with communication. Between the two of us we caught over 30 fish in the pond. Very fun. Thank you for a great stay "
The price is SAR 469
SAR 610 total
includes taxes & fees
25 Nov - 26 Nov
Guest House with acreage to explore.
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
8.0 out of 10, Very Good, (1)
"Nice clean stay for a quick weekend and close to downtown. "
Vibrant and art-filled retreat, perfect for families and small groups.
Yellow Banks Log Cabin with Lake Views
Front view

Yellow Banks Log Cabin with Lake Views

9.2 out of 10, Wonderful, (11)
"Nice secluded area, very tranquil setting "
The price is SAR 563
SAR 1,030 total
includes taxes & fees
24 Nov - 25 Nov
Yellow Banks Log Cabin with Lake Views
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.