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

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, (6)
"We came in the night before our t-time and was the perfect place to relax with friends and get ready for a day of golf"
The price is AED 433
AED 716 total
includes taxes & fees
23 Sep - 24 Sep
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Historic Home by Dogwood Lake/Glendale
Dining
Historic Home by Dogwood Lake/Glendale
10.0 out of 10, Exceptional, (4)
"We liked that it was in the country. It was quiet and peaceful. It had all the modern amenities making our stay pleasant. They creatively merged the old and new part of the home. The only thing we would have checked before we booked was confirm the size of the bed. We are larger stature people and would have preferred a larger bed. Our host was communicative from the moment we booked through check in. All in all it was delightful . "
Historic Home by Dogwood Lake/Glendale
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, (23)
"Property was very quiet, rustic yet homey. Worked perfect for our family. Host was very accommodating and communicative."
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
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 AED 397
AED 883 total
includes taxes & fees
8 Oct - 9 Oct
Fenced-In Yard on the East Side
Mid-Century Brick Bungalow Home
Living area
Mid-Century Brick Bungalow Home
7.6 out of 10, Good, (4)
"The house was beautiful. I was there to celebrate Mothers Day with my oldest son and his wife. I brought my dog as a car companion and she really enjoyed the fenced in back yard. In fact, we spent 2 days in the shaded back yard with my son and his wife. The neighborhood was quiet and felt safe. I can see myself spending more time at this house for future visits."
The price is AED 404
AED 912 total
includes taxes & fees
22 Oct - 23 Oct
Mid-Century Brick Bungalow Home
Cozy Retreat minutes from Holiday World, Santa Claus IN, and Lincoln State Park
Memories On Medcalf
Cozy Retreat minutes from Holiday World, Santa Claus IN, and Lincoln State Park
2.0 star property
9.6 out of 10, Exceptional, (13)
"It was a cute place! Met all of our expectations and in a quiet town!"
Cozy Retreat minutes from Holiday World, Santa Claus IN, and Lincoln State Park
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, (12)
"Check in and check out was easy. Property was as described. "
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Comfort and Charm Highly Recommended
Summer time view of front of house.
Comfort and Charm Highly Recommended
9.4 out of 10, Exceptional, (10)
"Great place! It was spacious and clean. The host was accommodating and responded quickly to questions. We asked about a Keurig and there wasn't one on-site so the host brought one to us! There was already snacks and some food and water in the fridge so we didn't have to go out to make a food run immediately upon arrival. Kitchen was equipped with everything - cutlery, cooking utensils and pots, etc. Basic spices, coffee, etc. Plenty of blankets and pillows... very spacious. Great location. Just...
Comfort and Charm Highly Recommended
Pet friendly home in Evansville
Living area
Pet friendly home in Evansville
10.0 out of 10, Exceptional, (11)
"Was happy to find a place to stay while visiting Evansville. Will use again. Spacious rooms. "
Pet friendly home in Evansville
Great new home - just for you!
Exterior
Great new home - just for you!
9.8 out of 10, Exceptional, (29)
"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, (32)
"We came into town for the Red, White, and Brauen concert and booked this house to stay in. It was perfect for our needs. It was like going to grandma’s house! It was very clean, in a nice quiet neighborhood, and had comfortable beds. All we really used the property for was sleeping and bathing (always had plenty of hot water). "
Chestnut Street Retreat
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 AED 422
AED 676 total
includes taxes & fees
30 Sep - 1 Oct
Comfortable house where guests feel welcome. 10 minutes from Evansville Airport
Your home away from home.
Exterior
Your home away from home.
Your home away from home.
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
Cozy Bungalow in a nice friendly neighborhood
Cozy Bungalow in a nice friendly neighborhood
10.0 out of 10, Exceptional, (54)
"There was a bit of a snafu when we were first checking in, but the hosts handled it promptly and efficiently. Quiet and comfortable, perfect for our getaway. Bath and Body Works toiletries were a nice touch!!!"
Cozy Bungalow in a nice friendly neighborhood
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)
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
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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.
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Other property types in Oakland City

Guest House with acreage to explore.
Interior
Guest House with acreage to explore.
9.6 out of 10, Exceptional, (44)
"This place not only met expectations but exceeded them. The place was super clean and very homey. The host has very nice trail as well as a amazing fishing pond. Take full advantage of this location and too notch host "
The price is AED 459
AED 597 total
includes taxes & fees
23 Sep - 24 Sep
Guest House with acreage to explore.
Mid-Century Brick Bungalow Home
Living area
Mid-Century Brick Bungalow Home
7.6 out of 10, Good, (4)
"The house was beautiful. I was there to celebrate Mothers Day with my oldest son and his wife. I brought my dog as a car companion and she really enjoyed the fenced in back yard. In fact, we spent 2 days in the shaded back yard with my son and his wife. The neighborhood was quiet and felt safe. I can see myself spending more time at this house for future visits."
The price is AED 404
AED 912 total
includes taxes & fees
22 Oct - 23 Oct
Mid-Century Brick Bungalow Home
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, (6)
"We came in the night before our t-time and was the perfect place to relax with friends and get ready for a day of golf"
The price is AED 433
AED 716 total
includes taxes & fees
23 Sep - 24 Sep
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
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.