Default HTG hotel image

Oakland City Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Oakland City vacation rentals

Exterior

1. 3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Ferdinand
10.0 out of 10, Exceptional, (3 reviews)
"Very cozy and clean place! It was perfect for our group of five, including three teenagers, while we visited Holiday World. Shane is a wonderful host, and the thoughtful touches - like the selection of snacks - made us feel especially welcome. Communication was easy throughout our stay. I was also fascinated by the historical books displayed on the shelves - they were such a unique and memorable touch, adding to a very historic feel of the place and the town. "
United States
Svitlana T.
The price is AED 878
AED 1,362 total
includes taxes & fees
2 Sep - 3 Sep
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
3 bedrooms, WiFi, bed sheets

2. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
The price is AED 1,125
AED 1,803 total
includes taxes & fees
1 Sep - 2 Sep
Run Away Reindeer Retreat
Smart TV

3. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (11 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
The price is AED 1,194
AED 1,530 total
includes taxes & fees
8 Sep - 9 Sep
Family Friendly Lakehouse with great views!
Interior

4. Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Huntingburg
9.8 out of 10, Exceptional, (28 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is AED 364
AED 724 total
includes taxes & fees
1 Sep - 2 Sep
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Coffee/tea maker, fridge, microwave, oven

5. 5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.8 out of 10, Exceptional, (33 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is AED 1,102
AED 1,761 total
includes taxes & fees
1 Oct - 2 Oct
5 Miles from Holiday World sleeps 11+ —Family Escape
House (2 Bedrooms) | Interior

6. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
3.0 star property
Gentryville
The price is AED 507
AED 1,398 total
includes taxes & fees
2 Sep - 3 Sep
The Cowboys Slumber' 2 Mi to Lincoln State Park
TV

7. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (1 review)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
The price is AED 364
AED 1,436 total
includes taxes & fees
2 Sep - 3 Sep
The Cowboys Slumber' 2 Mi to Lincoln State Park
TV

8. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.6 out of 10, Excellent, (28 reviews)
"Cute little cabin, fun for kids. "
United States
Paul S.
The price is AED 643
AED 1,090 total
includes taxes & fees
1 Sep - 2 Sep
Yellow Banks Log Cabin with Lake Views
Exterior

9. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.8 out of 10, Exceptional, (8 reviews)
"This was a quiet, clean, and convenient little cabin close to Holiday World which is what we stayed for. "
United States
Ashley J.
The price is AED 569
AED 1,037 total
includes taxes & fees
1 Sep - 2 Sep
Yellow Banks Log Cabin With Waterfront Views
Property grounds

10. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.2 out of 10, Wonderful, (24 reviews)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is AED 551
AED 1,012 total
includes taxes & fees
1 Sep - 2 Sep
Yellow Banks Log Cabin With Waterfront Views
Outdoor dining

11. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.0 out of 10, Wonderful, (17 reviews)
"Excellent cabins! We had so much fun!!!"
United States
Leslie H.
The price is AED 551
AED 1,012 total
includes taxes & fees
1 Sep - 2 Sep
Yellow Banks Log Cabin With Waterfront Views
Smart TV

12. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (73 reviews)
"The place was great, quiet and peaceful! "
United States
brian k.
The price is AED 525
AED 675 total
includes taxes & fees
1 Sep - 2 Sep
Guest House with acreage to explore.
Outdoor dining

13. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.4 out of 10, Exceptional, (33 reviews)
"We had a great time and enjoyed our stay!"
United States
Anonymous traveler
The price is AED 459
AED 893 total
includes taxes & fees
1 Sep - 2 Sep
Yellow Banks Log Cabin With Waterfront Views
Exterior

14. THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Lynnville
9.8 out of 10, Exceptional, (16 reviews)
"Very attentive host. Good value. This house was perfect for our group's trip to Holiday World. We're looking at staying again in the future."
United States
Patricia G.
The price is AED 584
AED 1,135 total
includes taxes & fees
27 Sep - 28 Sep
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Coffee/tea maker, fridge, microwave, oven

15. Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed the stay immensely. Very clean. Will stay again. "
United States
Mary P.
The price is AED 444
AED 1,529 total
includes taxes & fees
8 Sep - 9 Sep
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Private kitchen

16. RiverStone Retreat C

RiverStone Retreat C
Newburgh
10.0 out of 10, Exceptional, (1 review)
"This property is beautiful. The hosts are so kind. We’ll be back!"
United States
David
The price is AED 340
AED 788 total
includes taxes & fees
1 Sep - 2 Sep
RiverStone Retreat C
Smart TV, books

17. Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.6 out of 10, Exceptional, (43 reviews)
"We have absolutely loved it here the wildlife the owners are amazing. I hope that next time we’re in town will be able to stay here again."
United States
Kristen J.
The price is AED 337
AED 1,019 total
includes taxes & fees
1 Sep - 2 Sep
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Fridge, microwave, oven, stovetop

18. RiverStone Retreat D

RiverStone Retreat D
Newburgh
9.0 out of 10, Wonderful, (2 reviews)
"Toilet moves when you sit on it, needs fixed!Good cooling and A/C!Need more towels ahead of time (face, hand and bath sizes) without having to ask after checking in. I listed 3 guests and did not have enough for 1 guest and the length of stay. Once should not have to request the minimum needed.Thank you for providing them once requested however!"
United States
jim a.
RiverStone Retreat D
Private kitchen

19. RiverStone Retreat B

RiverStone Retreat B
Newburgh
The price is AED 312
AED 646 total
includes taxes & fees
6 Sep - 7 Sep
RiverStone Retreat B
Living area

20. Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland City Hotel Reviews

Baymont by Wyndham Washington

Baymont by Wyndham Washington

8/10 Good
"Staff always very pleasant and friendly."
Debbie 1-night trip
Posted 12 hours ago
Baymont by Wyndham Washington

Frequently asked questions

Can I find a vacation rental in Oakland City?

Yes, you can find vacation rentals close to well known sights in Oakland City, or you can go with a more remote option if you're looking for relaxation. Oakland City is known for its restaurants and university setting.

What are some of the best vacation rentals that Oakland City has to offer?

Run Away Reindeer Retreat: This vacation home rental near Oakland City offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

What can I see and do in Oakland City?

Visit the sights such as Oakland City University while you're exploring the area.

What are vacation rentals like in Oakland City?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Oakland City. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for families.