Vacation rentals in Oakland City

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Top-rated vacation rentals in Oakland City

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Cabin in Winslow

4.9 out of 5 average rating, 251 reviews

Primitive Historical Escape with Modern Amenities

If you desire an escape from the bigger city life and want to slow things down a bit with a place that makes you feel like you have went back in time to a simpler time, while still being close to it all, then this cabin getaway is your destination. Our cabin is perfect for a family weekend retreat, anniversary celebrations, and hunters. We are excited to be able to continue to maintain this historical building and still be able to offer it as a place for people to enjoy and stay in to this day.

Nov 10 – 17

R2,925 ZAR per night
Guest favorite

Home in Winslow

5.0 out of 5 average rating, 16 reviews

Twin Lakes

Twin Lakes has a unique location on 60 acres in between 2 wildlife filled lakes stock with fish and wild geese flying in and out. A habitat for deer, squires and rabbits. The house is located down a long drive off the county road in a rural area. Very peaceful to sit on the back deck in the morning and enjoy a cup of coffee and watch the wildlife. Fishermen are invited to enjoy the lake from lakeside or small boat. The home is very comfortable with 2 queen size beds and a futon. Enjoy & relax!

Dec 7 – 14

R2,708 ZAR per night
Guest favorite

Loft in Huntingburg

4.92 out of 5 average rating, 119 reviews

Lovely Country Loft Lake, Hiking, Woods, Relaxing

Take it easy at this unique and tranquil getaway. This loft was made from wood sawn and milled on this farm. Enjoy Indiana hardwoods as they surround you in this space. Centrally located, you are not far from Holiday World, Jasper, Lincoln City, Patoka Lake and Historic Huntingburg. The Master Bedroom boasts a king-size bed. The living area has two twin beds, TV, WiFi and Kitchen. This space is perfect for singles, couples, or small families. Most love the spiral staircase and large deck.

Mar 12 – 19

R1,641 ZAR per night

Popular amenities for Oakland City vacation rentals

Other great vacation rentals in Oakland City

Guest favorite

Home in Vincennes

4.96 out of 5 average rating, 73 reviews

Cheerful 3-bedroom home with huge yard

Aug 7 – 14

R2,367 ZAR per night
Guest favorite

Home in Vincennes

5.0 out of 5 average rating, 30 reviews

Ernie's Place

Nov 18 – 25

R2,348 ZAR per night
Guest favorite

Home in Haubstadt

4.99 out of 5 average rating, 67 reviews

Small town charm

Jan 26 – Feb 2

R1,585 ZAR per night
Guest favorite

Home in Vincennes

4.94 out of 5 average rating, 66 reviews

Cozy Two Bedroom Home

Jul 25 – Aug 1

R1,618 ZAR per night
Guest favorite

Cabin in Fairfield

4.97 out of 5 average rating, 69 reviews

Forested Retreat

Aug 11 – 18

R1,991 ZAR per night
Guest favorite

Home in Owensville

4.95 out of 5 average rating, 59 reviews

New Luxurious Modern Private Home Near Evansville

Mar 15 – 22

R4,147 ZAR per night
Superhost

Loft in Washington

4.86 out of 5 average rating, 72 reviews

Lovely 3 bedroom loft apartment!

Aug 23 – 30

R2,565 ZAR per night
Guest favorite

Home in Olney

4.96 out of 5 average rating, 25 reviews

Lakeside Lodge with Private Dock and Kids' Kayaks

Aug 13 – 20

R2,860 ZAR per night
Guest favorite

Home in Huntingburg

5.0 out of 5 average rating, 88 reviews

Chestnut Street Retreat

Nov 25 – Dec 2

R2,728 ZAR per night
Guest favorite

Home in Jasper

5.0 out of 5 average rating, 26 reviews

Lake House

May 21 – 28

R6,260 ZAR per night
Guest favorite

Home in Loogootee

4.86 out of 5 average rating, 64 reviews

The Getaway House

May 28 – Jun 4

R1,136 ZAR per night
Guest favorite

Cabin in West Salem

4.99 out of 5 average rating, 99 reviews

Lake Cabin in the Woods

Oct 27 – Nov 3

R2,893 ZAR per night

Destinations to explore

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  4. Gibson County
  5. Oakland City