10 Best Vacation Rentals in Oak Park - Holiday Lettings - Cabins

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30 Vacation rentals

11

Private room rental in Oak Park

Illinois / Oak Park

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Beautiful Oak Park, IL home of Earnest Hemingway and Frank Lloyd Wright. We boast beautiful homes, superb restaurants, shops and we are next door to Chicago a world class city!! Welcome to my home where you will find comfortable beds, refreshments, conversation an …see more

from $55 / night

$300 - $370 / week

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Responds fast!
avg. 2 hours 19 minutes

from $55 / night

9

Home rental in Oak Park

Illinois / Oak Park

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Car not necessary
  • Air conditioning
- Safe and quiet residential area by the Oak Park Arts District - Many art shops, two cafes, Italian restaurant and family-friendly activities all within walking distance. - Space is master bedroom on the 2nd floor - Free parking on premise - 15-20 mins Chicago Loop/Dow …see more

from $40 / night

$280 / week

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from $40 / night

(3) Very Good 

25

Home rental in Oak Park

Illinois / Oak Park

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Oak Park Duplex. This charming Oak Park Duplex offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicago or enjoying the historic beauty of Oak Park. The home has been divided into two units. The top two floors (Duplex) are the rental …see more

from $170 / night

$1,190 / week

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Responds fast!
avg. 1 hour 18 minutes

from $170 / night

4

Home rental in Oak Park

Illinois / Oak Park

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Air conditioning
When traveling and looking for an upscale location. Oak Park offer a great traveler great food, entertainment, relaxing environment. Safe and a wide array of guided tours, Frank Lloyd Widget homes is just the start. My condo has two room with king bed half bath master b …see more

from $445 / night

$3,115 / week

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from $445 / night

(1) Excellent 

14

Apartment rental in Oak Park

Illinois / Oak Park

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Come relax in OAK PARK (OP) after a long day of shopping on Michigan Avenue, sightseeing in Chicago, or family gatherings. Just 10 minutes from downtown Chicago, Oak Park, and our flat offers the best of both worlds at a price you can afford. Just blocks from 2 trai …see more

from $140 / night

$980 / week

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Responds fast!
avg. 1 hour 24 minutes

from $140 / night

(1) Excellent 

7

Oak Park Vacation home rental

Illinois / Oak Park

1 1 7 nights min

  • 1 bedroom
  • Sleeps 1
  • 7 nights min
  • Nearest beach 15 mi
  • Car not necessary
  • Private garden
Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities i …see more

from $25 / night

$175 / week

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from $25 / night

5

Vacation apartment in Oak Park

Illinois / Oak Park

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Eclectic Artists Flat Close2Chicago & Fitzgerald's Live Music Club Located near the Oak Park Arts District, this living space is located on the second floor of a brick home. The flat is colorful and filled with art with an eclectic ambiance. Very large rooms and spaci …see more

from $115 / night

$805 / week

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Responds fast!
avg. 1 hour 24 minutes

from $115 / night

7

Home rental in Oak Park

Illinois / Oak Park

1 1 7 nights min

  • 1 bedroom
  • Sleeps 1
  • 7 nights min
  • Nearest beach 15 mi
  • Car not necessary
  • Air conditioning
Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities i …see more

from $30 / night

$210 / week

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from $30 / night

7

Home rental in Oak Park

Illinois / Oak Park

4 1 7 nights min

  • 4 bedrooms
  • Sleeps 1
  • 7 nights min
  • Nearest beach 15 mi
  • Car not necessary
  • Air conditioning
Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities i …see more

from $43 / night

$300 / week

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from $43 / night

7

Oak Park Vacation home rental

Illinois / Oak Park

1 1 7 nights min

  • 1 bedroom
  • Sleeps 1
  • 7 nights min
  • Nearest beach 15 mi
  • Car not necessary
  • Private garden
Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities i …see more

from $25 / night

$175 / week

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from $25 / night

6

Oak Park Vacation home rental

Illinois / Oak Park

1 1 7 nights min

  • 1 bedroom
  • Sleeps 1
  • 7 nights min
  • Nearest beach 15 mi
  • Car not necessary
  • Private garden
Located just west of Chicago - Oak Park is a historic neighborhood 30 minutes from downtown. Humphrey Homestay provides a residence for international students or medical students completing rotations in the Chicagoland area. We provide home cooked meals, all utilities i …see more

from $30 / night

$210 / week

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from $30 / night