Oak Park vacation rentals

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Best Oak Park vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$0 - $584$584 - $1,168$1,168 - $1,752$1,752 - $2,335$2,335+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Oak Park

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Cozy, Comfortable And Convenient Apartment. Close To Everything! - Oak Park - Kitchen
Cozy, Comfortable And Convenient Apartment. Close To Everything!
Oak Park, IL
Free Wi-Fi
$311+
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1br Apartment - Walk To Shops - Downtown Oak Park - Oak Park - Kitchen
1br Apartment - Walk To Shops - Downtown Oak Park
Oak Park, IL
$210+
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Peaceful Beauty in Historic District - Walkable - Winter Month Stay Special - Oak Park - Living room
Peaceful Beauty in Historic District - Walkable - Winter Month Stay Special
Oak Park, IL
9.7Wonderful(33)
Free Wi-Fi
Pool
$272+
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Beautiful Cozy Apartment - Oak Park - Living room
Beautiful Cozy Apartment
Oak Park, IL
6.6Okay(3)
$195+
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Sunny Jumbo Studio in the Heart of Oak Park - Oak Park - Patio
Sunny Jumbo Studio in the Heart of Oak Park
Oak Park, IL
$184+
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Modern Vibes 1br/1ba Oak Park IL - Oak Park - Balcony
Modern Vibes 1br/1ba Oak Park IL
Oak Park, IL
7.6Good(10)
$267+
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8 Mi to Chicago Oak Park Home with Fenced Backyard! - Oak Park - Living room
8 Mi to Chicago Oak Park Home with Fenced Backyard!
Oak Park, IL
7.7Good(2)
Free Wi-Fi
Pet friendly
$207+
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A quiet stay while you are away - Oak Park - Living room
A quiet stay while you are away
Oak Park, IL
Free Wi-Fi
$279+
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Chic Suite/Mins to L Train /Laundry/Free Parking - Oak Park - Living room
Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park, IL
Free Wi-Fi
$210+
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Oak Park, IL, entire house, short walk to train. - Oak Park - Living room
Oak Park, IL, entire house, short walk to train.
Oak Park, IL
9.2Wonderful(15)
Free Wi-Fi
$369+
Check availability
Historic Oak Park Home for 6 / Hemingway District - Oak Park - Bedroom
Historic Oak Park Home for 6 / Hemingway District
Oak Park, IL
9.2Wonderful(31)
Parking
Free Wi-Fi
$372+
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Cozy1 Bdrm Apartment Located In The Hear - Oak Park - Restaurant
Cozy1 Bdrm Apartment Located In The Hear
Oak Park, IL
8.5Very good(9)
$209+
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Lovely vintage Oak Park 3bd 1ba perfectly located near public transit & Chicago - Oak Park - Dining room
Lovely vintage Oak Park 3bd 1ba perfectly located near public transit & Chicago
Oak Park, IL
8.7Very good(11)
Parking
Free Wi-Fi
$317+
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Charming Chicago-Style, Vintage, Tv Nfl Pass - Oak Park - Living room
Charming Chicago-Style, Vintage, Tv Nfl Pass
Oak Park, IL
$138+
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Homestay - Oak Park Arts District Homestay - Oak Park
Homestay - Oak Park Arts District Homestay
Oak Park, IL
$76+
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Oak Park Downtown King Bed Rooftop Fitness Center Top Flr City View - Oak Park
Oak Park Downtown King Bed Rooftop Fitness Center Top Flr City View
Oak Park, IL
8.7Very good(7)
Free Wi-Fi
Pet friendly
$448+
Check availability
Useful Info

Good to know

Low season

April

High season

October

Average price (weeknight)

$195

Average price (weekend night)

$277
Cheapest month to stay with an average 54% drop in price.
Most expensive month to stay with an average 98% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Oak Park vacation rental deals

  • Vacation rentals in Oak Park are around 46% more expensive than hotels on average. Search here to compare prices for all accommodation types in Oak Park.
  • The best vacation rental properties in Oak Park are Peaceful Beauty in Historic District - Walkable - Winter Month Stay Special (9.7, 33 reviews), Historic Oak Park Home for 6 / Hemingway District (9.2, 31) and Historic Oak Park Home for 6 / Hemingway District (9.2, 31), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Oak Park, you should consider visiting during the low season. The cheapest vacation homes in Oak Park can be found in April and February.
  • The cheapest night for renting a vacation home in Oak Park is Sunday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Oak Park for 21 days.

FAQs when booking a vacation home in Oak Park

  • How much is a vacation rental for a week in Oak Park?

    The average price for a weekly Oak Park vacation rental found by KAYAK users in the last 2 weeks is $1,618.

  • How much is a vacation rental for a month in Oak Park?

    The average price for a monthly Oak Park vacation rental found by KAYAK users in the last 2 weeks is $6,932.

  • What types of vacation rentals are available in Oak Park?

    There are loads of different property types that you can make your vacation home in Oak Park. You’ll find apartments, condos, houses and homestays.

  • Are there any pet-friendly vacation rentals in Oak Park?

    There are a number of dog and pet-friendly Oak Park vacation rentals, with around 15% allowing you to bring your pet along with you.

  • How much is a vacation rental in Oak Park for tonight?

    In the last 72 hours, users have found Oak Park vacation rentals for tonight for as low as $226. Search here for similar prices

  • How can I find vacation rentals near me in Oak Park?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Oak Park?

Our map will help you find the perfect place to stay in Oak Park by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Oak Park

Oak Park vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Oak Park. Find cheap vacation homes to rent in Oak Park. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Oak Park that suits you best.

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