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Holiday homes in Oak Park You’ll Love

Top-Rated Oak Park Holiday homes for Every Budget and Style!

Looking for a holiday home in Oak Park (Illinois)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Oak Park.

We found 52 Holiday-homes in Oak Park and the surrounding area (within 20 miles)

Chi-Town Ultimate Hideout 1-2-3 in Berwyn, USA

Chi-Town Ultimate Hideout 1-2-3

Holiday home in Berwyn near Oak Park, Illinois , 3101 Grove Avenue
Chi-Town Ultimate Hideout 1-2-3 is located in Berwyn, just 9 miles from United Center and 10 miles from Union Station.

Very good 1 Reviews 8.0

from $365.00 Show details »

Heart of Historic Riverside Home in Riverside, USA

Heart of Historic Riverside Home

Holiday home in Riverside near Oak Park, Illinois , 386 Audubon Road
Heart of Historic Riverside Home offers accommodations in Riverside, 9.3 miles from United Center and 11 miles from Union Station.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $86.00 Show details »

Chic Chicago Retreat home in Chicago, USA

Chic Chicago Retreat home

Holiday home in Chicago near Oak Park, Illinois
Chic Chicago Retreat home offers accommodations in Chicago, 3.5 miles from United Center and 4.7 miles from Guaranteed Rate Field.
  • Parking

Fabulous 6 Reviews 8.7

from $224.58 Show details »

West Pilsen Hideaway in Chicago, USA

West Pilsen Hideaway

Holiday home in Chicago near Oak Park, Illinois , 2334 South Hoyne
West Pilsen Hideaway offers accommodations in Chicago, 3.8 miles from Union Station and 4.3 miles from Field Museum of Natural History.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $97.00 Show details »

Spacious 5-BR House near Transit w Parking in Chicago, USA

Spacious 5-BR House near Transit w Parki...

Holiday home in Chicago near Oak Park, Illinois , 1868 South Millard Avenue
Offering a garden, Spacious 5-BR House near Transit w Parking offers accommodations in Chicago.
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 17 Reviews 8.6

from $345.51 Show details »

Chi-Town Hideout #1-2-3 in Berwyn, USA

Chi-Town Hideout #1-2-3

Holiday home in Berwyn near Oak Park, Illinois , 1436 Wenonah Avenue
Chi-Town Hideout #1-2-3 is located in Berwyn, just 8.4 miles from United Center and 10 miles from Union Station.

no reviews

from $387.33 Show details »

Ultimate Stay with Gym an Game Room Broadview IL 4BR House in Broadview, USA

Ultimate Stay with Gym an Game Room Broa...

Holiday home in Broadview near Oak Park, Illinois , 2345 16th Avenue
Ultimate Stay with Gym an Game Room Broadview IL 4BR House is located in Broadview, just 13 miles from Willis Tower and 13 miles from DePaul Universit...
  • Pets allowed

no reviews

from $70.00 Show details »

Modern Pop Art Decor Grill Games Broadview IL 3 bdrm House in Broadview, USA

Modern Pop Art Decor Grill Games Broadvi...

Holiday home in Broadview near Oak Park, Illinois , 2324 South 22nd Avenue
Modern Pop Art Decor Grill Games Broadview IL 3 bdrm House offers accommodations in Broadview, 11 miles from United Center and 12 miles from Union Sta...
  • Parking
  • Pets allowed

No reviews yet 1 Reviews 1.0

from $303.79 Show details »

Westchester Retreat King bed in Westchester, USA

Westchester Retreat King bed

Holiday home in Westchester near Oak Park, Illinois , 1143 Suffolk Avenue
Westchester Retreat King bed is located in Westchester, just 13 miles from Union Station and 13 miles from Willis Tower.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $387.54 Show details »

Opulence in Oak Park in Oak Park, USA

Opulence in Oak Park

Holiday home in Oak Park, Illinois , 1028 South Humphrey Avenue
Opulence in Oak Park is located in Oak Park, just 7.3 miles from Union Station and 7.8 miles from Willis Tower.
  • Parking

no reviews

from $384.17 Show details »

Luxury Home w King Bed Game Room and Fire Pit 17 miles Downtown in Westchester, USA

Luxury Home w King Bed Game Room and Fir...

Holiday home in Westchester near Oak Park, Illinois , 624 Norfolk Ave, Westchester, IL 60154, USA
Luxury Home w King Bed Game Room and Fire Pit 17 miles Downtown offers accommodations in Westchester, 12 miles from Union Station and 13 miles from Wi...
  • Parking
  • Pets allowed

no reviews

from $51.00 Show details »

Charming Oak Park Retreat with Fenced Backyard! in Oak Park, USA

Charming Oak Park Retreat with Fenced Ba...

Holiday home in Oak Park, Illinois
Charming Oak Park Retreat with Fenced Backyard! offers accommodations in Oak Park, 7.5 miles from Union Station and 8.1 miles from Willis Tower.
  • Parking
  • Pets allowed

Good 5 Reviews 7.2

from $190.64 Show details »

5 Mi to Millennium Park Apartment with Fireplaces in Chicago, USA

5 Mi to Millennium Park Apartment with F...

Holiday home in Chicago near Oak Park, Illinois
5 Mi to Millennium Park Apartment with Fireplaces offers accommodations in Chicago, 2.3 miles from United Center and 4.7 miles from Union Station.
  • Parking

Exceptional 3 Reviews 9.7

from $244.58 Show details »

13 Mi to Dtwn Chicago Maywood Home with Fireplace in Maywood, USA

13 Mi to Dtwn Chicago Maywood Home with...

Holiday home in Maywood near Oak Park, Illinois
13 Mi to Dtwn Chicago Maywood Home with Fireplace offers accommodations in Maywood, 13 miles from Union Station and 13 miles from Willis Tower.
  • Parking
  • Bar

Exceptional 2 Reviews 10.0

from $260.20 Show details »

Luxe Urban Retreat Near United Center in Chicago, USA

Luxe Urban Retreat Near United Center

Holiday home in Chicago near Oak Park, Illinois , 2705 W Warren Blvd
Luxe Urban Retreat Near United Center offers accommodations in Chicago, 3.1 miles from Union Station and 3.7 miles from Millennium Station.
  • Pets allowed
  • Family rooms

no reviews

from $72.00 Show details »

4 Mi to Dtwn Chicago Modern Home with Outdoor Space in Chicago, USA

4 Mi to Dtwn Chicago Modern Home with Ou...

Holiday home in Chicago near Oak Park, Illinois
4 Mi to Dtwn Chicago Modern Home with Outdoor Space offers accommodations in Chicago, 2.6 miles from Union Station and 3.1 miles from CIBC Theatre.
  • Parking

no reviews

from $54.00 Show details »

Luxe Downtown Historic Victorian, Premiere Location! in Oak Park, USA

Luxe Downtown Historic Victorian, Premie...

Holiday home in Oak Park, Illinois , 235 South Oak Park Avenue #2
6.5 miles from United Center in Oak Park, Luxe Downtown Historic Victorian, Premiere Location! features accommodations with access to a hot tub.
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

Exceptional 2 Reviews 10.0

from $56.00 Show details »

Quiet Chicago Townhome Walk to Subway Stations in Chicago, USA

Quiet Chicago Townhome Walk to Subway St...

Holiday home in Chicago near Oak Park, Illinois
Quiet Chicago Townhome Walk to Subway Stations offers accommodations in Chicago, 7.3 miles from Water Tower Chicago and 7.3 miles from Willis Tower.
  • Parking

no reviews

from $65.00 Show details »

Spacious Row Home next Transit near Downtown w Parking in Chicago, USA

Spacious Row Home next Transit near Down...

Holiday home in Chicago near Oak Park, Illinois , 3133 West Fulton Street
Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2 miles from United Center and 4 miles from Union Station.
  • Parking
  • Pets allowed
  • Family rooms

Very good 20 Reviews 8.5

from $363.07 Show details »

The Chicago Retreat Just 10 mins from Chicago Bulls Arena in Chicago, USA

The Chicago Retreat Just 10 mins from Ch...

Holiday home in Chicago near Oak Park, Illinois , 545 North Wood Street
The Chicago Retreat Just 10 mins from Chicago Bulls Arena is located in Chicago, just a 17-minute walk from United Center and 2.6 miles from Union Sta...
  • Parking

Pleasant 3 Reviews 6.7

from $301.33 Show details »

Classic Oak Park Home, 11 Mi to Downtown Chicago! in Oak Park, USA

Classic Oak Park Home, 11 Mi to Downtown...

Holiday home in Oak Park, Illinois
Classic Oak Park Home, 11 Mi to Downtown Chicago! is located in Oak Park, just 7 miles from United Center and 10 miles from Lincoln Park Zoo.
  • Parking
  • Spa and wellness centre

Superb 5 Reviews 9.2

from $388.50 Show details »

Luxe 4BR with Hot Tub & Game Room in Chicago, USA

Luxe 4BR with Hot Tub & Game Room

Holiday home in Chicago near Oak Park, Illinois , 1654 West Ohio Street
Luxe 4BR with Hot Tub & Game Room offers accommodations in Chicago, 2.5 miles from Union Station and 2.6 miles from Shops at Northbridge.
  • Parking
  • Pets allowed

Fabulous 5 Reviews 9.0

from $328.00 Show details »

Spacious West Town Oasis with Parking! in Chicago, USA

Spacious West Town Oasis with Parking!

Holiday home in Chicago near Oak Park, Illinois , 1656 West Erie Street
Spacious West Town Oasis with Parking! is located in Chicago, just 1.1 miles from United Center and 2.5 miles from Union Station.
  • Parking
  • Pets allowed

no reviews

from $72.00 Show details »

Wright at Home in Oak Park, USA

Wright at Home

Holiday home in Oak Park, Illinois
Wright at Home offers accommodations in Oak Park, 10 miles from Union Station and 10 miles from Lincoln Park Zoo.
  • Parking

Exceptional 3 Reviews 10.0

from $90.00 Show details »

Cute and Cozy Chicago Modern Condo in Chicago, USA

Cute and Cozy Chicago Modern Condo

Holiday home in Chicago near Oak Park, Illinois , 1625 W Superior St 3F, Chicago, IL 60622, USA
Cute and Cozy Chicago Modern Condo is located in Chicago, just 2.4 miles from Water Tower Chicago and 2.5 miles from Chicago Museum of Contemporary Ar...

no reviews

from $281.33 Show details »

Number of Holiday homes in Oak Park 52
Number of guest ratings 416
Average price per night $250.00
Lowest price per night $51,00
Highest price per night $1.440,48

Top 10 Cheapest Holiday-homes in Oak Park

Discover the Cheapest Holiday-homes in Oak Park – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Oak Park

Check out the Most Booked Holiday-homes in Oak Park – Based on Guest Popularity.

Holiday homes in Oak Park (Illinois), comfortable and familiar

Staying in a holiday or vacation home in Oak Park can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Oak Park for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Oak Park should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com