182+ Vacation Rentals & Holiday Homes in Oak Park |
  1. USA
  2. Illinois
  3. Chicago
  4. Oak Park

Oak Park Accommodations - Hotels & Rentals

About Oak Park Vacation Rentals

Discover More than 182 Incredible Getaway Rentals Available in Oak Park. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Oak Park.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Oak Park, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Oak Park. The Average Size of Places to Stay Near Oak Park is 890.86 ft², with Prices Averaging US $294 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Oak Park. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

Show more
Show less

Top Hotels & Vacation Rentals in Oak Park

Type Count
Holiday Apartments 116
Vacation Homes 57

Use these Quick Filters to Find a Vacation Rental in Oak Park

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Oak Park with Online Reservations.

Weather in Oak Park, IL

View the weather forecast for Oak Park before booking your Oak Park Vacation Rentals to confirm your best time to go.

December - February
High 46°F       Low 20°F
March - May
High 68°F       Low 32°F
June - August
High 83°F       Low 62°F
September - November
High 80°F       Low 33°F

Activities Oak ParkGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Oak ParkGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Frank Lloyd Wright Home and Studio
Ernest Hemingway Museum and House
Oak Park Visitors Center
Oak Park Conservatory
Madison Street Theatre
Unity Temple
Frank Lloyd Wright Historic District
Mills Park
Pleasant Home
Moore House
Euclid Square Park
West Suburban Medical Center
Rush Oak Park Hospital
Navy Pier
Wrigley Field
McCormick Place
Millennium Park
Union Station
Soldier Field

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


West Suburban Medical Center 326 Properties
Frank Lloyd Wright Historic District 324 Properties
Frank Lloyd Wright Home and Studio 319 Properties
Madison Street Theatre 319 Properties
Rush Oak Park Hospital 317 Properties
Oak Park Visitors Center 313 Properties
Ernest Hemingway Museum and House 311 Properties
Mills Park 309 Properties
Euclid Square Park 309 Properties
Unity Temple 308 Properties
Pleasant Home 308 Properties
Oak Park Conservatory 307 Properties

Frequently Asked Questions About Oak Park?

What are the top hotels, lake houses & vacation rentals in Oak Park?

We provide an array of great vacation destinations in Oak Park. If you are looking to stay in or around the Oak Park area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Oak Park:

Which hotel, lake house, or vacation rental in Oak Park is best for families?

Searching for a family-friendly getaway in Oak Park? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Oak Park?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 182 in the Oak Park area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Oak Park.

Nearby Neighborhood (3) 
Neighborhood Property Count
Austin Vacation Rentals in Chicago, Illinois 159
South Austin Vacation Rentals in Chicago, Illinois 141
North Austin Vacation Rentals in Chicago, Illinois 456

People Also Ask

Online Reservation in Oak Park

Recently Booked Hotels, Resorts, or Rentals in Oak Park