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Holiday houses in Oak Park

Find and book unique accommodation on Airbnb

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Popular amenities for Oak Park holiday rentals

Stay near Oak Park's top sights

Frank Lloyd Wright Home and Studio184 locals recommend
Classic Cinemas Lake Theatre72 locals recommend
Ernest Hemingway Birthplace Museum70 locals recommend
Maya Del Sol67 locals recommend
FitzGerald's62 locals recommend
Spilt Milk57 locals recommend

Other great holiday rentals in Oak Park

Guest favourite

Home in West Lawn

4.94 out of 5 average rating, 32 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

MadisonRating, 5 stars1 month ago
Lovely place to meet up with friends!
Guest favourite

Apartment in West Town

4.85 out of 5 average rating, 126 reviews

Condo with private terrace, free WIFI and parking

AaronRating, 5 stars6 months ago
Great place, very clear and easy instructions, close to everything you need in the city, made a mistake with booking and they made it extremely easy and very flexible to stay an extra night.
Superhost

Home in Schaumburg

4.8 out of 5 average rating, 79 reviews

Spacious 5 Bedroom 1 Level Renovated Modern House

MarshaRating, 5 stars1 month ago
The house itself was great. We loved the space and the game room was a big hit. We had plenty of room for our family Christmas. We also appreciated the pet friendly amenity.
Guest favourite

Apartment in Albany Park

4.95 out of 5 average rating, 39 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars3 weeks ago
Thank you for letting us stay in your beautiful home. Everything was exactly as described! Will definitely stay again
Superhost

Apartment in Jefferson Park

4.81 out of 5 average rating, 16 reviews

City Gem: Stylish 3BR for Urban Explorers

MaríaRating, 5 stars1 month ago
Excellent lodging and host, I would come back!
Guest favourite

Home in Lockport

5 out of 5 average rating, 19 reviews

Cozy 4 Bed Ranch w Fenced Yard *Netflix

StephanieRating, 5 stars1 week ago
Samantha’s home was a great landing spot in an easy location for us to visit with nearby family. Five adults and one toddler were very comfortable and enjoyed the space. The house is well appointed with everything we needed, and we appreciated the extra toys and high chair. The neighborhood is quiet and peaceful, while being near amenities and major highways. The listing description, Samantha’s instructions, and the posted instructions in the house made for a seamless stay.
Superhost

Condo in East Rogers Park

4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars1 month ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Guest favourite

Home in Lombard

5 out of 5 average rating, 21 reviews

Spacious Home in Chicago Suburbs

JonathanRating, 5 stars1 week ago
Fantastic spot. Came for a local event with some friends and definitely was not disappointed. Made my first ever Airbnb experience super easy and low stress.

Quick stats about holiday rentals in Oak Park

  • Total rentals

    330 properties

  • Total number of reviews

    18K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    320 properties include access to Wi-Fi

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Oak Park