Vacation rentals in Oak Park - HomeToGo base64Hash Vacation rentals in Oak Park - HomeToGo

Vacation rentals in Oak Park

Find 337 available house rentals from 9 partners
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1 guest
Anytime
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Top 15 Recommended vacation rentals in Oak Park

Find your perfect vacation rental in Oak Park from just $37 per night!

Condo Oak Park
Jul 12 - Jul 19
Condo ∙ 5 guests ∙ 3 bedrooms

Condo | Suitable for Remote Work

Oak Park, Oak Park Township, Illinois, United States
$134
per night
Outstanding(61 ratings)
$134
per night
View deal
Apartment Oak Park
Jul 12 - Jul 19
Apartment ∙ 5 guests ∙ 2 bedrooms

Family-Friendly Pleasant Rental Apartment with Garden & Patio | Perfect for Remote Work

Oak Park, Oak Park Township, Illinois, United States
$234
per night
Excellent(22 ratings)
$234
per night
View deal
Apartment Oak Park
Jul 5 - Jul 12
Apartment ∙ 8 guests ∙ 3 bedrooms

Child-Friendly Big Apartment with BBQ & Patio | City View | Good for Workation

Oak Park, Oak Park Township, Illinois, United States
$263
per night
Outstanding(125 ratings)
$263
per night
View deal
Apartment Oak Park
Jul 12 - Jul 19
Apartment ∙ 3 guests ∙ 2 bedrooms

Holiday Apartment with Garden

Oak Park, Oak Park Township, Illinois, United States
$228
per night
Outstanding(85 ratings)
$228
per night
View deal
Condo Oak Park
Jun 28 - Jul 5
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with 3 Rooms for 7 Persons

Oak Park, Oak Park Township, Illinois, United States
$213
per night
Excellent(36 ratings)
$213
per night
View deal
Apartment Oak Park
Jun 28 - Jul 5
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment with Terrace

Oak Park, Oak Park Township, Illinois, United States
$193
per night
Outstanding(21 ratings)
$193
per night
View deal
House Oak Park
Mar 3 - Mar 10
House ∙ 8 guests ∙ 3 bedrooms

Family-Friendly Charming House with Yard | Perfect for Remote Work | Dogs Allowed

Oak Park, Oak Park Township, Illinois, United States
$205
per night
Excellent(35 ratings)
$205
per night
View deal
House Oak Park
Jun 28 - Jul 5
House ∙ 6 guests ∙ 3 bedrooms

House with Yard | City View | Good for Workation

Oak Park, Oak Park Township, Illinois, United States
$272
per night
Outstanding(17 ratings)
$272
per night
View deal
Apartment Oak Park
Jul 12 - Jul 19
Apartment ∙ 5 guests ∙ 3 bedrooms

Child-Friendly Wonderful Holiday Apartment | Good for Workation

Oak Park, Oak Park Township, Illinois, United States
$206
per night
Outstanding(103 ratings)
$206
per night
View deal
House Oak Park
Jul 12 - Jul 19
House ∙ 5 guests ∙ 2 bedrooms

Family-Friendly Lovely Vacation Home with BBQ & Pool

Oak Park, Oak Park Township, Illinois, United States
$194
per night
Outstanding(16 ratings)
$194
per night
View deal
Apartment Oak Park
Jun 7 - Jun 14
Apartment ∙ 8 guests ∙ 4 bedrooms

Apartment | Nature View

Oak Park, Oak Park Township, Illinois, United States
$341
per night
Outstanding(4 ratings)
$341
per night
View deal
House Oak Park
Jul 5 - Jul 12
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home with 2 Rooms for 4 Persons

Oak Park, Oak Park Township, Illinois, United States
$260
per night
Outstanding(4 ratings)
$260
per night
View deal
House Oak Park
Jul 12 - Jul 19
House ∙ 4 guests ∙ 2 bedrooms

House with Garden | Suitable for Remote Work

Oak Park, Oak Park Township, Illinois, United States
$126
per night
Outstanding(7 ratings)
$126
per night
View deal
House Oak Park
Jun 14 - Jun 21
House ∙ 6 guests ∙ 3 bedrooms

House with Garden & Barbecue

Oak Park, Oak Park Township, Illinois, United States
$196
per night
Outstanding(138 ratings)
$196
per night
View deal
House Oak Park
-43%
Jul 6 - Jul 13
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home with 4 Rooms for 6 Persons

Oak Park, Oak Park Township, Illinois, United States
$482$291
per night
Outstanding(32 ratings)
$482$291
per night
View deal

Vacation Rentals With Fireplaces

House  Oak Park
Jan 4 - Jan 11
-81%
$595
$224
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Lovely House

5.0
Outstanding(3 ratings)
Oak Park, Oak Park Township, Illinois, United States
Free cancellation
Fireplace
View deal
House  Oak Park
Jan 5 - Jan 12
$270
per night
House ∙ 10 guests ∙ 4 bedrooms

House with Fast Internet & Yard

Oak Park, Oak Park Township, Illinois, United States
Free cancellation
Fireplace
View deal
House  Oak Park
Dec 28 - Jan 4
$161
per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home with BBQ & Yard

5.0
Outstanding(7 ratings)
Oak Park, Oak Park Township, Illinois, United States
Free cancellation
Fireplace
View deal
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Best Vacation Home Deals in Oak Park

Save up to 72%

House Oak Park
Apr 5 - Apr 12
-72%
$643
$276
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Friendly Big House | Perfect for Remote Work

4.8
Outstanding(31 ratings)
Oak Park, Oak Park Township, Illinois, United States
Free cancellation
View deal
Apartment Oak Park
Sep 13 - Sep 20
-18%
$303
$181
per night
Apartment ∙ 8 guests ∙ 1 bedroom

Fully Equipped Apartment with Yard | Garden View | Good for Workation

4.7
Excellent(6 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Bed and breakfast Oak Park
Jan 11 - Jan 18
-18%
$333
$273
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wonderful Bed and Breakfast for 2 Persons

4.8
Outstanding
Oak Park, Oak Park Township, Illinois, United States
View deal

Choose among 337 vacation homes featured in Oak Park and find a welcoming home for your getaway. Using HomeToGo you can instantaneously search and compare the prices of each listed rental to find the best price and save up to 72%.

Budget-friendly Vacation Rentals in Oak Park

Find Fantastic yet Inexpensive Offers

House Oak Park
Jul 12 - Jul 19
$261
per night
House ∙ 5 guests ∙ 2 bedrooms

House with 2 Rooms for 5 Persons

4.7
Excellent(6 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Apartment Oak Park
Jul 8 - Jul 15
$153
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment | Suitable for Remote Work

4.5
Excellent(22 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Apartment Oak Park
Jul 19 - Jul 26
$224
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Holiday Apartment with Garden | Good for Workation | Pet-Friendly

4.8
Outstanding(10 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal

Top-Rated Rentals and Accommodations in Oak Park

Book Vacation Rental Offers with the Highest User Rating

House Oak Park
Jul 19 - Jul 26
$648
per night
House ∙ 14 guests ∙ 6 bedrooms

Family-friendly vacation home with garden & BBQ | Perfect for remote work | Pets are welcome

4.9
Outstanding(21 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Apartment Oak Park
Jul 12 - Jul 19
$201
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with 3 rooms for 6 persons

4.8
Outstanding(99 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Condo Oak Park
Feb 20 - Feb 27
$156
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly condo

4.6
Excellent(43 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal

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Popular Rental Amenities in Oak Park

  • Pet-friendly (69)
  • Pool (4)
  • WiFi (314)
  • Parking (36)
  • Balcony/patio (47)
  • TV (279)
  • Air conditioning (302)
  • Kitchen (302)
  • Fireplace (64)
  • Washing machine (180)
  • Smoking allowed (5)
  • Microwave (224)
What are the best activities for families in Oak Park?

Oak Park spurs the imagination

Because Oak Park offers a small-town feel, family-friendly activities are plentiful. From communing with nature to fostering your child's imagination, Oak Park always has something up its sleeve on those days when your kids are bored and you're out of ideas!

Established in 1929, the Oak Park Conservatory boasts 3 different greenhouses; one dedicated to the desert, tropical and Mediterranean landscapes. Some of their plants are over 80 years old. Age-appropriate workshops and field trips are scheduled regularly, along with wine nights for the parents

About a 10-minute drive from the downtown area, you will find a treasure for kids: Wonder Works. This hands-on children's museum fosters learning through art, performance, design, and building. With interactive imaginary play areas and an organic garden, children will thrive in this haven for playful learning.

Oak Park is a diverse town. While it may seem that Chicago overshadows the perks of this municipality, "the OP" holds it own!

What are the best places to discover the arts and culture of Oak Park?

Turn-of-the-century architecture

Oak Park was home to the premiere architects of America's Prairie School, including Louis Sullivan, George W, Maher, and most famously Frank Lloyd Wright. Of course, this makes the street scenes of Oak Park an inspiring setting of living history.

A 15-minute walk from downtown will lead you to Frank Lloyd Wright's lodgings and office. The museum provides an intimate portrayal of the Mission Movement creator – he designed his home with clean edges, expansive spaces, and open layouts. Daily tours will walk you through the life of the famed architect.

You can also tour the Maher-designed Pleasant Home on the south side of town. It is the only building of his open to the public. His Prairie style was a precursor to Wright's simplistic methods – creating that basic frame of straight lines and smooth curves with minute details. The site regularly hosts live music from touring and local musicians, lectures, and various film screenings.

Information about vacation rentals in Oak Park

🏡 Vacation rentals available 337 rentals
💳 Possible discounts up to 72%
🌙 Nightly prices starting at $37
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 70 homes
7,166 reviews
Oak Park vacation rentals have an average rating of 4.7/5 on 7,166 reviews left by travelers.

Frequently Asked Questions

What is the typical price per night for a vacation rental in Oak Park?

The nightly price of accommodations in Oak Park starts at $37. Nightly prices for apartment rentals are $282 on average. House rentals in Oak Park cost $450 per night on average.

How many vacation homes are available to book in Oak Park?

There are 337 rentals from 9 different providers in Oak Park.

What are the most popular amenities for vacation rentals in Oak Park?

The most popular amenities for vacation rentals in Oak Park include accommodations that have: Pets allowed, Pool, and Internet.

Are pets allowed in vacation homes in Oak Park?

Sure, currently there are 70 rentals in Oak Park that allow dogs and the average rate is $329 per night.

What's the best time of year to travel to Oak Park?

If you are booking a vacation home in Oak Park, consider that rainy season is typically in December or January, with September often being the driest.

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