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

Vacation rentals in Oak Park

Find 245 available vacation homes from 10 partners
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Top 15 Recommended vacation rentals in Oak Park

Find your perfect vacation rental in Oak Park from just $48 per night!

Apartment Oak Park
Apartment ∙ 7 guests ∙ 3 bedrooms

Apartment with garden & patio | Perfect for remote work

Oak Park, Oak Park Township, Illinois, United States
from $411
per night
Outstanding(6 ratings)
from $411
per night
View deal
Apartment Oak Park
Apartment ∙ 5 guests ∙ 2 bedrooms

Family-oriented rental apartment with BBQ | Suitable for remote work

Oak Park, Oak Park Township, Illinois, United States
from $127
per night
Outstanding(14 ratings)
from $127
per night
View deal
Apartment Oak Park
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-friendly lovely rental apartment with barbeque, patio & yard | Perfect for remote work

Oak Park, Oak Park Township, Illinois, United States
from $264
per night
Outstanding(2 ratings)
from $264
per night
View deal
Apartment Oak Park
Apartment ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful holiday apartment | Good for workation

Oak Park, Oak Park Township, Illinois, United States
from $308
per night
Excellent(33 ratings)
from $308
per night
View deal
Apartment Oak Park
Apartment ∙ 5 guests ∙ 2 bedrooms

Child-friendly lovely apartment with garden & patio | Lake view | Dogs allowed

Oak Park, Oak Park Township, Illinois, United States
from $115
per night
Excellent(58 ratings)
from $115
per night
View deal
Apartment Oak Park
Apartment ∙ 4 guests ∙ 3 bedrooms

Family-oriented lovely holiday apartment with terrace | Suitable for remote work

Oak Park, Oak Park Township, Illinois, United States
from $135
per night
Outstanding(19 ratings)
from $135
per night
View deal
Apartment Oak Park
Apartment ∙ 8 guests ∙ 3 bedrooms

Family-friendly beautiful rental apartment with BBQ & patio | City view | Suitable for remote work

Oak Park, Oak Park Township, Illinois, United States
from $251
per night
Outstanding(138 ratings)
from $251
per night
View deal
Apartment Oak Park
Apartment ∙ 4 guests ∙ 2 bedrooms

Fully equipped apartment with terrace

Oak Park, Oak Park Township, Illinois, United States
from $201
per night
Outstanding(54 ratings)
from $201
per night
View deal
Condo Oak Park
Condo ∙ 11 guests ∙ 3 bedrooms

Condo with garden

Oak Park, Oak Park Township, Illinois, United States
from $221
per night
Outstanding(4 ratings)
from $221
per night
View deal
House Oak Park
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly spacious house with terrace | Pets are welcome

Oak Park, Oak Park Township, Illinois, United States
from $516
per night
Very good(5 ratings)
from $516
per night
View deal
House Oak Park
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden & barbeque

Oak Park, Oak Park Township, Illinois, United States
from $186
per night
Outstanding(139 ratings)
from $186
per night
View deal
Apartment Oak Park
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday apartment with barbecue, garden & terrace

Oak Park, Oak Park Township, Illinois, United States
from $308
per night
Outstanding(32 ratings)
from $308
per night
View deal
House Oak Park
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented nice vacation home | Perfect for remote work

Oak Park, Oak Park Township, Illinois, United States
from $285
per night
Outstanding(34 ratings)
from $285
per night
View deal
Apartment Oak Park
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment with patio | Nature view | Suitable for remote work

Oak Park, Oak Park Township, Illinois, United States
from $150
per night
Excellent(2 ratings)
from $150
per night
View deal
Apartment Oak Park
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment | Suitable for remote work

Oak Park, Oak Park Township, Illinois, United States
from $221
per night
Excellent(110 ratings)
from $221
per night
View deal

Vacation rentals and apartments with air conditioning

House  Oak Park
from $278
per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, garden & grill

4.6
Excellent(39 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
View deal
House  Oak Park
from $346
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented vacation home with barbeque, yard & terrace | Good for workation

4.9
Outstanding(32 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
View deal
House  Oak Park
from $302
per night
House ∙ 6 guests ∙ 3 bedrooms

House with 3 rooms for 6 persons

4.9
Outstanding(34 ratings)
Oak Park, Oak Park Township, Illinois, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House  Oak Park
from $442
per night
House ∙ 12 guests ∙ 8 bedrooms

Children-friendly ample house with patio & barbeque

4.7
Excellent(3 ratings)
Oak Park, Oak Park Township, Illinois, United States
Balcony
View deal
House  Oak Park
from $544
per night
House ∙ 12 guests ∙ 6 bedrooms

Family-oriented vacation home with garden & patio

Oak Park, Oak Park Township, Illinois, United States
Balcony
View deal
Apartment  Oak Park
from $433
per night
Apartment ∙ 4 guests ∙ 3 bedrooms

Holiday apartment with 3 rooms for 4 persons

Oak Park, Oak Park Township, Illinois, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House  Oak Park
from $104
per night
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented house with terrace & garden | Perfect for remote work

3.7
Good(6 ratings)
Oak Park, Oak Park Township, Illinois, United States
Fireplace
View deal
Apartment  Oak Park
from $219
per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Children-friendly spacious rental apartment | Perfect for remote work

5.0
Outstanding(104 ratings)
Oak Park, Oak Park Township, Illinois, United States
Fireplace
View deal
House  Oak Park
from $221
per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with grill

5.0
Outstanding(1 rating)
Oak Park, Oak Park Township, Illinois, United States
Fireplace
View deal
See all offers

Budget-friendly Vacation Rentals in Oak Park

Find Fantastic yet Inexpensive Offers

House Oak Park
from $379
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with 4 rooms for 8 persons

4.8
Outstanding(15 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Apartment Oak Park
from $161
per night
Apartment ∙ 3 guests ∙ 1 bedroom

Family-friendly pleasant holiday apartment | Perfect for remote work | Pet-friendly

4.5
Excellent(49 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
House Oak Park
from $425
per night
House ∙ 12 guests ∙ 5 bedrooms

House with 5 rooms for 12 persons

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

Apartment Oak Park
from $317
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental apartment | Good for workation

4.8
Outstanding(4 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Apartment Oak Park
from $192
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday apartment | Perfect for remote work

5.0
Outstanding(2 ratings)
Oak Park, Oak Park Township, Illinois, United States
View deal
Apartment Oak Park
from $367
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-friendly charming apartment with garden & grill | City view | Perfect for remote work | Pet-friendly

5.0
Outstanding(1 rating)
Oak Park, Oak Park Township, Illinois, United States
View deal

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Popular Rental Amenities in Oak Park

  • Pet-friendly (63)
  • Pool (2)
  • WiFi (229)
  • Parking (24)
  • Balcony/patio (47)
  • TV (213)
  • Air conditioning (222)
  • Kitchen (217)
  • Fireplace (42)
  • Washing machine (162)
  • Smoking allowed (2)
  • Microwave (164)
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 245 rentals
🌙 Nightly prices starting at $48
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 63 homes

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 $48. Nightly prices for apartment rentals are $305 on average. House rentals in Oak Park cost $566 per night on average.

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

There are 245 rentals from 10 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 63 rentals in Oak Park that allow dogs and the average rate is $368 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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