Photo by Erik Rowley

Oak Forest Holiday Rentals

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Holiday Rentals in Oak Forest

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (425)
"I just wish that the valet parking wasn’t $75 a night! What a nightmare! Asides from that, it’s super clean and super easy to check in, and there’s an infinity pool!"
The price is NZ$388
per night
1 Jul - 2 Jul
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (94)
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is NZ$163
per night
30 Jun - 1 Jul
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (309)
"Sonder rocks!"
The price is NZ$355
per night
9 Jun - 10 Jun
Sonder South Wabash
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Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (76)
"Small studio with queen bed and good kitchen facilities. Design very basic / post-industrial (with exposed pipes and wires)."
The price is NZ$472
per night
30 Jun - 1 Jul
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (34)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (106)
"Loved it "
The price is NZ$424
per night
18 Jun - 19 Jun
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (162)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$373
per night
2 Jul - 3 Jul
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
LakeHouse
10.0 out of 10, Exceptional, (7)
"Great"
LakeHouse
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (8)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Chic Suite/Mins to L Train /Laundry/Free Parking
9.4 out of 10, Exceptional, (18)
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
Chic Suite/Mins to L Train /Laundry/Free Parking
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (20)
"It was an amazing property so quiet and calm area lovely host super great with communication and answering any questions I had"
The price is NZ$558
per night
12 Jun - 13 Jun
national historic home near downtown airports no parties no events
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (29)
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is NZ$452
per night
2 Jul - 3 Jul
Sonder Greektown
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (179)
"This place is charming! The flat is lovely and very comfortable. We enjoyed the neighborhood, the park next door, the restaurants one street over, close to grocery store and a few minute walk to jump on the train. We would love to return in the future!"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Million Dollar Views! Luxury Downtown Skyhouse!
10.0 out of 10, Exceptional, (92)
"WOW! That's what we say about this place. My family and I loved it! The location and the views-WOW! It is floor to ceiling windows in the living room and the bedrooms. Absolutely so cool. We were met when we arrived, shown the parking space for our car-a great space and totally worth having one. Then taken up to our floor-the elevators are quick and smooth. It was easy to get in and out--we used uber and it was super easy for them-close to everything, a fantastic location. The A/C worked well...
The price is NZ$2,164
per night
18 Jun - 19 Jun
Million Dollar Views! Luxury Downtown Skyhouse!
Stay in the Heart of the City! Complimentary Bicycles for exploring!
10.0 out of 10, Exceptional, (2)
"Enjoyed the walkability of this location to all downtown Chicago has to offer. The onsite amenities were also wonderful"
The price is NZ$442
per night
30 Jun - 1 Jul
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (62)
"Really fun neighborhood with unexpected street fair & very cute apartment."
Stay in “STYLE” Apartment, close to CHI downtown
LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, (10)
"Our team had a one day conference in Chicago. Although it was near the highway it wasn't very loud. Decent neighborhood and the good part is that it was near the highway. Lower level bed is uncomfortable, no other way to say that. I still give it 5-stars as it is as advertised. Communication with owner was timely."
The price is NZ$500
per night
6 Jun - 7 Jun
LUXE 3 BR, 2 BA + Hot Tub
Don't see what you're looking for?
See all available properties in Oak Forest
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Oak Forest you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6848)
"I like the location."
The price is NZ$282
per night
16 Jun - 17 Jun
Congress Plaza Hotel
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3079)
"Front desk help was amazing"
The price is NZ$306
per night
1 Jul - 2 Jul
Club Quarters Hotel, Central Loop, Chicago
Travelodge by Wyndham Downtown Chicago
2.0 star property
6.4 out of 10, (1699)
"The metro train passes next to the building. If you’re not a hard sleeper, it could get annoying "
The price is NZ$231
per night
1 Jul - 2 Jul
Travelodge by Wyndham Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oak Forest holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oak Forest. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oak Forest. Seeing all the best attractions is bound to make you fall in love with Oak Forest. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oak Forest short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Oak Forest?

Yes, there are holiday rentals close to the most popular sights in Oak Forest, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Oak Forest. Make sure you have time to check out the forests and live music during your trip.

What are some of the best holiday rentals that Oak Forest has to offer?

Luxury Home Away From Your Home: This holiday home rental outside of Oak Forest has air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Oak Forest?

Explore the area and family-friendly sights such as Odyssey Fun World, or get out into nature at a spot like Centennial Park. Gaelic Park and George Dunne National Golf Club are other places to visit while you're in town.

What are holiday rentals like in Oak Forest?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Forest. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.

Recent reviews of Oak Forest properties
Expedia verified reviews