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Vacation rentals in Oak Brook

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Top-rated vacation rentals in Oak Brook

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Wood Dale

4.9 out of 5 average rating, 462 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Home in Oak Park

4.97 out of 5 average rating, 112 reviews

Clean, Cozy 1st Flr, 3 Beds, Kitchen, Free Parking

Enjoy our historic district two-flat w/ free parking in upscale, safe, walkable Oak Park just 3 blocks to the train for easy access to Chicago. Enjoy some tranquil time in our little urban farm. Check out the gardens and visit our 4 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties allowed. Minimum age to book, 25. Visit my profile for additional units.

Home in Berwyn

4.99 out of 5 average rating, 113 reviews

Retro Modern Bungalow— fire pit + free parking

Experience the city in style at Retro Modern Bungalow. The perfect crash pad for up to four friends and two pups. Featuring two spacious bedrooms, each w/ a king bed + luxury linens, a propane fire pit and a fully fenced backyard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Treehouse in Schaumburg

4.93 out of 5 average rating, 770 reviews

Enchanted Garden Treehouse (Amenity*)

Fall is here, the trees are beginning to turn, and the treehouse is warm and cozy! Relax on cool evenings in our luxurious, very private, new 4' deep cedar hot tub nestled in the evergreens, while the stars and moon swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits and even foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

Rental unit in Forest Park

4.99 out of 5 average rating, 139 reviews

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

Guest suite in Chicago

4.98 out of 5 average rating, 137 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Rental unit in Aurora

4.99 out of 5 average rating, 105 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this brand new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Guesthouse in Lake Forest

4.95 out of 5 average rating, 115 reviews

The Green Door - safe and calm with walkability

This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

Guest suite in St. Charles

5 out of 5 average rating, 274 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Rental unit in Forest Park

4.97 out of 5 average rating, 118 reviews

1 bedroom garden apartment in Forest Park

Unique private garden apartment in our single family residence. Great location approximately 8 miles directly west of downtown Chicago. Close to shopping, dining, entertainment and public transportation to the city. One bedroom and best for 2 people but could sleep 3 for short stays. It's important to note that this is a garden/ground/lower level apartment. The ceilings are relatively low at 6.5'. This would not be the best space for tall people. Street parking in front of the house.

Guest suite in Naperville

4.95 out of 5 average rating, 375 reviews

Lake facing cozy little studio with private entry

This is a luxurious cozy little studio facing the lake, featuring a private entrance that is attached to a single family home. The studio is equipped with a top quality queen bed, an in-suite kitchenette including a mini fridge, microwave, and induction top, as well as a luxurious full bathroom. The studio is situated in the safest and friendliest neighborhoods in Naperville conveniently located close to cafes, restaurants, markets, a biking trail, and just minutes away from I88.

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 319 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

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Popular amenities for Oak Brook vacation rentals

Free parking on premises

Air conditioning

Stay near Oak Brook's top sights

Oakbrook Center35 locals recommend

Oakbrook Mall station11 locals recommend

Trader Joe's9 locals recommend

Yorktown Center8 locals recommend

AMC DINE-IN Yorktown 187 locals recommend

Chipotle Mexican Grill6 locals recommend

Other great vacation rentals in Oak Brook

Rental unit in Forest Park

4.88 out of 5 average rating, 82 reviews

City-Accessible Basement Retreat

Villa in Westmont

4.79 out of 5 average rating, 43 reviews

Westmont,Il Duplex - Side B. In law suite 1/1

Home in Lombard

4.99 out of 5 average rating, 93 reviews

Modern Boho house in Lombard 7 min to Metra

Rental unit in Chicago

4.95 out of 5 average rating, 60 reviews

Serene Escape with King Sleep Number Bed, No Fees!

Home in Downers Grove

4.96 out of 5 average rating, 24 reviews

Lakefront Getaway Home! Lots of Fun! Win.Discount$

Rental unit in Downers Grove

5 out of 5 average rating, 10 reviews

Cozy Apartment in Downtown

Home in Lombard

5 out of 5 average rating, 15 reviews

Spacious Home in Chicago Suburbs

Guest suite in Naperville

5 out of 5 average rating, 77 reviews

Beautiful, quiet, private, spacious, guest suite.

Quick stats about vacation rentals in Oak Brook

Total rentals
20 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
540 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

Do house rentals in Oak Brook have wifi?
Absolutely! We offer over 10 house rentals with wifi in Oak Brook. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Oak Brook?
Oak Brook has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Oak Brook?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Oak Brook have free parking?
Absolutely! We offer over 10 house rentals with free parking in Oak Brook. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Oak Brook?
Yes! Work meets play with ease at over 10 vacation rentals in Oak Brook featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Oak Brook have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Oak Brook. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oak Brook have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Oak Brook. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Oak Brook?
Experience the best of Oak Brook with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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