Holiday rentals in Hillside

4.94 out of 5 average rating, 123 reviews

Flat in Melrose Park

KNG+QN 2bdrm/1parking space /18 min O’hare/Alstate

Top/2nd floor apartment+ parking spot in adjacent lot & playground up street Shampoo & body wash, extra towels, coffee & tea, WI-FI, books & board games, fully stocked kitchen for cooking, toaster oven, ice, iron & iron board, workspace, large screen TV 17 min-airport 18 min-Allstate arena 30 min-DT Chicago Early check-in/late checkout possible Walk to restaurants & bars/shopping & groceries/movie theater & Plaza 3 grocery stores within 10 min walk. Oak Brook/Oak Park/Rosemont shopping~ 20 min

4.91 out of 5 average rating, 501 reviews

Guest suite in Wood Dale

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 .

4.85 out of 5 average rating, 168 reviews

Flat in Hillside

Easy, Cool, safe place to stay.

Level 1 car charging available, message me. 17 mins Ohare airport 25 mins to downtown Chicago I want you to enjoy your stay, and I don't have rules other than basic ones like noise and guest limit. Have Fun Very safe and quiet 420 might be ok, please message me* 3 Queen-size beds. One is self-iflating inside the middle closet. Well stocked kitchen 2 Private parking lot spaces. Kreuger coffee 2 tvs Netflix There is no smoking in the unit or inside building* Coin laundry is available

4.97 out of 5 average rating, 30 reviews

Flat in Westchester

Short Drive to Hospitals/Airports/Downtown Chicago

This centrally located spacious basement apartment is 10-15 miles from Elmhurst Hospital, Loyola Med, and Downtown Chicago. Whether you are exploring the BEST BIG CITY as awarded by Condé Nast Traveler or just stopping through on your journey, this home has everything you and your family need to feel right at home in Chicago. Minutes to downtown LaGrange, the sprawling Rosemont entertainment district, and the fabulous outdoor Oak Brook Mall with tons of shopping, entertainment, and restaurants.

4.87 out of 5 average rating, 119 reviews

Flat in Forest Park

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Guest suite in Brookfield

5 out of 5 average rating, 103 reviews

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.82 out of 5 average rating, 123 reviews

Flat in Oak Park

Circle Back Modern Apartment

Sit on your leafy private patio and enjoy your coffee before heading out to the city- or wind down at the end of the day with a cold beer. Steps to coffee shops, neighborhood pubs, and the Blue Line train this beautifully updated and decorated apartment is the perfect landing pad for your Chicago adventure. FREE off-street parking, free in-unit laundry, a cute coffee station- basically every amenity we could think of! This will be the place you want to stay every time you visit Chicago.

4.97 out of 5 average rating, 102 reviews

Home in Westchester

Jacuzzi, King Beds, Easy Access to DT Chicago!

Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs (w/ complimentary Hulu & Disney+), a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!

4.92 out of 5 average rating, 101 reviews

Flat in Maywood

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

5 out of 5 average rating, 4 reviews

Flat in Berwyn

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Guest house in Villa Park

4.92 out of 5 average rating, 121 reviews

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

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Other great holiday rentals in Hillside

Private room in Willow Springs

4.93 out of 5 average rating, 278 reviews

Private bedroom A in a quiet Chicago suburb.

RodrigoRating, 5 stars1 week ago

Had a nice time, was flexible about parking spots.

4.94 out of 5 average rating, 305 reviews

Private room in Oak Park

Single bedroom with Asian decor in family home

MichaelRating, 5 stars5 days ago

A very nice house close to the metro and in a peaceful suburb. John and Daniel was very welcoming hosts and gave me helpful hints on places to eat in the local area.

Private room in Richton Park

4.85 out of 5 average rating, 241 reviews

Urbal retreat

RobertRating, 5 stars1 week ago

The host was great, we loved the cozy room and amenities. The shower was very clean and nice. Great spot for if you’re just passing through.

4.87 out of 5 average rating, 174 reviews

Hotel room in Itasca

Guest room with 2 Double Beds + PET Friendly

JasonRating, 5 stars2 weeks ago

Beautiful property, great room, and AMAZING pool! Such a deal for the price and everything. Love it. Will come back for sure!

4.87 out of 5 average rating, 55 reviews

Private room in Berwyn

The Quilt Room. Micro-flower farm.

TaliahRating, 5 stars2 weeks ago

The home was perfect for our trip to chicago! We will definitely come back again

Private room in Woodridge

4.86 out of 5 average rating, 499 reviews

Private floor with Bedroom, bathroom, living rm

NecoleRating, 5 stars6 days ago

Taylor's place was very nice; she really thought of everything. Everything you could need was there; Taylor makes you feel right at home. The neighborhood is nice and you're close to a number of things. Oh and the shower pressure was great!

Private room in Norwood Park

4.8 out of 5 average rating, 223 reviews

Skyline Room, near Medical Ctr, Upstairs

ThoRating, 5 stars5 months ago

Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.