
Holiday rentals in Rosemont
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Top-rated holiday rentals in Rosemont
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Best Deal in Chicago | Great Food & Free Parking
Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

Spacious Home Studio 10 Min From O’Hare & Rosemont
Clean and well appointed lower level of owner-occupied home with private in/out access separated from the main level. The suite-style space includes a generous living area with two large couches, 49” smart TV w/ sound system, king bed, full bathroom, kitchenette w/ table, washer/dryer & work desk. Great location 5-10 minutes from O'Hare, Allstate Arena, Rosemont and Rivers Casino with ample transportation options. Property is within short walking distance of grocery stores, gym, parks & more.

The Chicago River House – GIANT wall projector!
Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Rockin' 2Bed steps to shops/food/train
This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Spacious in-law Apt: 10 min to O'Hare and Downtown
Our family would love to share our in-law apt. (private entrance) in our Norwood Park house. A beautiful neighborhood, the convenience of O'Hare and the highway, and 3 ways to get downtown less than a mile away (blue line and metra). Great food, bars, grocery store, and parks all within walking distance. A great alternative to the hustle and bustle of the city but you can be in some of the best neighborhoods in the city in 15 min (Wicker Park, Lincoln Park, Logan Sq.) and downtown in 25.

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*

Modern Garden apartment (WHOLE UNIT)
Freshly Remodeled , Lower Level garden apartment one bedroom one bath. Older building with wooden floors. If hearing people upstairs walking can bother you , do NOT book it please .Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10min to outlets Absolutely NO parties, NO gathering Quiet hours 10 pm till 6.00 am

Romantic King Bed/1 free parking/O’hare/Allstate
-18 minutes to O’Hare/Allstate Arena -35 minutes to DT Chicago -King & QN 2 bedroom + sleeper sofa/1 bath apartment decorated with a playful & bright nautical theme & vintage accent pieces. -Board games, books, darts, & large screen TV for entertainment. -Tea & Coffee station -Free designated parking space -walk to local restaurants at corner or playground w/outside seating up the street. -Nothing fancy, but convenient! urban/suburbia vibe in quieter corner of busy central area

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.

Newly Renovated, Safe, 1 Bdrm, Self Check-in
This gorgeous first-floor apartment is located only 10 minutes from O'Hare International Airport. Located near Des Plaines River Road and Toughy Ave., you will be close to not only the airport but 7 minutes to Rivers Casino, 10 minutes from the Rosemont Entertainment District, and 30 minutes from downtown Chicago. The apartment is minutes away from two major highway interstates, which makes this a commuters ideal location.

Charming Chicago Apartment | Near O’Hare+Blue Line
Bright, private upstairs apartment in a quiet NW Chicago neighborhood—just 10 minutes from O’Hare and close to the Blue Line. Enjoy a comfy king bed, full kitchen, fast WiFi, and smart TV. Walking distance to shops, restaurants, and Harlem-Irving Plaza. Free street parking, private entrance, and self check-in make your stay easy and relaxed. Ideal for solo travelers, couples, or remote work.

Eddy Street Upstairs Apartment
Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!
Popular amenities for Rosemont holiday rentals
Other great holiday rentals in Rosemont

King Sleep Number Bed – No Cleaning Fee

Updated in May 2025 • Private Floor • Free Parking

Where Style and Substance Coexist. New Rehab

Freshly Remodeled Cozy 3 Bedroom Home

The Coziest Spot in Town

1BD Apt near O'Hare/Rosemont Allstate Arena

Chicago Addison St. 1 bed/1 bath condo, Garden Lvl

RR Oasis
Frequently Asked Questions
What are the most popular amenities for Hotel Rentals in Rosemont?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 30 homes with air conditioning, over 20 homes with a gym, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Rosemont?
Yes! Work meets play with ease at over 30 vacation rentals in Rosemont featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do hotel rentals in Rosemont have a gym?
Absolutely! We offer over 20 hotel rentals with a gym in Rosemont. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Rosemont?
Experience the best of Rosemont with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Rosemont have wifi?
Absolutely! We offer over 30 hotel rentals with wifi in Rosemont. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Rosemont?
Rosemont has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Rosemont have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Rosemont. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Rosemont?
Four-legged friends are welcome in Rosemont. Choose from more than 30 vacation rentals for guests traveling with pets.
Quick stats about holiday rentals in Rosemont

Total holiday rentals
Explore 40 holiday rentals in Rosemont

Nightly prices starting at
Rosemont holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 1,460 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Rosemont holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Rosemont rentals

4.6 Average rating
Rosemont stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Soldier Field
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wilmot Mountain Ski Resort
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Illinois Beach State Park
- The 606




