
Holiday rentals in Homewood
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Top-rated holiday rentals in Homewood
Guests agree: these stays are highly rated for location, cleanliness and more.

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer
PLEASE READ THE ENTIRE LISTING BEFORE BOOKING! LATE CHECKINS WELCOME! Enjoy FREE Washer/Dryer Full Kitchen + MORE! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more Illinois locations!

Charming Garden Apartment
Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Charming Homewood Away from Home
Keep it simple at this cozy, charming brick ranch tucked away on a quiet, friendly street. Just minutes from the Metra line for an easy ride into downtown Chicago, and close to all the great local shopping and dining in downtown Homewood. House Guidelines: • No smoking, no parties, no large gatherings • Be mindful of neighbors • Narrow driveway, limit 2 cars • No extra guests without notice • Pets are welcome, but must be added to your reservation • We have a moderate cancellation policy

Boulderstrewn: Historic Homewood home
Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

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.

Warm and comfortable inviting Suburban home !
160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

IT'S THE WRIGHT PLACE
Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Charming Unique 2 Bdrm Apartment in Victorian Home
My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Updated, bright, and modern, 3 bedroom home.
You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

Luv Happii House
Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.

Spruce Sanctuary
Welcome to this cozy, family-friendly 3BR home in the heart of Homewood, IL! Sleeps up to 8 with a brand-new kitchen, central heat & AC and fast WiFi -- ideal for work-from-home stays. Enjoy the fully fenced yard, perfect for kids and pets. Free driveway and street parking. Just minutes from parks, restaurants, and shopping. A perfect blend of comfort, convenience, and charm!

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more
GLAMPING FUN mid April - Nov RV w/bathroom - 2 beds 20' Safari Yurt - 5 beds Game Room w/queen, full & sofa sleeper Gazebo 2 twin beds Wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Mini golf; 3-n-1 bball/volley & pickleball court. Event Yurt add on $200 up to 15 additional non/overnight guest
Popular amenities for Homewood holiday rentals
Other great holiday rentals in Homewood

A Dream Home in Chicagoland

Luxurious townhome 30 days lease open for1-2 weeks

The Broadway Special - 2 Bd/1 Bath Smart-Condo!

Horizon - 4 BRs, 2 BA Game Room & Gym

Home away from home

Quiet 3BR Retreat • Walk to Wind Creek Casino

The Den: 2BR-1BT w/ 2 Living Rooms

Newly Remodeled Spacious home, fenced yard for dog
When is the best time to visit Homewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £158 | £147 | £134 | £133 | £158 | £157 | £147 | £149 | £120 | £137 | £139 | £135 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Frequently Asked Questions
How much does it cost to stay in house rentals in Homewood?
Experience the best of Homewood with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Homewood?
Homewood has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Homewood?
Four-legged friends are welcome in Homewood. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Homewood?
Yes! Work meets play with ease at over 20 vacation rentals in Homewood featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Homewood?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Homewood have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Homewood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Homewood have free parking?
Absolutely! We offer over 30 house rentals with free parking in Homewood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Homewood have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Homewood. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Homewood?
Make yourself at home in Homewood by choosing from our most frequently booked neighborhoods. We have over 160 vacation rentals in Homewood, over 100 vacation rentals in Flossmoor, and over 100 vacation rentals in East Hazel Crest.
Do house rentals in Homewood have wifi?
Absolutely! We offer over 30 house rentals with wifi in Homewood. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Homewood

Total holiday rentals
Explore 40 holiday rentals in Homewood

Nightly prices starting at
Homewood holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,280 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Homewood holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Homewood rentals

4.7 Average rating
Homewood stays receive an average rating of 4.7 out of 5 from guests
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Humboldt Park
- Soldier Field
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Washington Park Zoo
- The 606
- University of Chicago
- Chicago Cultural Center




