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

Home in Homewood
4.72 out of 5 average rating, 71 reviewsA Dream Home in Chicagoland
DemetraRating, 5 stars4 weeks ago
I have been staying at this property for 5 months. My continued stays is a great indicator of pleasure with the location and the host. Farrah is very responsive. The home is always clean. This place is in a great location - close to restaurants, grocery stores, and the interstate. Other than the yard needing to have some maintenance, it was a great stay as always.
Guest favourite

Home in South Holland
4.78 out of 5 average rating, 27 reviewsLast-Minute Romantic Escape | Perfect for Couples
AlexisRating, 5 stars1 week ago
Nicole was very helpful and friendly. Her place was clean and looked like the pictures posted. I would definitely recommend this listing.
Guest favourite

Home in Orland Hills
4.95 out of 5 average rating, 20 reviewsOrland hill’s rental
VictoriaRating, 5 stars3 weeks ago
We really enjoyed our stay here! There was plenty of space for 6 adults and a child with many places to hang out. The neighborhood was nice and the house was very clean. It was great to spend time in the backyard with the nice weather we had.

Home in Glenwood
4.75 out of 5 average rating, 16 reviews5min to Wind Creek Casino/Fast Wi-Fi/Comfy beds
TerranceRating, 5 stars3 weeks ago
Great place to stay with family. Great location if you need a place near the Chicago south suburbs. Clean home and the host was super friendly and accommodating to us. Would definitely stay again.

Home in Tinley Park
4.5 out of 5 average rating, 4 reviewsLuxury Townhome in Tinley Park Near Shops & Train
StevetteRating, 5 stars3 weeks ago
The home was a beautiful place. The Host was super helpful. My Family and I arrived Hours early ( 11:00a.m) and was aloud to check in once we had arrived. Danita was so helpful I truly appreciated the communication. The home was lovely, warm and cozy. The home was spacious and pleasing. I so recommend staying here. Because once I return back to Chicago I will be rebooting myself another stay. Thank you again Danita for being a fantastic Host
Top Guest favourite

Home in Munster
4.98 out of 5 average rating, 54 reviewsCozy Farmhouse in Munster
JenniferRating, 5 stars5 days ago
A wonderful cottage, it was tucked away in a quiet neighborhood. The “home away from home”, was nicely appointed with furniture, linens, kitchen tools and utensils. The hostess was very responsive, helpful and friendly. Check-in was smooth and directions were clear. Beds were comfortable and we thoroughly enjoyed our stay. When we have an opportunity to be in the area again we will definitely see if this house is available! Till next time!

Home in Homewood
4.74 out of 5 average rating, 99 reviewsCottage Feel 2 bedroom Home!
SusanRating, 5 stars6 months ago
Love this cozy cottage type home. Very comfortable and great location in Homewood and easy access to Metra. Enjoy walking in the neighborhood, felt very safe! Marcia is WONDERFUL, very nice person & superb hostess!
Guest favourite

Home in Homewood
5 out of 5 average rating, 10 reviewsCharming 2BR with Fireplace
StaceyRating, 5 stars2 days ago
This house has everything you want or need. It was warm and inviting. We enjoyed it so much we didn't want to leave. We loved the yard and the art in the house. Even the neighbors were friendly. Only Jesus is perfect. This house is excellent. Thank you so much for everything.
Quick stats about holiday rentals in Homewood
Total rentals
40 properties
Total number of reviews
950 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
- Chicago Cultural Center
- Medinah Country Club