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Compare 187 Vacation Homes in Homewood with updated reviews, rates, and availability.

Woodlawn Oasis...10 Minutes to Dining & Downtown
Living area

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Living area

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

10.0 out of 10, Exceptional, (2)
"The property was very nice and spacious. The location was great and the parking in the back was amazing. We felt safe and happy our whole stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
LakeHouse
Game room

LakeHouse

10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse
Full Luxurious Modern House Near Chicago
Living area

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Matteson Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | Stairs Required

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago
Dreamsville Gateway to Indiana Dunes National Park
Private kitchen

Dreamsville Gateway to Indiana Dunes National Park

6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Room

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean in a safe neighborhood. I would stay here again"
The price is SAR 597
SAR 820 total
includes taxes & fees
27 Dec - 28 Dec
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Spacious Luxury Retreat 7 Bed Oasis with 5 Baths

Spacious Luxury Retreat 7 Bed Oasis with 5 Baths

9.6 out of 10, Exceptional, (15)
"Property was as listed, great communication, great location near city center"
Spacious Luxury Retreat 7 Bed Oasis with 5 Baths
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

8.6 out of 10, Excellent, (7)
"A very nice experience "
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

10.0 out of 10, Exceptional, (15)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Terrace/patio

Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!

9.8 out of 10, Exceptional, (14)
"Nigam and Wendy were excellent! The place was great! It was equipped with everything for a large group staycation! Very close to Chinatown and Chicago downtown! We loved our stay! Highly recommend Elegant Mayor's Manor!"
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.6 out of 10, Excellent, (4)
"Overall it was a great experience and I’ll be coming back sooner"
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Cedar Sunrise-1 BR Lake House
Property grounds

Cedar Sunrise-1 BR Lake House

10.0 out of 10, Exceptional, (14)
"…for me. Clean, cozy, close to everything, quiet and well appointed. This was my second stay and I will continue to return for my family holiday visits. Comfy bed with great pillow’s! "
Cedar Sunrise-1 BR Lake House
Renovated Griffith Family Home in Chicagoland Area
Griffith Vacation Rental | 3BR | 2.5BA | Step-Free Entry | 1,753 Sq Ft

Renovated Griffith Family Home in Chicagoland Area

10.0 out of 10, Exceptional, (19)
"House was a perfect place for our family (and dog:) to stay for our son’s wedding in Munster. Loved the kitchen area to gather with our family. Snacks, fruit and water upon arrival were a nice bonus. Great communication with host."
Renovated Griffith Family Home in Chicagoland Area
Cedar Sunset On the Lake
Miscellaneous

Cedar Sunset On the Lake

10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed our stay at Cedar Sunset on the Lake! The home was extremely clean and provided every necessity that you could ever need! The bed and furnishings were extremely comfortable and by far the best I’ve experienced in a rental property. The lake was right out the back door and we spent a lot of time on the dock while the kids were always in the lake and provided paddle board. The home was also in close proximity to Crown Point, but the town of Cedar Lake offered everything...
Cedar Sunset On the Lake
CentralChgo/2BR1Bath/PublTrans/Wifi/Garage/Laundry
Living area

CentralChgo/2BR1Bath/PublTrans/Wifi/Garage/Laundry

2.0 star property
CentralChgo/2BR1Bath/PublTrans/Wifi/Garage/Laundry
Staycation Retreat
Living area

Staycation Retreat

2.0 star property
9.0 out of 10, Wonderful, (2)
"Had a great time with my girls."
The price is SAR 440
SAR 913 total
includes taxes & fees
4 Jan - 5 January 2025
Staycation Retreat
Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi
Private kitchen

Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi

2.0 star property
10.0 out of 10, Exceptional, (4)
"This updated home is immaculate and had all the items necessary to move in and enjoy a family vacation for 3 days. The kitchen is well appointed with a gas range and all cookware that is needed. The bathrooms are well stocked with towels. Check in and checkout was easy. We appreciated finding this place to stay close to family who live in the area."
Luxury 4-bedroom home in beautiful Willowbrook Forest Preserve area with AC WiFi
Secluded Crown Point Haven Near Golfing & Parks!
Crown Point Vacation Rental | 4BR | 2BA | 3 Steps to Enter | 1,736 Sq Ft

Secluded Crown Point Haven Near Golfing & Parks!

2.0 star property
Secluded Crown Point Haven Near Golfing & Parks!
Charming 3-bedroom house in Calumet City with WiFi and AC
Living area

Charming 3-bedroom house in Calumet City with WiFi and AC

10.0 out of 10, Exceptional, (1)
"It was pretty fun and a good place it had a lot of space for everyone and could get around it."
The price is SAR 563
SAR 1,074 total
includes taxes & fees
24 Jan - 25 January 2025
Charming 3-bedroom house in Calumet City with WiFi and AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Homewood

Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

10.0 out of 10, Exceptional, (15)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!
Living area

Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!

10.0 out of 10, Exceptional, (6)
"Clean & Convenient "
Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!
A Dream Home in Chicagoland

A Dream Home in Chicagoland

4.8 out of 10, (3)
"The house is very old, however, the owners have made updates that make it comfortable. Very clean inside. The kitchen and bathroom is well stocked. The neighborhood is very well kept and people/neighbors are very friendly. I would recommend for adults or corporate stays just because the stairways are a little steep and lacking in handrails. Had a great experience with the host which means a lot to me when I book a vacation rental."
A Dream Home in Chicagoland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.