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

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

Staycation Retreat

2.0 star property
9.4 out of 10, Exceptional, (3)
"Had a great time with my girls."
The price is AED 430
AED 876 total
includes taxes & fees
12 Jan - 13 Jan
Staycation Retreat

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (17)
"For the most part this was a great place to stay. If you want to be in the south suburbs this is ideal for getting to other places in other burbs or to the city. Our only caveat would be it should be emphasized that this is a much better property for two rather than four people. We had our adult children with us. Only one bathroom is just inconvenient- not a deal breaker. But having literally no place for four people to share a meal was very annoying unless you eat out every meal. "
Cozy Home Sweet Homewood.

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

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

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

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

9.4 out of 10, Exceptional, (3)
"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

10.0 out of 10, Exceptional, (15)
"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

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (44)
"In town for daughters wedding. We came from Texas. Property very easy to find. Had friends and family from Texas and Illinois. Couldn't have asked for a more perfect spot for wedding and reception location. Place was more than we could have asked for. Very clean. Fenced in back yard was more than perfect for the little mutt. Highly recommend for any occasion. James the Host, was the best. Very professional and asked if we were OK and if we needed anything. The only downfall, and that is on...
The price is AED 613
AED 1,328 total
includes taxes & fees
12 Jan - 13 Jan
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (16)
"Headed to Chicago for weekend getaway and stayed again at Larry's property. Our friends were impressed with the entire house and had such a great time. Kitchen and living room was perfect space for dinners and watching the games. The property again was immaculate, spotless and made us feel at home. Anytime we come to Chicago, will always look to stay here as it is our home away from home now!! ;-)"
Lux Home in Chicago 7mins Downtown

Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

9.4 out of 10, Exceptional, (10)
"The home is nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

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 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

2.0 star property
CentralChgo/2BR1Bath/PublTrans/Wifi/Garage/Laundry

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (1)
"Awesome stay!"
The price is AED 474
AED 1,165 total
includes taxes & fees
12 Jan - 13 Jan
Spacious 3br home near Chicago, fenced yard for pets

Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve

2.0 star property
9.8 out of 10, Exceptional, (10)
"Let me start off by saying, “The host ( Betty ) is totally awesome, very responsive and communicative.”This place is a hidden gem . Very clean and well maintained. We absolutely had no problems with this place . I contacted Betty and told her my son wanted to join us for our stay since he’s in Cincinnati OH and she totally understood and agreed he could stay . Wait , she did something special and said no extra charge, which we were willing to pay . I can’t thank her enough for making this...
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve

Secluded Crown Point Haven Near Golfing & Parks!

2.0 star property
Secluded Crown Point Haven Near Golfing & Parks!

Chic Chicago Retreat 2 Bedroom Home by RedAwning

3.0 star property
Chic Chicago Retreat 2 Bedroom Home by RedAwning

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

cozy home in Bridgeport Chicago. walking to park and river front

10.0 out of 10, Exceptional, (4)
"Good location easy communication"
cozy home in Bridgeport Chicago. walking to park and river front
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.

9.8 out of 10, Exceptional, (17)
"For the most part this was a great place to stay. If you want to be in the south suburbs this is ideal for getting to other places in other burbs or to the city. Our only caveat would be it should be emphasized that this is a much better property for two rather than four people. We had our adult children with us. Only one bathroom is just inconvenient- not a deal breaker. But having literally no place for four people to share a meal was very annoying unless you eat out every meal. "
Cozy Home Sweet Homewood.

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

9.8 out of 10, Exceptional, (7)
"Clean & Convenient "
Cozy & Lavish 2B/1B in Homewood! 5 min from Shopping, Expressway, & New Casino!!

Charming Home with Hot Tub and Private Yard. RELAX and be at PEACE

9.6 out of 10, Exceptional, (9)
"House was perfect for myself and coworker for the fabtech event fully stocked kitchen was nice for cooking then hot tub just topped the cake. Very clean place!"
Charming Home with Hot Tub and Private Yard. RELAX and be at PEACE
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.