Search Vacation Homes in Flossmoor

Compare 164 Vacation Homes in Flossmoor 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
Staycation Retreat
Living area

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.
Living area

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
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
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

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
Game room

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
Room

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
1st Floor Living Room

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
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 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
Spacious 3br home near Chicago, fenced yard for pets
Exterior

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
Private kitchen

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

2.0 star property
9.8 out of 10, Exceptional, (10)
"Really enjoyed our short stay. Clean and very convenient. "
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
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!
Cheerful 4 bedroom smart home w/ indoor fireplace
Room

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, king and queen bed Indiana home!
Private kitchen

Cozy, king and queen bed Indiana home!

9.0 out of 10, Wonderful, (12)
"We all enjoyed our stay."
Cozy, king and queen bed Indiana home!
Spacious Family Glenwood Estates Home w/ Hot Tub!
Glenwood Vacation Rental | 4BR | 2.5BA | 2,442 Sq Ft | Step-Free Entry

Spacious Family Glenwood Estates Home w/ Hot Tub!

9.4 out of 10, Exceptional, (14)
"Place was perfect! I grew up in the suburbs of Chicago and wanted to come back to honor my grandmother's 90th birthday. This place was perfect. It had a piano and the pastor was able to serinate her in playing church hymnals. Of course, her famiy, fch family, family and friends were all able to show"
Spacious Family Glenwood Estates Home w/ Hot Tub!
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
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
Living area

Welcome to Boss Barbie’s Dreamhouse! Everything is pink.

9.8 out of 10, Exceptional, (7)
"It was everything we imagined it to be!!!"
Welcome to Boss Barbie’s Dreamhouse! Everything is pink.
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 Flossmoor

Cozy 2- bedroom w/ patio mins from Midway Airport
Living room

Cozy 2- bedroom w/ patio mins from Midway Airport

9.8 out of 10, Exceptional, (9)
"The owner definitely pays attention to details. It had towels laid out in these cute little baskets a well stocked kitchen in terms of tools and the decor was very charming. The only reason I didn't give 5 stars is because it is an older building so the water pressure in the shower was low, there's no dishwasher and it is a 2 flat and the upstairs unit controlled the heat and we were on the first floor."
Cozy 2- bedroom w/ patio mins from Midway Airport
LakeHouse
Game room

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
Room

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
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.