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Vacation Homes in Crestwood

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

The price is SAR 699
SAR 1,001 total
includes taxes & fees
28 Jul - 29 Jul
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (13)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

10.0 out of 10, Exceptional, (12)
"Lots of good food and close to transit! Amazing little spot."
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (124)
"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "
Luxury Home Away From Your Home

South Shore Retreat 5 bedrooms/entertainment

8.0 out of 10, Very Good, (3)
"Three weeks later tries to say we didn't pay when we have emails/proof saying otherwise. We checked in at the time, and some guy just comes in the backdoor with towels. Upon checkout, says we didn't leave the key & they had to get a locksmith - we literally saw someone come in with a key (man with towels at check in). Scary neighborhood, misleading advertising, terrible communication. "
South Shore Retreat 5 bedrooms/entertainment

Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

6.6 out of 10, (7)
"The property itself was ver clean just an older house. Very clean! The neighborhood was a little questionable for families who have never travelex to that area from a rural area. The stay was good and worked for what we needed!"
The price is SAR 422
SAR 1,128 total
includes taxes & fees
28 Jul - 29 Jul
Charming and spacious 3-bedroom townhome with WiFi and amenities in Gary

Stylish 3bd w/ backyard patio mins from Downtown!

2.0 star property
8.8 out of 10, Excellent, (3)
"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "
Stylish 3bd w/ backyard patio mins from Downtown!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

8.0 out of 10, Very Good, (7)
"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

6.0 out of 10, (1)
"We had a couple of challenges but the host was very attentive. Plenty of room and property was clean. "
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

Charming 3-bedroom house with WiFi in peaceful Hazel Crest

6.8 out of 10, (6)
The price is SAR 732
SAR 1,463 total
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house with WiFi in peaceful Hazel Crest

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (5)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped

The Family Retreat, The Family Retreat Oasis

2.0 out of 10, (1)
The Family Retreat, The Family Retreat Oasis

4BR Home with Game Room: Chicago Leisure Escape

The price is SAR 595
SAR 2,050 total
includes taxes & fees
28 Jul - 29 Jul
4BR Home with Game Room: Chicago Leisure Escape

Spacious 5-bedroom house great for large groups

Spacious 5-bedroom house great for large groups

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (7)
"We got all the help and instructions needed to easily find this clean, well-supplied apartment with lovely outdoor space attached. And with the Pink Line just a few minutes walk and The Loop just 6 stops away, it was the perfect home base for getting to all that Chicago has to offer!"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (56)
"Super convenient for Old Town and train station, will stay there again."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (8)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Spacious 4BR Home. Your Cozy Home Away from Home

10.0 out of 10, Exceptional, (1)
"What a luxury to have a full-sized house in urban Chicago! Everyone was able to have their own bedroom and bathroom and there was a full kitchen, dining, and living space so no one ever felt cramped or crowded. Plus all of the beds were queen or king sized! We also had access to a private garage behind the house, so finding parking was never an issue! The communication with the host was stellar and any question or concern was handled promptly. Two things to note: there are tenants living in...
Spacious 4BR Home. Your Cozy Home Away from Home
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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Top Crestwood Hotel Reviews