Crestwood Holiday Rentals

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Holiday Rentals in Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (861)
"Great stay!"
The price is AU$352
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (339)
"The property canceled on us 4 hours prior to check in"
The price is AU$230
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (335)
"A lot of good food options walkable distance. "
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (460)
"Kasa apartments are two blocks away from Magnificent mile street. It is a really nice area and there are a lot of attractions close by. We had a wonderful time!!"
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (182)
"Definitely will back soon, very clean and spacious."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (605)
"I would stay again. "
The price is AU$259
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (325)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (127)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$276
includes taxes & fees
21 Aug - 22 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (201)
"Clean, new, spacious "
The price is AU$307
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (171)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is AU$276
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (159)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.6 out of 10, (50)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is AU$148
includes taxes & fees
22 Aug - 23 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (43)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is AU$245
includes taxes & fees
20 Aug - 21 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (58)
"Great location, easy stay!"
The price is AU$384
includes taxes & fees
19 Aug - 20 Aug
Sonder by Marriott Bonvoy Greektown Apartments

Bright & Roomy 4BR in Pilsen

7.8 out of 10, Good, (7)
The price is AU$632
includes taxes & fees
12 Aug - 13 Aug
Bright & Roomy 4BR in Pilsen

Your Perfect 2BR Home w/ Parking

8.0 out of 10, Very good, (4)
"Great location, close to United Center. Our host was super and was able to help me when I couldn't follow the instructions (lol). Wish I could have had a longer stay."
The price is AU$392
includes taxes & fees
2 Sept - 3 Sept
Your Perfect 2BR Home w/ Parking

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

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

Come experience The Lake Shore!

10.0 out of 10, Exceptional, (1)
"We had a great stay at the property. "
Come experience The Lake Shore!

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

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

6.0 out of 10, (3)
"Very nice place "
The price is AU$366
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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

Frequently asked questions

Can I find a holiday rental in Crestwood?

Yes, there are holiday rentals in Crestwood close to Hollywood Park, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Crestwood. Make sure you have time to check out the entertainment choices while you're in the area.

What are some of the best holiday rentals that Crestwood has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Crestwood is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Crestwood?

While exploring the area, visit family-friendly sights like Hollywood Park, or get outside and enjoy nature at Lake Katherine Nature Center. In the wider area, you’ll find Soldier Field and Trinity Christian College.

What are holiday rentals like in Crestwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Crestwood. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.