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Top Holiday Rentals in Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (801)
"Great stay!"
The price is £137
includes taxes & fees
2 Jul - 3 Jul
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (322)
"Hotel was nice"
The price is £325
includes taxes & fees
3 Jul - 4 Jul
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (311)
"Super cool spot in a great part of the city."
The price is £119
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (553)
"Great stay"
The price is £119
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (192)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is £195
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (430)
"We had an amazing week staying here. Highly recommend!!"
The price is £114
includes taxes & fees
2 Jul - 3 Jul
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very good, (108)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is £145
includes taxes & fees
7 Jul - 8 Jul
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (172)
"Great spot. "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is £119
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (40)
"Our stay was amazing. "
The price is £127
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (314)
"Great stay"
Kasa South Loop Chicago

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (152)
"Great stay, clean room!"
Kasa River North Chicago

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

2.5 star property
3.6 out of 10, (40)
"Nice inside room but it’s not safe outside area"
The price is £77
includes taxes & fees
8 Jul - 9 Jul
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is £187
includes taxes & fees
2 Jul - 3 Jul
Sonder by Marriott Bonvoy Greektown Apartments

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (121)
"Perfect for what we were looking for!"
Luxury Home Away From Your Home

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

2.0 star property
8.8 out of 10, Excellent, (6)
"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

LakeHouse

9.6 out of 10, Exceptional, (18)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

Spacious 3-bedroom apartment near downtown, FREE PARKING

10.0 out of 10, Exceptional, (1)
"Extremely clean space that was perfect for our group. We didn't spend a lot of time in the home during our stay, but when we did it was fantastic. Only minor gripe would be the upstairs neighbors, they were occasionally quite loud and woke us up a few times in the middle of the night. Would absolutely stay here again, if/when we come back to the area."
The price is £300
includes taxes & fees
8 Jul - 9 Jul
Spacious 3-bedroom apartment near downtown, FREE PARKING

Newly Revamped Home - For privacy lovers

Newly Revamped Home - For privacy lovers

Charming 3-bedroom house with WiFi in peaceful Hazel Crest

8.0 out of 10, Very good, (4)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is £315
includes taxes & fees
2 Jul - 3 Jul
Charming 3-bedroom house with WiFi in peaceful Hazel Crest
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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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 3-bedroom house with WiFi in peaceful Hazel Crest: This holiday home rental outside of Crestwood offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.