Crestwood Vacation Rentals

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Vacation Rentals in Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (843)
"We would stay here again. Very happy with our stay "
The price is CA $242
CA $325 total
includes taxes & fees
Aug 25 - Aug 26
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (333)
"The property canceled on us 4 hours prior to check in"
The price is CA $174
CA $204 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (331)
"Hotel was nice"
The price is CA $355
CA $447 total
includes taxes & fees
Aug 26 - Aug 27
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (451)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (586)
"I would stay again. "
The price is CA $205
CA $241 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (122)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is CA $245
CA $288 total
includes taxes & fees
Jul 27 - Jul 28
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (321)
"I definitely enjoyed my stay and roof deck was the highlight. "
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (197)
"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 CA $290
CA $340 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (179)
"Building was quiet. Good nearby restaurants. "
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, (169)
"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 CA $220
CA $258 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

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

2.5 star property
3.6 out of 10, (48)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is CA $116
CA $131 total
includes taxes & fees
Jul 27 - Jul 28
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (156)
"Great location and very clean! Will definitely be staying again. "
The price is CA $264
CA $447 total
includes taxes & fees
Aug 14 - Aug 15
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is CA $196
CA $230 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is CA $301
CA $353 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy Greektown Apartments

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

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!

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

The price is CA $254
CA $364 total
includes taxes & fees
Jul 28 - Jul 29
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

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

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.2 out of 10, Wonderful, (15)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is CA $131
CA $250 total
includes taxes & fees
Aug 12 - Aug 13
Ground Floor Studios in Chicago by 747 Lofts

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
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 vacation rental in Crestwood?

Yes, there are vacation rentals in Crestwood close to Hollywood Park, or you can go with a more remote 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 vacation home rentals in Crestwood?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: You might want to consider this vacation home rental near Crestwood, which is equipped with a barbecue grill, 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 larger area, you’ll find Soldier Field and Trinity Christian College.

What are vacation rentals like in Crestwood?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Crestwood. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.