Crestwood Vacation Rentals

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Check prices for these dates

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Jul 28 - Jul 29
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Aug 8 - Aug 10

Vacation Rentals in Crestwood

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (845)
"We would stay here again. Very happy with our stay "
The price is P10,149
P13,591 total
includes taxes & fees
Aug 4 - Aug 5
Sentral Michigan Avenue
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (335)
"The property canceled on us 4 hours prior to check in"
The price is P7,236
P8,494 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (331)
"Hotel was nice"
The price is P14,872
P18,734 total
includes taxes & fees
Aug 27 - Aug 28
Level Chicago – Old Town
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (453)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (592)
"I would stay again. "
The price is P8,602
P10,098 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
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (124)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P7,485
P8,786 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (322)
"I definitely enjoyed my stay and roof deck was the highlight. "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (199)
"Clean, new, spacious "
The price is P12,539
P14,720 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (181)
"Great suite"
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

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 P9,178
P10,774 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
1 bedroom, desk, laptop workspace, blackout drapes

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 P4,833
P5,461 total
includes taxes & fees
Jul 30 - Jul 31
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (157)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

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 P8,158
P9,577 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy Greektown Apartments
Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is P12,102
P14,206 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

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 P5,133
P9,971 total
includes taxes & fees
Aug 12 - Aug 13
Ground Floor Studios in Chicago by 747 Lofts
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town for a concert there. There are walkable restaurants and parks nearby. We did not feel unsafe in the area. "
Lisamar 3-night trip
Posted 3 hours ago
Congress Plaza Hotel

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 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.