Crestwood Vacation Rentals

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Vacation Rentals in Crestwood

Our top choices for Crestwood vacation rentals

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (884)
"great food spots all around and beautiful sites to see "
$169 nightly
The price is $198
Sep 2 - Sep 3
Total includes taxes and fees
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (475)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (344)
"Great stay!"
$127 nightly
The price is $149
Sep 3 - Sep 4
Total includes taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (341)
"A lot of good food options walkable distance. "
$218 nightly
The price is $256
Sep 3 - Sep 4
Total includes taxes and fees
Level Chicago – Old Town

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (191)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (619)
"Nice view, and walkable area."
$110 nightly
The price is $129
Sep 3 - Sep 4
Total includes taxes and fees
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, (207)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
$161 nightly
The price is $189
Sep 14 - Sep 15
Total includes taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (175)
"Great location!!!"
$135 nightly
The price is $159
Sep 3 - Sep 4
Total includes taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (47)
"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."
$135 nightly
The price is $159
Sep 3 - Sep 4
Total includes taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (163)
"Great location and very clean! Will definitely be staying again. "
$206 nightly
The price is $242
Aug 25 - Aug 26
Total includes taxes and fees
Kasa River North Chicago

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

2.5 star property
3.6 out of 10, (51)
"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. "
$94 nightly
The price is $106
Aug 21 - Aug 22
Total includes taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
$168 nightly
The price is $197
Sep 2 - Sep 3
Total includes taxes and fees
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
$680 nightly
The price is $852
Aug 25 - Aug 26
Total includes taxes and fees
Art Villa

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
$173 nightly
The price is $194
Sep 2 - Sep 3
Total includes taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"Great location, easy stay!"
$212 nightly
The price is $248
Sep 4 - Sep 5
Total includes taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments

Bright & Roomy 4BR in Pilsen

7.8 out of 10, Good, (7)
$368 nightly
The price is $400
Aug 21 - Aug 22
Total includes taxes and fees
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."
$228 nightly
The price is $253
Sep 1 - Sep 2
Total includes taxes and fees
Your Perfect 2BR Home w/ Parking

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!
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 offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. 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.