Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)

Crestwood Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Crestwood vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,196 reviews)
"Great location"
United States
JAVIER
The price is AED 609
AED 822 total
includes taxes & fees
1 Jul - 2 Jul
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (798 reviews)
"Great place to stay."
United States
Benedictine
The price is AED 2,535
AED 3,192 total
includes taxes & fees
24 Jun - 25 Jun
Kasa Magnificent Mile Chicago
Desk, iron/ironing board, travel crib, WiFi

Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
The price is AED 444
AED 850 total
includes taxes & fees
6 Jul - 7 Jul
Gold Coast Hideaway | Vintage & Inviting Studio
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AED 973
AED 2,199 total
includes taxes & fees
28 Jun - 29 Jun
River North Rooftop With In and Out Parking 3
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is AED 613
AED 811 total
includes taxes & fees
28 Jun - 29 Jun
LIVN Millennium Park Downtown Chicago 1 BR
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (7 reviews)
"The parking situation is pretty rough. You have to park a half a mile away from the property. The room looks very luxurious in the pictures. However, once you get there, it does show some age and you can hear the other guest from above and below at all night not to mention that the city sounds are in full effect horns and traffic all night long and it’s difficult to get the room dark"
United States
Robert
LIVN West Loop Chicago 2 BR City View
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
"Great place to stay for our girls weekend. Very convenient to everything in the city! We had the second unit and just to know this is a walk up with about 40-45 stairs to get to the unit. "
United States
Dawn P.
Beautiful Unit CHI in Prime River North - 2
Interior

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (30 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
The price is AED 305
AED 424 total
includes taxes & fees
28 Jun - 29 Jun
Beautiful Rustic Cabin for Two!
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very Good, (3 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AED 683
AED 1,207 total
includes taxes & fees
2 Jul - 3 Jul
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is AED 646
AED 1,159 total
includes taxes & fees
1 Jul - 2 Jul
Chicago-Themed 1BR in a Central Spot near Downtown
Studio | Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (23 reviews)
"Great area and surprisingly nice room!"
United States
Michael
The price is AED 446
AED 1,122 total
includes taxes & fees
24 Jun - 25 Jun
Ground Floor Studios in Chicago by 747 Lofts
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
Kasa River North Chicago
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AED 489
AED 938 total
includes taxes & fees
30 Jun - 1 Jul
1BR Modern Luxe Apt with In-Unit Laundry
Interior

870 1&2 - 2 Separate Suites in same building

870 1&2 - 2 Separate Suites in same building
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great spot in a great area"
United States
Jesse H.
870 1&2 - 2 Separate Suites in same building
Interior

9 Mi to Downtown! Pet-Friendly Unit Near UChicago

9 Mi to Downtown! Pet-Friendly Unit Near UChicago
Woodlawn
10.0 out of 10, Exceptional, (2 reviews)
"Great host very accommodating."
United States
Kali P.
9 Mi to Downtown! Pet-Friendly Unit Near UChicago
TV, offices

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Perfect Stay!"
United States
Miyauna G.
The price is AED 1,168
AED 2,511 total
includes taxes & fees
19 Jul - 20 Jul
Downtown Chicago Stay with Free In & Out Parking 3
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
Modern West Loop Gem-City Views & Prime Location 4
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is AED 569
AED 1,023 total
includes taxes & fees
21 Jul - 22 Jul
Chic Studio in the Heart of the Gold Coast
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 1

Beautiful Unit CHI in Prime River North - 1
Downtown Chicago
9.2 out of 10, Wonderful, (21 reviews)
"Location was fun"
United States
Robert L.
Beautiful Unit CHI in Prime River North - 1
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"We stay here often. Love this place"
MICHELLE L 2-night trip
Posted less than an hour ago
Crowne Plaza Chicago West Loop by IHG

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Crestwood vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Crestwood?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Crestwood stay.

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 Oak Hill Park. 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.