Title: Crestwood Vacation Rentals from $168: Search Short-Term Rentals | Expedia.com

[Crestwood Travel Guide](https://expedia.com/Crestwood.dx6960)[Hotels in Crestwood](https://expedia.com/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Flights to Crestwood](https://expedia.com/Cheap-Flights-To-Crestwood.d6960.Travel-Guide-Flights)[Things to do in Crestwood](https://expedia.com/Things-To-Do-In-Crestwood.d6960.Travel-Guide-Activities)[Car Rentals in Crestwood](https://expedia.com/Car-Rentals-In-Crestwood.d6960.Car-Rental-Guide)[Crestwood Vacation Packages](https://expedia.com/Crestwood.d6960.Destination-Travel-Guides)

![Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6960&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6960&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6960&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=6960&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Crestwood vacation rentals

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/7d7ccc69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c6bb5c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a5975d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/93c17f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunlit 1BR Apartment | Warm & Welcoming Space

[](https://www.expedia.com/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(2 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyler B.

$209 nightly

$234 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/d8e9b0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/a410264a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/7004f6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515200/117515137/57a172f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 3

[](https://www.expedia.com/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(4 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer M.

$406 nightly

$454 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-3.h117515137.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/afe63d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/19144195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/143f3ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/8ec83200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Comfort: 1BR Unit w/ Laundry

[](https://www.expedia.com/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(16 reviews)

"Great host comfortable bed close to restaurants and parks"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alana C.

$159 nightly

$176 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 Bedroom | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/f6d9d5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area | 55-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.com/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,120 reviews)

"Clean spacious my go to vacation spot all year around "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

xavier

$143 nightly

$168 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/7a65e5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/df8744f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/b5bee4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/f0a938f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic Studio in the Heart of the Gold Coast

[](https://www.expedia.com/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5 reviews)

"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brianna K.

$187 nightly

$210 total

Apr 26 - Apr 27

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b10cb31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/4fcb7f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b56ca762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

[](https://www.expedia.com/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(8 reviews)

"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

2k G.

$207 nightly

$232 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Apartment, 1 King Bed with Sofa bed, Pool Access (Self Check-in with Virtual Front Desk) | Living area | 55-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/2969f0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/88e54d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.com/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(187 reviews)

"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daysha

$215 nightly

$252 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/e255803d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/96789a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/4b4ff505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131871/2e28ea21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Modern Luxe Apt with In-Unit Laundry

[](https://www.expedia.com/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

Downtown Chicago

8.0/10

Very Good

(2 reviews)

"Great experience for me and my wife I would definitely come back "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

ShowtimeFam1

$207 nightly

$232 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-1BR-Modern-Luxe-Apt-With-In-Unit-Laundry.h119131871.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/44e9262b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/7fa2461a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/c31d7881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/715d39bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Urban 4BR - Perfect Mix of Comfort & Location

[](https://www.expedia.com/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.Hotel-Information)

Near North Side

10/10

Exceptional

(1 review)

"Nice place, clean property, great views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Zach L.

$350 nightly

$432 total

Apr 15 - Apr 16

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/45434900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/023c5e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Interior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/4c7ea681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/dfb80f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak Park Loft

[](https://www.expedia.com/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Good location, nice neighborhood, restaurants close"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda

[](https://www.expedia.com/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/2a358f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/5d728599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/d57fef46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122190000/122181300/122181219/b807e2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern West Loop Gem-City Views & Prime Location 3

[](https://www.expedia.com/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-3.h122181219.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(5 reviews)

"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tina Y.

$503 nightly

$551 total

Apr 22 - Apr 23

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Modern-West-Loop-Gem-City-Views-Prime-Location-3.h122181219.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/4a7e4d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/8aadb592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/47aac1cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868501/aa139e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN Millennium Park Downtown Chicago Studio

[](https://www.expedia.com/Chicago-Hotels-LIVN-Millennium-Park-Downtown-Chicago-Studio.h126868501.Hotel-Information)

Downtown Chicago

$123 nightly

$146 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LIVN-Millennium-Park-Downtown-Chicago-Studio.h126868501.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/5893f531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/c185e671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/2caa1de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126870000/126868600/126868503/65038522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LIVN West Loop Chicago Queen Superior Studio

[](https://www.expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago-Queen-Superior-Studio.h126868503.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1 review)

"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle R.

$156 nightly

$184 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LIVN-West-Loop-Chicago-Queen-Superior-Studio.h126868503.Hotel-Information)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/4a3a770c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Twin Bed, City View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.com/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(456 reviews)

"Would definitely stay again. Everything was great!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

$226 nightly

$266 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/385925ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/13f4699d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/cce101c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124200000/124198600/124198522/74a8f435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago-Themed 1BR in a Central Spot near Downtown

[](https://www.expedia.com/Chicago-Hotels-Chicago-Themed-1BR-In-A-Central-Spot-Near-Downtown.h124198522.Hotel-Information)

Downtown Chicago

$206 nightly

$231 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Chicago-Themed-1BR-In-A-Central-Spot-Near-Downtown.h124198522.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/ce588c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/92c646c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/57cc1f8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117790000/117782400/117782327/13dc1926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4BR Central Apartment w/ Skyline Views

[](https://www.expedia.com/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.Hotel-Information)

Near North Side

10/10

Exceptional

(12 reviews)

"Great location, comfortable room, welcoming host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Treseanne A.

$376 nightly

$464 total

Apr 26 - Apr 27

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-4BR-Modern-Gem-Sleek.h117782327.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/01933d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/ee53c125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/4eee2579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821529/39ec5645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Rustic Cabin for Two!

[](https://www.expedia.com/Griffith-Hotels-Beautiful-Rustic-Cabin-For-Two.h111821529.Hotel-Information)

Griffith

9.0/10

Wonderful

(21 reviews)

"The cabin was cute and cozy and the host was very welcoming. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deric D.

$103 nightly

$115 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Griffith-Hotels-Beautiful-Rustic-Cabin-For-Two.h111821529.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/b52cb489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/6b612432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/b918da67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102520000/102515700/102515612/1f5f8b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

[](https://www.expedia.com/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.Hotel-Information)

Gary

8.0/10

Very Good

(20 reviews)

"We love it "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

sergio o.

$396 nightly

$444 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Gary-Hotels-Theater-RMKG-BdFam-Friendly-Home-NR-DunesBeach.h102515612.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/7b6dc406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/932d3e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/26045e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/5569ce20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*The Comfy King Ranch\*King Bed Suite\*Fast Wi-Fi

[](https://www.expedia.com/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

Worth

9.4/10

Exceptional

(58 reviews)

"Home was exactly what we were needing fir our stay. Host was responsive and timely. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie H.

$310 nightly

$331 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e3fd1233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/e79449bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/da25d2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108220000/108219500/108219403/dfa31946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

[](https://www.expedia.com/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

Robertsdale

9.6/10

Exceptional

(24 reviews)

"I had a fun stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jusu K.

$160 nightly

$179 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Whiting-Hotels-Charming-3-BR-Home-On-A-Cobblestone-Street-Near-The-Lake-Michigan-Lakefront.h108219403.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-17&endDate=2026-04-18&regionId=6960&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Crestwood%2C+Illinois%2C+United+States+of+America&regionId=6960&latLong=41.661144%2C-87.752551&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Crestwood%2C+Illinois%2C+United+States+of+America&regionId=6960&latLong=41.661144%2C-87.752551&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Crestwood%2C+Illinois%2C+United+States+of+America&regionId=6960&latLong=41.661144%2C-87.752551&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Crestwood%2C+Illinois%2C+United+States+of+America&regionId=6960&latLong=41.661144%2C-87.752551&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Crestwood%2C+Illinois%2C+United+States+of+America&regionId=6960&latLong=41.661144%2C-87.752551&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Crestwood%2C+Illinois%2C+United+States+of+America&regionId=6960&latLong=41.661144%2C-87.752551&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=COTTAGE)

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## Top Crestwood Hotel Reviews

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Stayed here several times. This is the only place I stay in Chicago and always a five star experience!"

[](https://expedia.com/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

8/10 Good

"It was a very nice, clean property. Room was spotless and stayover service did an awesome job - making the beds and even setting up my children's pillows/"stuffies" nicely on the bed. I would rate it a 5 for service and based on what they have. I rated it an overall 4 because the indoor pool was quite small for the size of the property (about 300 rooms) and the demographic it serves (suites for families - though, I'm sure they get a lot of business travelers). The gym was pretty nice, but, again, it was on the smaller side considering the size of the property. This criticism is more for the basic build of the property which may have been out of the control of the ownership based on design and restrictions they faced with financial backing or the brand itself. I would stay again. It was a great location and an overall nice operation."

[](https://expedia.com/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg)

### Hotel Felix River North/Magnificent Mile

8/10 Good

"It is in a good location not far from public transit and the magnificent. The coffee in the morning is very good."

[](https://expedia.com/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"Emaculate"

[](https://expedia.com/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Nice staff "

[](https://expedia.com/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![The Chicago Hotel Collection Ambassador Gold Coast](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475_y.jpg)

### The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Great amount of space for a downtown hotel, however the room was showing its age with stained furniture, frayed couch covers, and cracks in the wall. Location was great and the bar and lobby are always beautiful. Overall we’d probably stay again but may start looking for other options if updates aren’t made."

[](https://expedia.com/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099_y.jpg)

### Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent

"Everybody was so helpful and accommodating. We were there for spring break.! Justin was so helpful and friendly, especially giving me advice about when to leave for the Chicago Bulls game. Ty guys"

[](https://expedia.com/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg)

### The Wade

8/10 Good

"Clean room, great view, close to lake! Loved! "

[](https://expedia.com/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg)

### River Hotel

10/10 Excellent

"Nice rooms and view of the river. Never stayed somewhere with a water refill station, which is super convenient. Most places give you a few complimentary bottles a day then make you pay for more. Love the variety of snacks that come in the room as well, and the packaging is great for safety. Placing a light switch and the thermostat by the bed is convenient. Great place."

[](https://expedia.com/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

## Find out more about Crestwood

**Everything you need to know about Crestwood vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Crestwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Crestwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Crestwood vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Crestwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Crestwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $168 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Crestwood rentals**

At Expedia, we put the best Crestwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Crestwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Crestwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crestwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Apartments in Crestwood ](https://expedia.com/Crestwood-Apartments.d6960-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Crestwood ](https://expedia.com/Crestwood-Private-Vacation-Homes.d6960-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Crestwood ](https://expedia.com/Crestwood-Condos.d6960-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Crestwood ](https://expedia.com/Crestwood-Apart-Hotels.d6960-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Crestwood ](https://expedia.com/Crestwood-Motels.d6960-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Crestwood ](https://expedia.com/Crestwood-Cottages.d6960-aaCottages.Travel-Guide-Accommodation)
- [B&B in Crestwood ](https://expedia.com/Crestwood-Bed-And-Breakfast.d6960-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Crestwood ](https://expedia.com/Crestwood-Guest-Houses.d6960-aaGuestHouses.Travel-Guide-Accommodation)
- [Hostels in Crestwood ](https://expedia.com/Crestwood-Hostels.d6960-aaHostels.Travel-Guide-Accommodation)
- [Resorts in Crestwood ](https://expedia.com/Crestwood-Resorts.d6960-aaResorts.Travel-Guide-Accommodation)
- [Houseboats in Crestwood ](https://expedia.com/Crestwood-Houseboats.d6960-aaHouseboats.Travel-Guide-Accommodation)
- [Cabin Rentals in Crestwood ](https://expedia.com/Crestwood-Cabins.d6960-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

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- [Hotel Rooms in Elmhurst](https://expedia.com/Elmhurst-Hotels.d7836.Travel-Guide-Hotels)
- [Hotel Rooms in Orland Park](https://expedia.com/Orland-Park-Hotels.d9270.Travel-Guide-Hotels)
- [Hotel Rooms in Oak Park](https://expedia.com/Oak-Park-Hotels.d9228.Travel-Guide-Hotels)

Cars

- [Car rentals in Naperville](https://expedia.com/Car-Rentals-In-Naperville.d9009.Car-Rental-Guide)
- [Car rentals in Des Plaines](https://expedia.com/Car-Rentals-In-Des-Plaines.d7863.Car-Rental-Guide)
- [Car rentals in Schaumburg](https://expedia.com/Car-Rentals-In-Schaumburg.d8107.Car-Rental-Guide)
- [Car rentals in Bolingbrook](https://expedia.com/Car-Rentals-In-Bolingbrook.d55064.Car-Rental-Guide)
- [Car rentals in Orland Park](https://expedia.com/Car-Rentals-In-Orland-Park.d9270.Car-Rental-Guide)

Activities

- [Things to do in Schaumburg](https://expedia.com/Things-To-Do-In-Schaumburg.d8107.Travel-Guide-Activities)