Crestwood Vacation Rentals from ￥31,504: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Crestwood?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony : Visitors like this Crestwood vacation home rental. It is located in the city center and has a balcony, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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Our top choices for Crestwood vacation rentals

Modern Comfort: 1BR Unit w/ Laundry

Downtown Chicago

Gina G.

￥28,437 total

includes taxes & fees

Apr 20 - Apr 21

Sunlit 1BR Apartment | Warm & Welcoming Space

Downtown Chicago

Tyler B.

￥37,112 total

includes taxes & fees

Apr 26 - Apr 27

River North Rooftop With In and Out Parking 3

Downtown Chicago

Jennifer M.

￥72,272 total

includes taxes & fees

Apr 29 - Apr 30

Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Downtown Chicago

Seynabou

￥33,419 total

includes taxes & fees

Apr 29 - Apr 30

1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

Downtown Chicago

2k G.

￥36,067 total

includes taxes & fees

Apr 20 - Apr 21

Sentral Michigan Avenue

Downtown Chicago

xavier

￥31,504 total

includes taxes & fees

Apr 26 - Apr 27

Envitae Hotel, 4BR Modern Sleek Apartment

Near North Side

￥77,952 total

includes taxes & fees

May 13 - May 14

Plymouth Studio Suite with Gym, Rooftop, and Lobby

Chicago

Chicago-Themed 1BR in a Central Spot near Downtown

Downtown Chicago

Melissa M.

￥39,110 total

includes taxes & fees

Apr 29 - Apr 30

Premium Urban 4BR - Perfect Mix of Comfort & Location

Near North Side

Zach L.

Kasa River North Chicago

Downtown Chicago

Katherine

￥44,960 total

includes taxes & fees

Apr 30 - May 1

Modern West Loop Gem-City Views & Prime Location 6

Downtown Chicago

Daniel L.

￥102,320 total

includes taxes & fees

Apr 19 - Apr 20

LIVN West Loop Chicago Queen Superior Studio

Downtown Chicago

Michelle R.

￥29,520 total

includes taxes & fees

Apr 19 - Apr 20

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago

Renae S.

￥76,594 total

includes taxes & fees

Apr 28 - Apr 29

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago

ShowtimeFam1

￥37,112 total

includes taxes & fees

Apr 19 - Apr 20

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Michelle

￥32,670 total

includes taxes & fees

Apr 19 - Apr 20

Spacious 4BR Central Apartment w/ Skyline Views

Near North Side

Treseanne A.

￥74,418 total

includes taxes & fees

Apr 26 - Apr 27

A quiet stay while you are away

Oak Park

Fred D.

￥37,706 total

includes taxes & fees

Apr 20 - Apr 21

Beautiful Rustic Cabin for Two!

Griffith

Deric D.

￥18,890 total

includes taxes & fees

May 5 - May 6

Iron/ironing board, travel crib, WiFi, bed sheets

Cozy Charm Studio Apt in Chicago

Hyde Park

David

￥29,826 total

includes taxes & fees

Apr 22 - Apr 23

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Top Crestwood Hotel Reviews

Hotel Riu Plaza Chicago

10/10 Excellent

"Amazing hotel overall from service to stay"

Embassy Suites by Hilton Chicago Downtown River North

6/10 Okay

"The room was clean, and the beds were comfortable. The four reasons we chose this hotel were the location, price, pool, and included breakfast. The price was reasonable for what we experienced. The breakfast has an omelet station, which was great! The rest of the food were just average. Some foods were cold or soggy. Nothing special. Our biggest issue (which was partly out of their control) was the pool. Our kids were so excited about the hotel so they could swim! Unfortunately, the pool was closed for most of the evening because another child had an "incident" in the pool. The staff did tell us we could go down the block to swim at the pool of another hotel. When we considered that option, it was further than we wanted to walk with pool stuff and the pool looked much smaller. We were originally told the pool is usually closed for about an hour in these situations. Not only was the pool not opened an hour later, it was not open 13 hours later when we went the next morning! They did open up shortly after we wanted to swim in the morning. We had to adjust the itinerary of our trip because of this. Again, we recognize some things are out of the control of the hotel, but it was nevertheless disappointing. "

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

2/10 Terrible

"Hotel was the worst Sonesta property ever!! The cold water in the bathroom and all sinks do not condition to the temperature selected, the front door of hotel room all look severely damaged, sheets were soiled , thank goodness for staff member “Tony” that personally came to change the sheets after checking in… the toilet seat is tiny also "

Aloft Chicago Mag Mile

6/10 Okay

"Clean and comfortable room, overall clean and well kept facility. Bar staff was entertaining. Easy check in and out. Central location with plenty of bars and restaurants around. The building is not sound-proof AT ALL. The room I was in had a door to the room next to it, and the people in that room had the TV on almost the entire night. You can hear every noise in the hallway. The doors slam very loudly. The housekeeping staff was extremely unaware that they were being so loud. I wasn’t able to join zoom meetings in the room due to the noise level, ended up going to a nearby coffee shop. People were up and down the hall til 2am the second night and you could hear every word they were saying. I am not one to complain, I understand everyone is paying to stay there - there is just no sound proofing at all inside the room. Maybe look into designated “quiet floors” or something for those needing to work, study or who have early mornings. And inform the staff, especially the housekeeping crew, how loud it is inside the rooms so they can be mindful - they may not realize it’s an issue. "

Find out more about Crestwood

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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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: Visitors like this Crestwood vacation home rental. It is located in the city center and has a balcony, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 Centennial 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.

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Check prices for these dates

Our top choices for Crestwood vacation rentals

Modern Comfort: 1BR Unit w/ Laundry

Sunlit 1BR Apartment | Warm & Welcoming Space

River North Rooftop With In and Out Parking 3

Chic Studio in the Heart of the Gold Coast

West Loop Living – Bright 1BR

Sentral Michigan Avenue

Envitae Hotel, 4BR Modern Sleek Apartment

Plymouth Studio Suite with Gym, Rooftop, and Lobby

Chicago-Themed 1BR in a Central Spot near Downtown

Premium Urban 4BR - Perfect Mix of Comfort & Location

Kasa River North Chicago

Modern West Loop Gem-City Views & Prime Location 6

LIVN West Loop Chicago Queen Superior Studio

Downtown Chicago Stay with Free In & Out Parking 4

1BR Modern Luxe Apt with In-Unit Laundry

Level Chicago – Old Town

Spacious 4BR Central Apartment w/ Skyline Views

A quiet stay while you are away

Beautiful Rustic Cabin for Two!

Cozy Charm Studio Apt in Chicago

Find vacation rentals that suit your style

Top Crestwood Hotel Reviews

Hotel Riu Plaza Chicago

Hilton Chicago

Congress Plaza Hotel

Embassy Suites by Hilton Chicago Downtown River North

River Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairmont Chicago at Millennium Park

Aloft Chicago Mag Mile

Freehand Chicago

Find out more about Crestwood

Frequently asked questions

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