Crestwood Holiday Rentals

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Our top choices for Crestwood holiday rentals

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 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
Tyler B.
The price is AU$340
includes taxes & fees
7 Apr - 8 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space

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, (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
Jennifer M.
The price is AU$652
includes taxes & fees
14 Apr - 15 Apr
River North Rooftop With In and Out Parking 3

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is AU$256
includes taxes & fees
12 Apr - 13 Apr
Modern Comfort: 1BR Unit w/ Laundry

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,120 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is AU$243
includes taxes & fees
5 Apr - 6 Apr
Sentral Michigan Avenue

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$310
includes taxes & fees
27 Apr - 28 Apr
Chic Studio in the Heart of the Gold Coast

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 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
2k G.
The price is AU$337
includes taxes & fees
5 Apr - 6 Apr
West Loop Living – Bright 1BR

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 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
Daysha
The price is AU$352
includes taxes & fees
5 Apr - 6 Apr
Kasa River North Chicago

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$337
includes taxes & fees
5 Apr - 6 Apr
1BR Modern Luxe Apt with In-Unit Laundry

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is AU$617
includes taxes & fees
15 Apr - 16 Apr
Premium Urban 4BR - Perfect Mix of Comfort & Location

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 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
Tina Y.
The price is AU$782
includes taxes & fees
22 Apr - 23 Apr
Modern West Loop Gem-City Views & Prime Location 3

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
The price is AU$213
includes taxes & fees
8 Apr - 9 Apr
LIVN Millennium Park Downtown Chicago Studio

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 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
Michelle R.
The price is AU$269
includes taxes & fees
9 Apr - 10 Apr
LIVN West Loop Chicago Queen Superior Studio

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (456 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is AU$382
includes taxes & fees
5 Apr - 6 Apr
Level Chicago – Old Town

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
The price is AU$338
includes taxes & fees
7 Apr - 8 Apr
Chicago-Themed 1BR in a Central Spot near Downtown

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (12 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is AU$662
includes taxes & fees
26 Apr - 27 Apr
Spacious 4BR Central Apartment w/ Skyline Views

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
9.0 out of 10, Wonderful, (21 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
The price is AU$169
includes taxes & fees
6 Apr - 7 Apr
Beautiful Rustic Cabin for Two!

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

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Gary
8.0 out of 10, Very good, (20 reviews)
"We love it "
United States
sergio o.
The price is AU$631
includes taxes & fees
6 Apr - 7 Apr
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

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

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (58 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is AU$486
includes taxes & fees
9 Apr - 10 Apr
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

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

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
The price is AU$262
includes taxes & fees
6 Apr - 7 Apr
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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

Find out more about Crestwood

Everything you need to know about Crestwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Crestwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Crestwood holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crestwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Crestwood holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Crestwood rentals

At Expedia, we put the best Crestwood holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Crestwood?

Yes, there are holiday rentals in Crestwood close to Hollywood Park, or you can select a more secluded 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 holiday rentals that Crestwood has to offer?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Crestwood is located in the city centre, and has a balcony, an arcade/games room and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Crestwood?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Soldier Field and Trinity Christian College.

What are holiday rentals like in Crestwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Crestwood. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.