Crestwood Holiday Rentals

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Holiday Rentals in Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (949)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is AU$315
includes taxes & fees
6 Oct - 7 Oct
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (548)
"Very great place to stay!"
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (361)
"Great place to stay. Loved it!"
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very good, (374)
"Great stay!"
The price is AU$225
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (235)
"Great location and lovely amenities. "
The price is AU$255
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (355)
"nice area, shops nearby"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (677)
"great room, clean good space and close to places "
The price is AU$270
includes taxes & fees
22 Oct - 23 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (207)
"This place was perfect "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
The price is AU$270
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
Kasa River North Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (181)
"Great location!!!"
The price is AU$255
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

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

3.0 star property
3.8 out of 10, (62)
"Good "
The price is AU$121
includes taxes & fees
6 Oct - 7 Oct
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Stylish Apartment near Chicago Downtown

2.0 star property
The price is AU$514
includes taxes & fees
6 Oct - 7 Oct
Stylish Apartment near Chicago Downtown

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.6 out of 10, Good, (140)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is AU$954
includes taxes & fees
15 Oct - 16 Oct
Art Villa

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is AU$310
includes taxes & fees
6 Oct - 7 Oct
Stylish 1BR in West Loop

Cozy Studio in Hyde Park-Walk to Lake & University

9.0 out of 10, Wonderful, (6)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is AU$302
includes taxes & fees
15 Oct - 16 Oct
Cozy Studio in Hyde Park-Walk to Lake & University

Twice as Nice: Chic 2BR Stay with Style & Space

9.4 out of 10, Exceptional, (9)
"Had a very nice time in Chicago!"
The price is AU$376
includes taxes & fees
3 Nov - 4 Nov
Twice as Nice: Chic 2BR Stay with Style & Space

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is AU$346
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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

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$121 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Crestwood offers a patio, a BBQ 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 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.