Crestwood Holiday Rentals from €163: Search Short-Term Rentals

Q: 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.

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Our top choices for Crestwood holiday rentals

Sentral Michigan Avenue

Downtown Chicago

xavier

includes taxes & fees

12 Apr - 13 Apr

LIVN Millennium Park Downtown Chicago Superior 1BR

Downtown Chicago

Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Michelle

includes taxes & fees

7 Apr - 8 Apr

Stylish Gold Coast 1BR with Vintage Flair

Downtown Chicago

includes taxes & fees

7 Apr - 8 Apr

Kasa River North Chicago

Downtown Chicago

Daysha

includes taxes & fees

22 Apr - 23 Apr

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

West Loop Living – Bright 1BR

Downtown Chicago

2k G.

includes taxes & fees

7 Apr - 8 Apr

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Downtown Chicago

includes taxes & fees

7 Apr - 8 Apr

LIVN West Loop Chicago 1 BR

Downtown Chicago

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Top Crestwood Hotel Reviews

Palmer House a Hilton Hotel

10/10 Excellent

"Clean room! Enjoyed the entertainment on Saturday evening! This property will definitely be my choice to stay the next time I’m in Chicago!"

Hilton Chicago

8/10 Good

"It's a really cool old building that has been updated to current standards and expectations. Everything was very clean. It was very expensive for parking, but it's downtown Chicago it's all pretty expensive. We didn't use the restaurants but there is a grab and go type place on the first floor that we used that was convenient. Just beware everything is 2-3 times higher price wise than in a store. "

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The walls were paper thin, and our neighbors partied in their room every night until about 1AM. we did call the front desk who called them and got them at least to turn off the music, but even their talking voices could be heard in the room. Its a beautiful hotel but I wasn't able to get much sleep so if you're in town for business I'd avoid this place"

DoubleTree by Hilton Chicago - Magnificent Mile

8/10 Good

"There are no domes when we went which attracted to this property. But otherwise very good cleanliness staff and help. We had our bath tub clogged but they gave us an hour extra for checkout.I do recommend this place if they really have the domes set up with heaters ."

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, apart-hotels, 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 favorite 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 depends 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 €163 per night. Entering your travel dates in the search wizard you might find 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.

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