Crestwood Holiday Rentals from €58: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Crestwood has to offer?

Luxury Home Away From Your Home : This holiday home rental outside of Crestwood is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Crestwood

"Excellent property. Everything was top notch. "

includes taxes & fees

15 Jan - 16 Jan

Superior Apartment, 1 Bedroom, Balcony, City View | Living area

"Great place to spend a few days. "

includes taxes & fees

30 Jan - 31 Jan

"Wonderful experience. Easy in and out access. Very comfortable "

includes taxes & fees

21 Jan - 22 Jan

49-inch Smart TV with digital channels, TV, streaming services

"Kasa was a pleasant surprise. Based on previous reviews, we understood that this was not a traditional hotel with amenities and had a virtual front desk but we did have an onsite person that did help us check in and store luggage. The apartment style room was very spacious and clean. We enjoyed having the extra space to spread out and the full kitchen was so handy when storing food or leftovers. Also, when we didn’t get utensils with our to go orders- Kasa had us covered. It was a nice home...

"It was quite nice overall! The only inconvenience to note was the parking situation close was not ideal and the fan didn’t work in the restroom"

includes taxes & fees

9 Feb - 10 Feb

"Besides hallways being loud and like frat house from 1 to 3am , the police showing up it was very great"

includes taxes & fees

26 Jan - 27 Jan

"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...

includes taxes & fees

6 Feb - 7 Feb

50-inch Smart TV with satellite channels

"Stayed here for a couple of nights while attending a trade show downtown. Very limited parking on the street so ended up parking in a garage near the hospital (about a 10 min walk away). Hotel was a little difficult to find as it is not highly visible from street. Rooms are excellent. Very clean, modern and spacious. This property does not use cards and communicates via text what your access code will be. I missed this (my fault) but it made for an interesting "check in" by not being able to get...

Free toiletries, hair dryer, towels, soap

"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."

includes taxes & fees

10 Feb - 11 Feb

42-inch Smart TV with digital channels, TV, streaming services

"It was great. Place was clean. Stocked with essentials. Great place to be. Would definitely stay here again"

"Great communication, very convenient and excellent property amenities. "

includes taxes & fees

20 Jan - 21 Jan

"Loved the location. "

includes taxes & fees

10 Feb - 11 Feb

"Our stay was amazing. "

includes taxes & fees

21 Jan - 22 Jan

"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"

40-inch flat-screen TV with digital channels, TV

"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "

includes taxes & fees

6 Feb - 7 Feb

"The host was very kind and welcoming! I had no issues with my stay. The parking for visitors is the only con but overall it was worked out with street parking. I would definitely book again and have already gave referrals! Great place for intimate gatherings!"

"Always enjoy kicking off our holidays and celebrating our anniversary at this beautiful penthouse. Well equipped and perfect location!"

"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."

"Our family had a very nice stay. Clean and comfortable. There are lots of great places to eat right outside your door. Excellent location for seeing Chicago."

"Overall for solo travel is recommended."

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Other types of properties in Crestwood you may be interested in

"Steve the door man and Johnny the security guard are the best ! Donavan is good also . We used a very nice car ( Lincoln Navigator ) that Steve got for us . "

includes taxes & fees

17 Jan - 18 Jan

"I really enjoyed my stay. The hotel was clean, and up to date. My room was kind of situated in a duck off location, which was private and quiet. The only thing that kind of made me feel uneasy was that there were no cameras in the hallway leading to my room. But overall everything went smooth. Valet was prompt. I also liked the hydration station they had on each floor, where you could get a water bottle and fill it up. I would stay again. "

includes taxes & fees

20 Jan - 21 Jan

"The room was very nice, the shower and the city view were amazing. "

includes taxes & fees

12 Feb - 13 Feb

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 €58 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.

Recent reviews of Crestwood properties

5/5 Excellent

"Good location"

A verified traveller from Philadelphia stayed at River Hotel

Posted 1 day ago

Embassy Suites by Hilton Chicago Downtown River North

5/5 Excellent

"The Embassy had everything that we needed and also offered additional services, that were unexpected! Our room was spacious, had a Fantastic view of the city, the staff was helpful and very nice, the Happy Hour was delightful, the washer and dryer was FREE and the valet parking was convenient and easily accessible!! We will DEFINITELY visit this location again, when we're in Chicago!"

A verified traveller stayed at Embassy Suites by Hilton Chicago Downtown River North

Posted 2 days ago

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?

Luxury Home Away From Your Home: This holiday home rental outside of Crestwood is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 Marquette Park. In the wider area, you’ll find Trinity Christian College and Gaelic Park.

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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Crestwood

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Crestwood

Sentral Michigan Avenue

Sentral Michigan Avenue

Sonder South Wabash

Sonder South Wabash

Sonder Market Hall

Sonder Market Hall

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

Sonder The Burnham Apartments

Sonder The Burnham Apartments

Level Chicago – Old Town

Level Chicago – Old Town

Found Chicago powered by Sonder

Found Chicago powered by Sonder

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

Sonder Jewelers Row

Sonder Jewelers Row

Kasa South Loop Chicago

Kasa South Loop Chicago

Kasa River North Chicago

Kasa River North Chicago

Sonder The Plymouth

Sonder The Plymouth

Sonder The Opal

Sonder The Opal

Luxury Home Away From Your Home

Luxury Home Away From Your Home

Sonder Greektown

Sonder Greektown

LakeHouse

LakeHouse

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Experience Chicago living near United Center

Experience Chicago living near United Center

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts

Other types of properties in Crestwood you may be interested in

Congress Plaza Hotel

Congress Plaza Hotel

River Hotel

River Hotel

Eurostars Magnificent Mile

Eurostars Magnificent Mile

Find out more about Crestwood

Find out more about Crestwood

Recent reviews of Crestwood properties

Recent reviews of Crestwood properties

River Hotel

Frequently asked questions