Holiday Rentals in Crestwood

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (689)
"it was alright, $77 extra for parking, no breakfast included but it was like a little apartment. no fan for guests either. no phone for communication but u can text their number yet they take forever to respond. "
The price is €170
includes taxes & fees
9 Mar - 10 Mar
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (442)
"Amazing space - I'll be requesting the same one in the summer :) Spacious and clean! Absolutely loved the view of Willis Tower from our room. Excellent stay!"
The price is €102
includes taxes & fees
27 Mar - 28 Mar
Sonder South Wabash

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is €152
includes taxes & fees
5 Mar - 6 Mar
Found Chicago powered by Sonder

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (144)
"Beautiful apartment! Very quiet area "
The price is €141
includes taxes & fees
1 Apr - 2 Apr
Sonder The Burnham Apartments

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (367)
"Conveniently located, and an excellent option for a longer stay. "
Kasa Magnificent Mile Chicago

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (258)
"It was wonderful!"
The price is €126
includes taxes & fees
1 Apr - 2 Apr
Sonder Market Hall

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (289)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is €214
includes taxes & fees
9 Mar - 10 Mar
Level Chicago – Old Town

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.0 out of 10, (5)
"HVAC did not work, no microwave no refrigerator. Only one sheet on bed Had to provide a security deposit not mentioned on reservation did not provide breakfast broken glass door on side of hotel Very noisy "
The price is €101
includes taxes & fees
6 Mar - 7 Mar
Comfort Inn Chicago Wind Creek Casino

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (127)
"We had an overall wodnerful experience. We were celebrating a milestone birthday and was perfect for a group of 4! The room was beautiful and close to everything!! We will definitely come back. "
The price is €122
includes taxes & fees
6 Mar - 7 Mar
Kasa River North Chicago

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (262)
"realy great place and very close to everything"
Kasa South Loop Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (139)
"Loved it Had to leave early but loved "
The price is €115
includes taxes & fees
27 Mar - 28 Mar
Sonder Jewelers Row

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (134)
"The suite was amazing - the decor was beautiful and it was well equipped with everything I needed for a longer stay. The coffee machine and local freshly ground coffee was a nice touch. The bed was incredibly comfortable too. There were a few tiny issues with the room - the water pressure in the shower was really poor making hair washing feel like a chore and there were no tea spoons which made stirring coffee or eating a yogurt kind of comical. However, neither of these were deal breakers for...
The Neighborhood Hotel-Little Italy

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (92)
"This is the best Sonder property we've ever stayed at!! The location is perfect for Chicago. We had a few different questions during our stay and we always received immediate and thorough answers by using the chat button in the app. Would definitely stay here again!"
The price is €116
includes taxes & fees
1 Apr - 2 Apr
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (29)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is €132
includes taxes & fees
12 Mar - 13 Mar
Sonder The Opal

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (42)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is €142
includes taxes & fees
25 Mar - 26 Mar
Sonder Greektown

ART Downtn RoofDeck-Private Grg-3 bdrm HOME-EVTesla -Sleeps 10-Pets

10.0 out of 10, Exceptional, (1)
"My family and I had a wonderful weekend in Chicago, all thanks to your beautiful home. We comfortably slept four people and enjoyed the ample space. The house is filled with stunning natural light during the day, thanks to the full windows on the second floor and a skylight in the stairwell leading to the third floor. One of the features we loved the most was the parking and the use of the garage. The kitchen was easy to navigate, and we appreciated the selection of coffee available."
ART Downtn RoofDeck-Private Grg-3 bdrm HOME-EVTesla -Sleeps 10-Pets

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (155)
"We love this well stocked condo. The location, off street parking and amenities make it a great home away from home for us. "
NEW LUXURY CONDO WITH PATIO DECK

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (36)
"I texted the host a question and he almost immediately got back to me and talked me through the entire check-in process, and he didn’t hang up until he was sure we were able to get in! This was my first out-of-state trip with my boyfriend, so it was an enormous relief to have such a dedicated host to help us out! Additionally, the interior was tidy and very pleasantly decorated!"
Chic Suite/Mins to L Train /Laundry/Free Parking

Experience Chicago in Hip Logan Square

9.2 out of 10, Wonderful, (5)
"Very clean townhome with all the necessary amenities. Owner was quickly responsive to all communications. Relatively quiet neighborhood. Next door neighbor had a Halloween party on a Sunday night that lasted until 3am. Wasn’t horribly loud but could hear enough noise that I needed to use my noise canceling headphones to sleep. The other nights were very quiet and peaceful. Would stay there again in the future. "
Experience Chicago in Hip Logan Square

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (168)
"My friends and I have driven down to Chicago every year now for around 4 years and we've stayed at different places each time. This place was the best one we've stayed at yet! Highly stocked and well-organized kitchen as well. Would highly recommend."
NEW LUXURY PENTHOUSE CONDO
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.
Don't see what you're looking for?
See all available properties in Crestwood
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Crestwood you may be interested in

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8576)
"I always love this place. "
The price is €130
includes taxes & fees
9 Mar - 10 Mar
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3852)
"This hotel is beautiful. Staff were nice & friendly helped me check in & out at a promptly time. Many lounge area to relax at. Even have a coffee room. I would definitely recommend 10/10. I’m visiting Chicago in 3months & definitely will be staying here again !"
The price is €92
includes taxes & fees
23 Mar - 24 Mar
River Hotel

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1765)
"I appreciate this property for such a pleasant experience. Antonio the concierge greeted us with great customer service and giving us recommendations in town. I definitely recommend this location. "
The price is €184
includes taxes & fees
6 Mar - 7 Mar
L7 Chicago by LOTTE
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.

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?

ART Downtn RoofDeck-Private Grg-3 bdrm HOME-EVTesla -Sleeps 10-Pets: This holiday home rental outside of Crestwood is located in the city centre, and has a fireplace, a balcony and air conditioning 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.