A serene lake with reflections of trees and a cloudy sky.

Crestwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Crestwood vacation rentals

Living area

1. Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.2 out of 10, Wonderful, (11 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
$252 nightly
The price is $269
Sep 8 - Sep 9
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Room

2. Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Hickory Hills
9.6 out of 10, Exceptional, (8 reviews)
"Easy to locate shopping mall close by friendly neighborhood and safe. when you're looking at stay away from home that's where you want to be."
United States
Ralph
$185 nightly
The price is $197
Sep 9 - Sep 10
Total with taxes and fees
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
Private kitchen

3. *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, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
$399 nightly
The price is $426
Sep 2 - Sep 3
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Exterior

4. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,292 reviews)
"Nice stay"
United States
Heather
$177 nightly
The price is $208
Sep 1 - Sep 2
Total with taxes and fees
Sentral Michigan Avenue
Dining

5. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (31 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private kitchen

6. Charming & Cozy Getaway - A Heroic Stay Awaits!

Charming & Cozy Getaway - A Heroic Stay Awaits!
Homewood
10.0 out of 10, Exceptional, (20 reviews)
"We had such a lovely stay. It was cute, quaint, and the perfect place to spend Mother’s Day with my mother. The space was cozy, clean, and had such a peaceful charm to it. We truly enjoyed our time here and would absolutely stay again!"
United States
Nikki B.
$356 nightly
The price is $395
Sep 29 - Sep 30
Total with taxes and fees
Charming & Cozy Getaway - A Heroic Stay Awaits!
Living area

7. Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Lake

8. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (25 reviews)
"Great location and super clean!"
United States
Erica
$220 nightly
The price is $262
Sep 9 - Sep 10
Total with taxes and fees
Kasa Lake Shore Chicago
Interior

9. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.4 out of 10, Exceptional, (39 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
$185 nightly
The price is $197
Sep 1 - Sep 2
Total with taxes and fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Living area

10. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
$240 nightly
The price is $269
Sep 7 - Sep 8
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Room

11. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
$189 nightly
The price is $223
Sep 1 - Sep 2
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
Property grounds

12. 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
9.8 out of 10, Exceptional, (34 reviews)
"I had a fun stay "
United States
Jusu K.
$187 nightly
The price is $210
Sep 2 - Sep 3
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Living area

13. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
$334 nightly
The price is $377
Sep 7 - Sep 8
Total with taxes and fees
River North Private Balcony With In and Out Parking
Living area

14. Stylish 2BR Near Hyde Park, UChicago & Lake

Stylish 2BR Near Hyde Park, UChicago & Lake
Woodlawn
10.0 out of 10, Exceptional, (7 reviews)
"Definitely would rent again "
United States
Brittney J.
$335 nightly
The price is $413
Sep 1 - Sep 2
Total with taxes and fees
Stylish 2BR Near Hyde Park, UChicago & Lake
Interior

15. Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
9.6 out of 10, Exceptional, (8 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.
$625 nightly
The price is $701
Sep 2 - Sep 3
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
Living area

16. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
$181 nightly
The price is $214
Sep 1 - Sep 2
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
Living area

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (70 reviews)
"Easy access to the Green Line."
United States
Michael
$216 nightly
The price is $248
Sep 1 - Sep 2
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
Private kitchen

18. Luxurious, Cozy Beauty 10 min from Downtown Chicago

Luxurious, Cozy Beauty 10 min from Downtown Chicago
Lawndale
7.6 out of 10, Good, (11 reviews)
"Don't miss out on this spot!! It's truly a must & great location!!! I really enjoyed my time here for real"
United States
Alexis R.
$251 nightly
The price is $298
Sep 15 - Sep 16
Total with taxes and fees
Luxurious, Cozy Beauty 10 min from Downtown Chicago
Exterior

19. Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower

Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower
Joliet
10.0 out of 10, Exceptional, (3 reviews)
"Such a clean, quiet, comfortable, roomy place to stay. The host, Ben, is great. I will definitely try to stay here next time, provided it’s not already booked."
United States
Max L.
$146 nightly
The price is $154
Sep 30 - Oct 1
Total with taxes and fees
Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower
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

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"The room was perfect and the staff is so nice and helpful! The parking was pretty expensive but understandable. There is a chipotle connected which was perfect for when we wanted to grab a quick dinner! Last thing is that breakfast ended at 9 am which was quite early for us who had stayed out late so I wish it was until at least 10 am"
Janelle 2-night trip
Posted less than an hour ago
Hampton Inn Chicago Downtown/Magnificent Mile

Find out more about Crestwood

Everything you need to know about Crestwood vacation rentals

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

Crestwood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Crestwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $73 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Crestwood rentals

At Expedia, we put the best Crestwood vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Crestwood?

Yes, there are vacation rentals in Crestwood close to Hollywood Park, or you can go with a more remote 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 vacation home rentals in Crestwood?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Crestwood vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Crestwood?

With 3 Expedia vacation rentals, you're sure 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 Lake Katherine Nature Center. In the larger area, you’ll find Soldier Field and Gaelic Park.

What are vacation rentals like in Crestwood?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Crestwood. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.