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

Crestwood Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Crestwood vacation rentals

A modern kitchen with stainless steel appliances, white cabinetry, and a granite countertop.

1. *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.
$389 nightly
The price is $415
Sep 8 - Sep 9
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
A living room with a blue sectional sofa, a glass coffee table, and yellow curtains.

2. 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.
$248 nightly
The price is $265
Sep 29 - Sep 30
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,296 reviews)
"A great place"
United States
Lahiru
$177 nightly
The price is $208
Sep 7 - Sep 8
Total with taxes and fees
Sentral Michigan Avenue
A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

4. 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.

5. 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
$236 nightly
The price is $281
Sep 7 - Sep 8
Total with taxes and fees
Kasa Lake Shore Chicago
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a gas stove.

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.
$375 nightly
The price is $417
Sep 29 - Sep 30
Total with taxes and fees
Charming & Cozy Getaway - A Heroic Stay Awaits!
A modern living room with a sofa, coffee table, and dining area. Large windows offer views of the cityscape.

7. Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.0 out of 10, Wonderful, (4 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
$605 nightly
The price is $676
Sep 28 - Sep 29
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 1
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

8. 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.
$327 nightly
The price is $368
Sep 7 - Sep 8
Total with taxes and fees
River North Private Balcony With In and Out Parking
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

9. 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.
$211 nightly
The price is $249
Sep 7 - Sep 8
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
A modern kitchen with a large island, bar stools, and a city view.

10. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
$308 nightly
The price is $361
Sep 7 - Sep 8
Total with taxes and fees
Level Chicago – Old Town
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

11. 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.
$227 nightly
The price is $255
Sep 7 - Sep 8
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

12. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.2 out of 10, Wonderful, (10 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
$191 nightly
The price is $226
Sep 7 - Sep 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Studio
A modern living room with a sectional sofa, a TV on a stand, a small dining area, and a door leading to another room.

13. 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 7 - Sep 8
Total with taxes and fees
Stylish 2BR Near Hyde Park, UChicago & Lake

14. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
9.4 out of 10, Exceptional, (6 reviews)
"Nice place, clean property, great views "
United States
Zach L.
$697 nightly
The price is $860
Sep 27 - Sep 28
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
A wooden deck with a railing, a staircase, and a window with a wreath.

15. 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 7 - Sep 8
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

16. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (27 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
$424 nightly
The price is $454
Sep 8 - Sep 9
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
A modern bedroom with a bed, a nightstand, a lamp, and artwork on the wall.

17. Wabash 4BR - Pool, Free In & Out Parking 2

Wabash 4BR - Pool, Free In & Out Parking 2
Downtown Chicago
$246 nightly
The price is $304
Sep 22 - Sep 23
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 2
A kitchen with white cabinets, a microwave, a kettle, and a toaster.

18. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
$390 nightly
The price is $436
Sep 8 - Sep 9
Total with taxes and fees
Plymouth Collection: 3BD 2BA High Floor with Gym

19. South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
$497 nightly
The price is $567
Sep 3 - Sep 4
Total with taxes and fees
South Loop Rooftop With In & Out Parking 1
A spacious lobby with leather sofas, a coffee table, and a TV screen.

20. Downtown Chicago Stay with Free In & Out Parking 6

Downtown Chicago Stay with Free In & Out Parking 6
Downtown Chicago
$433 nightly
The price is $488
Sep 9 - Sep 10
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crestwood Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Amazing hotel ! Was in the midst of everything and the staff was extremely helpful and even upgraded our room! Would definitely book again"
Dwayne 2-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

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 $72 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.