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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Crestwood vacation rentals

A hotel room with a bed, a TV mounted on the wall, a desk with a chair, and a door.

1. 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
$183 nightly
The price is $195
Sep 29 - Sep 30
Total with taxes and fees
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.

2. Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.2 out of 10, Wonderful, (21 reviews)
"Great little place not far from downtown. Clean apartment and a comfortable bed. Daughter slept on the couch and said it wasn't too bad. Everything worked as expected with no issues. Can hear people walking up the steps from time to time but overall pretty quiet. Took some time to find a parking spot but not the host's fault. Overall a great experience and would stay again."
United States
Garrett C.
$158 nightly
The price is $169
Sep 30 - Oct 1
Total with taxes and fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

3. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
$484 nightly
The price is $518
Sep 24 - Sep 25
Total with taxes and fees
Romantic Escape - Adult Playhouse with Exotic Dungeon

4. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
$199 nightly
The price is $223
Sep 30 - Oct 1
Total with taxes and fees
Cozy Urban View Retreat Near Downtown - Sleeps 7
A modern building with the name 'SENIORAL' prominently displayed on the facade.

5. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,336 reviews)
"Great venue"
United States
Arthur Noel
$177 nightly
The price is $208
Sep 27 - Sep 28
Total with taxes and fees
Sentral Michigan Avenue
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

6. 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, (32 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.
$176 nightly
The price is $189
Oct 13 - Oct 14
Total with taxes and fees
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A modern living room with a sectional sofa, a TV on a stand, a small dining area, and a door leading to another room.

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

Stylish 2BR Near Hyde Park, UChicago & Lake
Woodlawn
10.0 out of 10, Exceptional, (7 reviews)
"Property looks recently renovated and has everything you need for a comfortable stay."
United States
Anna P.
$331 nightly
The price is $408
Sep 29 - Sep 30
Total with taxes and fees
Stylish 2BR Near Hyde Park, UChicago & Lake

8. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade

Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Brighton Park
9.4 out of 10, Exceptional, (13 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
$234 nightly
The price is $263
Sep 29 - Sep 30
Total with taxes and fees
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
A wooden deck with a railing, a staircase, and a window with a wreath.

9. 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, (35 reviews)
"I had a fun stay "
United States
Jusu K.
$186 nightly
The price is $208
Oct 4 - Oct 5
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

10. 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, (71 reviews)
"Easy access to the Green Line."
United States
Michael
$219 nightly
The price is $251
Sep 28 - Sep 29
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

11. 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, (28 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
$430 nightly
The price is $460
Oct 20 - Oct 21
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
A living room with a gray sofa, a coffee table, a TV mounted on the wall, and a wooden door.

12. Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Berwyn
9.8 out of 10, Exceptional, (22 reviews)
"Great place to stay "
United States
Harquesha S.
$168 nightly
The price is $179
Oct 6 - Oct 7
Total with taxes and fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A modern kitchen with white cabinets, a stainless steel refrigerator, a black stove, and a dining table with chairs.

13. Experience Forest Park living near Top Places like downtown Chicago

Experience Forest Park living near Top Places like downtown Chicago
Forest Park
9.4 out of 10, Exceptional, (18 reviews)
"Good location for visiting family just outside Chicago."
United States
Josh H.
$322 nightly
The price is $344
Sep 27 - Sep 28
Total with taxes and fees
Experience Forest Park living near Top Places like downtown Chicago
A living room with a brick fireplace, a flat-screen TV mounted above it, and a large potted plant.

14. 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, (40 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
$190 nightly
The price is $203
Oct 13 - Oct 14
Total with taxes and fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

15. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (80 reviews)
"Excellent place to stay!"
United States
Alicia K.
$263 nightly
The price is $301
Sep 28 - Sep 29
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

16. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
$281 nightly
The price is $300
Sep 28 - Sep 29
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

17. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
$204 nightly
The price is $216
Oct 4 - Oct 5
Total with taxes and fees
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern living room with a large white table, grey sofa, and a flat-screen TV mounted on the wall.

18. King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (10 reviews)
"We had a great stay. The host communicated well, property was clean, well stocked, and had plenty of space. If we were visiting this area again we would definitely stay here."
United States
Jennifer A.
$248 nightly
The price is $262
Sep 28 - Sep 29
Total with taxes and fees
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

19. Cozy Luxury 1BR - 10 Min to Downtown Chicago

Cozy Luxury 1BR - 10 Min to Downtown Chicago
Lawndale
7.8 out of 10, Good, (12 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.
$210 nightly
The price is $249
Oct 7 - Oct 8
Total with taxes and fees
Cozy Luxury 1BR - 10 Min to Downtown Chicago
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

20. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
$252 nightly
The price is $288
Oct 12 - Oct 13
Total with taxes and fees
A quiet stay while you are away
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Nice and clean"
Heather 1-night trip
Posted less than an hour ago
Hyatt Regency Chicago

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 $76 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 Centennial Park. 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.