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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$189 nightly
The price is $202
Oct 20 - Oct 21
Total with taxes and fees
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

2. 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
$444 nightly
The price is $475
Oct 19 - Oct 20
Total with taxes and fees
Romantic Escape - Adult Playhouse with Exotic Dungeon
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, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
$143 nightly
The price is $168
Nov 9 - Nov 10
Total with taxes and fees
Sentral Michigan Avenue
Lake

4. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
$229 nightly
The price is $272
Nov 1 - Nov 2
Total with taxes and fees
Kasa Lake Shore Chicago
Game room

5. 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.
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
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
9.8 out of 10, Exceptional, (35 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
A modern kitchen with a large island, bar stools, and a city view.

7. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
$324 nightly
The price is $380
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
A modern kitchen with a stainless steel refrigerator, a stove, and white cabinets.

8. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
$146 nightly
The price is $162
Oct 27 - Oct 28
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

9. 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, (30 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
$435 nightly
The price is $465
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.

10. 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, (23 reviews)
"Parking was free and right out front. Great apartment and the host was great with accommodations."
United States
Travis C.
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
$262 nightly
The price is $300
Oct 26 - Oct 27
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A wooden deck with a railing, a staircase, and a window with a wreath.

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, (35 reviews)
"Highly recommend this property. It’s located on a quiet clean nice residential street. And the home itself is wonderful: good furnishings, comfortable, three good bedrooms, clean well appointed bathroom, great backyard. I’d stay here anytime I’m in the area."
United States
Ruth Ann G.
$186 nightly
The price is $208
Oct 19 - Oct 20
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A living room with a grey sofa, a white coffee table, and a grey rug.

13. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (25 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
$219 nightly
The price is $234
Nov 2 - Nov 3
Total with taxes and fees
Small hidden Gem. Location!
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
9.2 out of 10, Wonderful, (41 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

15. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
$222 nightly
The price is $246
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
Terrace/patio

16. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
$310 nightly
The price is $355
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

17. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
$661 nightly
The price is $734
Nov 2 - Nov 3
Total with taxes and fees
Vibrant House, Walk to Train, Game Room
A modern living room with a grey sofa, a coffee table, and a view of the outside through large windows.

18. Conveniently Situated 1BR Apartment

Conveniently Situated 1BR Apartment
Hyde Park
$245 nightly
The price is $268
Oct 26 - Oct 27
Total with taxes and fees
Conveniently Situated 1BR Apartment
A kitchen with a stainless steel stove, oven, and microwave, with a clock on the wall.

19. Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
$227 nightly
The price is $252
Oct 26 - Oct 27
Total with taxes and fees
Bright & Spacious 2BR– Prime Hyde Park Location
A modern kitchen with a large island, coffee maker, and a view of the city.

20. Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking

Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
Lower West Side
9.2 out of 10, Wonderful, (5 reviews)
"Incredible place. Awesome neighborhood. Easy access to the freeways. Great neighborhood with tons of great local dining."
United States
Chad
Skyline View Apt - 5 minutes to Downtown - Games + Arcades - Free Parking
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"Room was good … but there was really bad sewer smell in bathroom"
Gurpreet 3-night trip
Posted 4 hours 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 $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 Marquette 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.