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

Crestwood Vacation Rentals

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 modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,374 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

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (69 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
$225 nightly
The price is $259
Nov 1 - Nov 2
Total with taxes and fees
Kasa Lake Shore Chicago
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
$444 nightly
The price is $475
Oct 19 - Oct 20
Total with taxes and fees
Romantic Escape - Adult Playhouse with Exotic Dungeon
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

4. 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.
$217 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
A modern kitchen with a large island, bar stools, and a city view.

5. 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
$317 nightly
The price is $372
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

6. 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.
$259 nightly
The price is $297
Oct 26 - Oct 27
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern kitchen with a stainless steel refrigerator, a stove, and white cabinets.

7. 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
$147 nightly
The price is $163
Oct 27 - Oct 28
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A living room with a grey sofa, a white coffee table, and a grey rug.

8. 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.
$218 nightly
The price is $233
Oct 29 - Oct 30
Total with taxes and fees
Small hidden Gem. Location!
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)
"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 modern kitchen with dark cabinets, stainless steel appliances, and a patterned tile backsplash.

10. 5-minute walk to the largest old school arcade in America! Family friendly.

5-minute walk to the largest old school arcade in America! Family friendly.
Brookfield
8.6 out of 10, Excellent, (9 reviews)
"A nice house that easily slept 4 kids and 4 adults. There were ants in the house, then than that it was very nice, it was easy to get to the train into Chicago from here."
United States
Ryan S.
$489 nightly
The price is $523
Oct 19 - Oct 20
Total with taxes and fees
5-minute walk to the largest old school arcade in America! Family friendly.
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

11. 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
Terrace/patio

12. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"The apartment was clean and had everything we needed for a comfortable stay. Highly recommended!"
Italy
Marco
$310 nightly
The price is $355
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
Kitchen

13. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
$219 nightly
The price is $238
Nov 15 - Nov 16
Total with taxes and fees
1BR in Prime Hyde Park Apartment
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

14. 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
$229 nightly
The price is $255
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

15. 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.
$432 nightly
The price is $462
Oct 20 - Oct 21
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
A kitchen with a stainless steel stove, oven, and microwave, with a clock on the wall.

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

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
$215 nightly
The price is $238
Oct 20 - Oct 21
Total with taxes and fees
Bright & Spacious 2BR– Prime Hyde Park Location
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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, (73 reviews)
"Easy access to the Green Line."
United States
Michael
$206 nightly
The price is $236
Oct 26 - Oct 27
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free 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)
"Adorable place to stay, decor is done so cute. Very comfortable family room to relax"
United States
Teresa S.
$256 nightly
The price is $271
Oct 19 - Oct 20
Total with taxes and fees
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
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.

19. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (26 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
$278 nightly
The price is $328
Oct 23 - Oct 24
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

20. 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.
$179 nightly
The price is $213
Oct 26 - Oct 27
Total with taxes and fees
Cozy Luxury 1BR - 10 Min to Downtown Chicago
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
"."
Moira 3-night trip
Posted 9 hours 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 $74 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.