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 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
The price is ￥22,640
￥26,576 total
includes taxes & fees
Nov 9 - Nov 10
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, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ￥28,296
￥41,545 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is ￥61,659
￥75,096 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is ￥13,280
￥38,339 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is ￥40,730
￥51,713 total
includes taxes & fees
Nov 1 - Nov 2
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.
The price is ￥17,502
￥47,367 total
includes taxes & fees
Oct 27 - Oct 28
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
The price is ￥10,909
￥26,167 total
includes taxes & fees
Oct 27 - Oct 28
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.
The price is ￥17,073
￥37,374 total
includes taxes & fees
Nov 3 - Nov 4
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.
The price is ￥22,621
￥32,950 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥32,580
￥83,052 total
includes taxes & fees
Oct 26 - Oct 27
5-minute walk to the largest old school arcade in America! Family friendly.
A modern office space with a wooden desk, a grey office chair, a potted plant, and a wall-mounted lamp.

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.
The price is ￥38,727
￥116,071 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is ￥33,666
￥56,094 total
includes taxes & fees
Oct 28 - Oct 29
At Home in Oak Park
Kitchen

13. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
The price is ￥11,383
￥37,768 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is ￥17,391
￥39,870 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is ￥32,869
￥73,050 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is ￥15,810
￥37,821 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is ￥15,225
￥37,340 total
includes taxes & fees
Oct 26 - Oct 27
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.
The price is ￥20,906
￥42,808 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is ￥38,260
￥51,359 total
includes taxes & fees
Oct 23 - Oct 24
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.
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

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Stayed 4 nights at this hotel during our visit in Chicago. I have traveled a decent bit and this is one of the best hotels I have stayed in. The hotel was updated and very clean. Customer service from all of the staff was excellent. The room had a great view and nice window bench. Very close to the riverwalk and centrally located to most things. Would definitely stay here again!"
Jay 4-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

Find out more about Crestwood

Search for holiday rentals in Crestwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Crestwood using one of the methods below:

  • View our selection of featured holiday rentals in Crestwood
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Look no further and take a look at our great range of rental properties in Crestwood!

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.