Crestwood Vacation Rentals

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Jan 23 - Jan 25

Vacation Rentals in Crestwood

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (944)
"Near everything great amenities "
$220 nightly
The price is $258
Oct 5 - Oct 6
Total with taxes and fees
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (539)
"Very great place to stay!"
$200 nightly
The price is $235
Oct 6 - Oct 7
Total with taxes and fees
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (360)
"Great place to stay. Loved it!"
$278 nightly
The price is $327
Oct 19 - Oct 20
Total with taxes and fees
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (372)
"Great stay!"
$129 nightly
The price is $151
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (235)
"Great location and lovely amenities. "
$159 nightly
The price is $187
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (355)
"nice area, shops nearby"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (670)
"great room, clean good space and close to places "
$139 nightly
The price is $163
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (206)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (52)
"Place was in a great location close to good restaurants "
$139 nightly
The price is $163
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
$291 nightly
The price is $342
Oct 5 - Oct 6
Total with taxes and fees
Kasa River North Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (180)
"Great location!!!"
$186 nightly
The price is $219
Oct 22 - Oct 23
Total with taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (62)
"Good "
$79 nightly
The price is $89
Oct 5 - Oct 6
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Stylish Apartment near Chicago Downtown
Classic Apartment | Private kitchen

Stylish Apartment near Chicago Downtown

2.0 star property
$214 nightly
The price is $252
Oct 2 - Oct 3
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.6 out of 10, Good, (139)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
$192 nightly
The price is $214
Oct 15 - Oct 16
Total with taxes and fees
Stylish 1BR in West Loop
Cozy Studio in Hyde Park-Walk to Lake & University
Microwave, oven, stovetop, coffee/tea maker

Cozy Studio in Hyde Park-Walk to Lake & University

9.0 out of 10, Wonderful, (6)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
$159 nightly
The price is $177
Oct 2 - Oct 3
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University
Twice as Nice: Chic 2BR Stay with Style & Space
Interior

Twice as Nice: Chic 2BR Stay with Style & Space

9.4 out of 10, Exceptional, (8)
"Had a very nice time in Chicago!"
$236 nightly
The price is $264
Oct 29 - Oct 30
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (64)
"loved our stay there. close to UIC and Greektown. will stay again"
$189 nightly
The price is $222
Oct 5 - Oct 6
Total with taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
$200 nightly
The price is $235
Oct 2 - Oct 3
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Great Experience! "
Carlos 2-night trip
Posted 3 hours ago
Freehand Chicago

Find out more about Crestwood

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 $89 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

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?

2BR Traveler`s Favorite • Modern and Clean: Visitors like this Crestwood vacation home rental. It offers a garden, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Trinity Christian College.

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.