Crestwood Vacation Rentals

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Our top choices for Crestwood vacation rentals

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$207 nightly
The price is $232
Mar 1 - Mar 2
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$319 nightly
The price is $359
Mar 1 - Mar 2
Total with taxes and fees
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

Sleek 1BR Apartment w/ In-unit Laundry
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$218 nightly
The price is $245
Mar 23 - Mar 24
Total with taxes and fees
Sleek 1BR Apartment w/ In-unit Laundry

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$203 nightly
The price is $227
Mar 8 - Mar 9
Total with taxes and fees
Sun-Drenched 1BR Apartment

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,095 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
$135 nightly
The price is $158
Mar 2 - Mar 3
Total with taxes and fees
Sentral Michigan Avenue

Apartment in Downtown Chicago

Chic Studio in the Heart of the Gold Coast
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$195 nightly
The price is $220
Mar 1 - Mar 2
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$207 nightly
The price is $232
Mar 1 - Mar 2
Total with taxes and fees
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$207 nightly
The price is $232
Mar 1 - Mar 2
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
$223 nightly
The price is $248
Mar 2 - Mar 3
Total with taxes and fees
Stylish Japanese-Themed 2BR Apt Close to Downtown
8.8 out of 10, Excellent, (20 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
$92 nightly
The price is $103
Feb 28 - Mar 1
Total with taxes and fees
Beautiful Rustic Cabin for Two!

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (433 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
$213 nightly
The price is $250
Mar 3 - Mar 4
Total with taxes and fees
Level Chicago – Old Town

Vacation Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
$193 nightly
The price is $221
Mar 2 - Mar 3
Total with taxes and fees
A quiet stay while you are away

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (184 reviews)
"Awesome stay "
United States
Sally
$234 nightly
The price is $275
Mar 8 - Mar 9
Total with taxes and fees
Kasa River North Chicago

Apartment in Oak Park

The Oak Park Loft
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$237 nightly
The price is $271
Mar 2 - Mar 3
Total with taxes and fees
The Oak Park Loft
9.4 out of 10, Exceptional, (57 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
$305 nightly
The price is $325
Mar 1 - Mar 2
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
$284 nightly
The price is $334
Mar 1 - Mar 2
Total with taxes and fees
River West, Second Floor Chicago by 747 Lofts
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
$197 nightly
The price is $221
Mar 12 - Mar 13
Total with taxes and fees
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
9.0 out of 10, Wonderful, (18 reviews)
"Really cute house! Very comfortable beds. Clean and well maintained. "
United States
Samantha D.
$291 nightly
The price is $311
Mar 1 - Mar 2
Total with taxes and fees
Spacious 3br home near Chicago, fenced yard for pets
9.6 out of 10, Exceptional, (31 reviews)
"Great option for a relatively affordable place to stay near family."
United States
Erick B.
$118 nightly
The price is $125
Mar 2 - Mar 3
Total with taxes and fees
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Apartment in Downtown Chicago

Complete 1BR Fully Furnished Home
$207 nightly
The price is $232
Mar 1 - Mar 2
Total with taxes and fees
Complete 1BR Fully Furnished Home
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

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 $106 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.

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?

A Home Away From Home!: Visitors like this Crestwood vacation home rental. It offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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 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.