Crestwood Vacation Rentals

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Our top choices for Crestwood vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1036)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
$154 nightly
The price is $181
Jan 8 - Jan 9
Total with taxes and fees
Sentral Michigan Avenue

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
$218 nightly
The price is $256
Jan 8 - Jan 9
Total with taxes and fees
Kasa River North Chicago

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 8 - Jan 9
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"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
$149 nightly
The price is $166
Jan 8 - Jan 9
Total with taxes and fees
Gold Coast Living: Modern Studio Unit

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
$97 nightly
The price is $114
Jan 8 - Jan 9
Total with taxes and fees
Chicago luxury home suites

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

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (19)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$174 nightly
The price is $191
Jan 8 - Jan 9
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
Downtown Chicago
$153 nightly
The price is $168
Jan 13 - Jan 14
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.8 out of 10, Exceptional, (11)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$153 nightly
The price is $168
Jan 8 - Jan 9
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"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.
$153 nightly
The price is $168
Jan 8 - Jan 9
Total with taxes and fees
Sun-Drenched 1BR Apartment

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 11 - Jan 12
Total with taxes and fees
West Loop Living – Bright 1BR

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
$153 nightly
The price is $168
Jan 15 - Jan 16
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4)
"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.
$282 nightly
The price is $313
Jan 13 - Jan 14
Total with taxes and fees
River North Rooftop With In and Out Parking 3

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
$222 nightly
The price is $261
Jan 11 - Jan 12
Total with taxes and fees
Level Chicago – Old Town

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"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
$153 nightly
The price is $168
Jan 21 - Jan 22
Total with taxes and fees
Sleek 1BR Apt w/ Laundry

Vintage Studio in Chicago’s Gold Coast

Vintage Studio in Chicago’s Gold Coast
Downtown Chicago
$149 nightly
The price is $166
Jan 8 - Jan 9
Total with taxes and fees
Vintage Studio in Chicago’s Gold Coast

Contemporary 2BR Apartment in Vibrant Hyde Park

Contemporary 2BR Apartment in Vibrant Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (1)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
$163 nightly
The price is $178
Jan 11 - Jan 12
Total with taxes and fees
Contemporary 2BR Apartment in Vibrant Hyde Park

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
$153 nightly
The price is $168
Jan 8 - Jan 9
Total with taxes and fees
Stylish Gold Coast 1BR with Vintage Flair

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
$153 nightly
The price is $168
Jan 8 - Jan 9
Total with taxes and fees
Complete 1BR Home Sum

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
$137 nightly
The price is $151
Jan 11 - Jan 12
Total with taxes and fees
Studio Unit | Chic + Prime Location

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
$176 nightly
The price is $193
Jan 19 - Jan 20
Total with taxes and fees
Stylish Japanese-Themed 2BR Apt Close to Downtown
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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Crestwood vacation home rental. It offers a patio, a barbecue grill, 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.