Crestwood Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Crestwood vacation rentals

TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
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.
$228 nightly
The price is $257
May 4 - May 5
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space
Interior

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, (5 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.
$406 nightly
The price is $454
Apr 29 - Apr 30
Total with taxes and fees
River North Rooftop With In and Out Parking 3
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
$215 nightly
The price is $241
Apr 28 - Apr 29
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,139 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
$157 nightly
The price is $185
Apr 27 - Apr 28
Total with taxes and fees
Sentral Michigan Avenue
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
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
$204 nightly
The price is $230
Apr 28 - Apr 29
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
Exterior

Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
Envitae Hotel, 4BR Modern Sleek Apartment
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$259 nightly
The price is $293
Apr 27 - Apr 28
Total with taxes and fees
West Loop Living – Bright 1BR
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
$239 nightly
The price is $270
Apr 27 - Apr 28
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
$346 nightly
The price is $427
Apr 27 - Apr 28
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
Room

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean and easy experience. Didn’t love the mattress but overall enjoyed all other aspects of our stay! Would stay again! "
United States
Natalie C.
$846 nightly
The price is $999
May 15 - May 16
Total with taxes and fees
LIVN West Loop Chicago King Studio
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (190 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
$230 nightly
The price is $270
Apr 30 - May 1
Total with taxes and fees
Kasa River North Chicago
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (15 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$330 nightly
The price is $408
Apr 26 - Apr 27
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
$428 nightly
The price is $481
Apr 28 - Apr 29
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 4
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (467 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
$195 nightly
The price is $228
Apr 26 - Apr 27
Total with taxes and fees
Level Chicago – Old Town
Fridge, microwave, oven, stovetop

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.6 out of 10, Exceptional, (8 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
$602 nightly
The price is $690
Apr 26 - Apr 27
Total with taxes and fees
River North Private Deck With In and Out Parking
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"It's a very comfortable house! Every thing you need was there. A very comfortable bed, a television that works. Everything you needed was there and Jay was very happy to get you set up. I will definitely come back again, hopefully when the weather is nicer! "
United States
Fred D.
A quiet stay while you are away
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
$571 nightly
The price is $634
May 20 - May 21
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
Living area

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
LIVN Millennium Park Downtown Chicago 2BR
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very Good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$271 nightly
The price is $307
Apr 27 - Apr 28
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Iron/ironing board, travel crib, WiFi, bed sheets

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (7 reviews)
"Room was clean, check in was easy, and the owner was very communicative."
United States
David
$150 nightly
The price is $167
Apr 27 - Apr 28
Total with taxes and fees
Cozy Charm Studio Apt in 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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"A great option to stay in the city! Nice hotel and friendly staff."
Nicole 3-night trip
Posted 1 hour ago
Fairmont Chicago at Millennium Park

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 $185 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: Visitors like this Crestwood vacation home rental. It is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 Centennial Park. 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.