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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Crestwood vacation rentals

TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$407 nightly
The price is $467
Jul 26 - Jul 27
Total with taxes and fees
River North Rooftop With In and Out Parking 1
Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,216 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
$168 nightly
The price is $197
Aug 17 - Aug 18
Total with taxes and fees
Sentral Michigan Avenue
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (13 reviews)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
$193 nightly
The price is $228
Jul 19 - Jul 20
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
$189 nightly
The price is $223
Jul 19 - Jul 20
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
Smart TV

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
$225 nightly
The price is $258
Jul 26 - Jul 27
Total with taxes and fees
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$697 nightly
The price is $790
Aug 10 - Aug 11
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
Private kitchen

Soothing 1 bedroom apartment with AC in charming Oak Lawn,

Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Oak Lawn
9.0 out of 10, Wonderful, (2 reviews)
"The host was very friendly and helpful. There was a massive storm before and the host accommodated us with everything we needed"
United States
Bailey H.
$159 nightly
The price is $170
Jul 21 - Jul 22
Total with taxes and fees
Soothing 1 bedroom apartment with AC in charming Oak Lawn,
Dining

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
8.8 out of 10, Excellent, (3 reviews)
"I called the host about the thermostat not working and he said he would get in touch with somebody, never heard back from him and the problem was never solved. There were two window air conditioning units that I cleaned the filters myself as they were not very efficient."
United States
Raymond
$305 nightly
The price is $377
Jul 19 - Jul 20
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
$354 nightly
The price is $378
Aug 10 - Aug 11
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Smart TV, fireplace, video games, DVD player

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.0 out of 10, Wonderful, (10 reviews)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
$245 nightly
The price is $262
Aug 4 - Aug 5
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
TV

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
$261 nightly
The price is $293
Aug 4 - Aug 5
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Interior

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
$519 nightly
The price is $594
Aug 16 - Aug 17
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Coffee/tea maker, fridge, microwave, oven

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
$777 nightly
The price is $906
Jul 23 - Jul 24
Total with taxes and fees
River North Private Deck With In and Out Parking
Property grounds

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, (27 reviews)
"I had a fun stay "
United States
Jusu K.
$194 nightly
The price is $217
Aug 17 - Aug 18
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
1 bedroom

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Chicago
9.6 out of 10, Exceptional, (28 reviews)
"Nice, clean, and a quiet hotel"
United States
Anonymous traveler
$104 nightly
The price is $115
Aug 12 - Aug 13
Total with taxes and fees
Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very Good, (29 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
$282 nightly
The price is $301
Jul 20 - Jul 21
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Interior

Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"My overall experience was great! This 4 bedroom apartment.2 bath with included parking is a great place to stay when you are visiting Chicago and doing activities in the city.The management staff was great to work with. The front desk staff was also great.My family felt safe and we would return.Thigpen Family"
United States
Kimberly T.
$659 nightly
The price is $761
Jul 28 - Jul 29
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 1
Interior

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, (9 reviews)
"Great stay. Nice place. Easy access. Clean. "
United States
Juan S.
$248 nightly
The price is $262
Jul 23 - Jul 24
Total with taxes and fees
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Coffee/tea maker, fridge, microwave, oven

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
$294 nightly
The price is $337
Aug 17 - Aug 18
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
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

River Hotel

River Hotel

10/10 Excellent
"Staff was helpful"
Bilal 2-night trip
Posted 6 hours ago
River Hotel

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 $197 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?

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 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.