Crestwood Vacation Rentals

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Our top choices for Crestwood vacation rentals

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.
$264 nightly
The price is $299
May 4 - May 5
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space

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.
$229 nightly
The price is $258
May 3 - May 4
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry

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.
$537 nightly
The price is $616
May 26 - May 27
Total with taxes and fees
River North Rooftop With In and Out Parking 3

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
$196 nightly
The price is $221
May 10 - May 11
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.8 out of 10, Exceptional, (6 reviews)
$677 nightly
The price is $836
May 1 - May 2
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments

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.
$271 nightly
The price is $308
May 19 - May 20
Total with taxes and fees
West Loop Living – Bright 1BR

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,143 reviews)
"Thank you for the stay"
United States
Marco
$177 nightly
The price is $208
May 25 - May 26
Total with taxes and fees
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (471 reviews)
"Very clean and nice place"
United States
Hector
$272 nightly
The price is $319
May 27 - May 28
Total with taxes and fees
Level Chicago – Old Town

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.
$231 nightly
The price is $260
May 11 - May 12
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
$746 nightly
The price is $850
May 13 - May 14
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6

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.
$172 nightly
The price is $203
May 10 - May 11
Total with taxes and fees
LIVN West Loop Chicago King Studio

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$410 nightly
The price is $506
May 20 - May 21
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views

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
$260 nightly
The price is $295
May 13 - May 14
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
$327 nightly
The price is $384
May 10 - May 11
Total with taxes and fees
Kasa River North Chicago

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.8 out of 10, Excellent, (24 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
$105 nightly
The price is $118
May 5 - May 6
Total with taxes and fees
Beautiful Rustic Cabin for Two!

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Very nice place and reasonable price."
United States
Maya K.
$244 nightly
The price is $288
May 1 - May 2
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 2 BR

Downtown Chicago Stay with Free In & Out Parking 2

Downtown Chicago Stay with Free In & Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location and the in/out parking was very convenient. The apartment was clean and had plenty of room. The Host was very attentive to our needs. "
United States
Patty H.
$591 nightly
The price is $677
May 3 - May 4
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 2

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
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
$179 nightly
The price is $201
May 3 - May 4
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$258 nightly
The price is $296
May 9 - May 10
Total with taxes and fees
The Oak Park Loft

Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Wow, this is a wonderful Place to stay. The host Is very responsive and friendly The apartment is immaculate I recommend this place highly . "
United States
pnina
$183 nightly
The price is $205
May 5 - May 6
Total with taxes and fees
Cozy Well-Equipped Studio Apartment
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 $208 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?

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.