Crestwood Vacation Rentals

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Check prices for these dates

Tonight
Jun 20 - Jun 21
Tomorrow
Jun 21 - Jun 22
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Crestwood

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (790)
"Enjoyed this property! Would happily stay here again "
The price is ￥22,136
￥30,254 total
includes taxes & fees
Jun 29 - Jun 30
Sentral Michigan Avenue
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (541)
"Great stay"
The price is ￥22,842
￥26,815 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.6 out of 10, Excellent, (306)
"Super cool spot in a great part of the city."
The price is ￥18,426
￥21,629 total
includes taxes & fees
Jul 6 - Jul 7
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (320)
"Hotel was nice"
The price is ￥50,901
￥62,999 total
includes taxes & fees
Jul 17 - Jul 18
Level Chicago – Old Town
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (424)
"We had an amazing week staying here. Highly recommend!!"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby lounge

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (185)
"Easy and great for extended stay."
The price is ￥29,433
￥34,552 total
includes taxes & fees
Jul 3 - Jul 4
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.4 out of 10, Very Good, (106)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is ￥18,768
￥22,030 total
includes taxes & fees
Jun 30 - Jul 1
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (167)
"Great room, well decorated and appointed. Great location!"
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (163)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is ￥18,426
￥21,629 total
includes taxes & fees
Jul 7 - Jul 8
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (40)
"Our stay was amazing. "
The price is ￥28,953
￥33,988 total
includes taxes & fees
Jun 30 - Jul 1
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (307)
"Nice place to stay"
Kasa South Loop Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | 1 bedroom, desk, laptop workspace, blackout drapes

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.6 out of 10, (36)
"Nice inside room but it’s not safe outside area"
The price is ￥13,676
￥15,452 total
includes taxes & fees
Jun 24 - Jun 25
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (152)
"Great stay, clean room!"
Kasa River North Chicago
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (53)
"Great location, easy stay!"
The price is ￥28,320
￥33,245 total
includes taxes & fees
Jul 3 - Jul 4
Sonder by Marriott Bonvoy Greektown Apartments
LakeHouse
Fridge, microwave, oven, stovetop

LakeHouse

9.6 out of 10, Exceptional, (18)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (121)
"Perfect for what we were looking for!"
Luxury Home Away From Your Home
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Fridge, microwave, oven, stovetop

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.2 out of 10, Wonderful, (5)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym
NEW LUXURY CONDO WITH PATIO DECK
Property grounds

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (165)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK
Beautiful Rustic Cabin for Two!
Exterior

Beautiful Rustic Cabin for Two!

9.8 out of 10, Exceptional, (9)
"This place was very cozy and amazing. Daniel was the greatest host and I would definitely stay here on future trips"
The price is ￥11,348
￥16,784 total
includes taxes & fees
Jun 26 - Jun 27
Beautiful Rustic Cabin for Two!
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
Smart TV

Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

8.4 out of 10, Very Good, (5)
"My stay was very relaxing and amazing I really enjoyed when we arrived everything was clean the block that the property on was very quiet I will definitely stay here again if we needed anything Stephanie was on it I really appreciate your hospitality thank you "
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown 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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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 3-bedroom house with WiFi in peaceful Hazel Crest: You might want to consider this vacation home rental near Crestwood, which offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.