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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Crestwood vacation rentals

A dining area with a wooden table and chairs, a ceiling fan, and a couch.

1. Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
6.4 out of 10, (11 reviews)
"Town was quite walkable which was fun. Teddy is very nice. "
United States
India L.
$319 nightly
The price is $341
Oct 28 - Oct 29
Total with taxes and fees
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,390 reviews)
"10/10 2nd time staying here!"
United States
Rosa
$143 nightly
The price is $168
Nov 22 - Nov 23
Total with taxes and fees
Sentral Michigan Avenue
Room

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (76 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
$211 nightly
The price is $251
Nov 4 - Nov 5
Total with taxes and fees
Kasa Lake Shore Chicago
A hotel lobby with a reception desk, a staircase, and a small seating area.

4. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Harvey
10.0 out of 10, Exceptional, (4 reviews)
"Would tell anyone passing through to stop here. Nothing flashy but all essentials met our needs with no fuss. Clean bathroom, working TV, and decent parking spot included."
United States
Anonymous traveler
$68 nightly
The price is $76
Nov 1 - Nov 2
Total with taxes and fees
2 Full Beds | Non-Smoking
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

5. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
$260 nightly
The price is $298
Nov 2 - Nov 3
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern kitchen with a large island, bar stools, and a city view.

6. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (551 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
$208 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

7. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
$428 nightly
The price is $458
Oct 28 - Oct 29
Total with taxes and fees
Romantic Escape - Adult Playhouse with Exotic Dungeon
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

8. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
$157 nightly
The price is $175
Nov 11 - Nov 12
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

9. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
$212 nightly
The price is $238
Oct 28 - Oct 29
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
A living room with a flat-screen TV mounted on a teal-patterned wall, a dark coffee table, a gray sofa, and a dining area in the background.

10. 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
$243 nightly
The price is $273
Nov 10 - Nov 11
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
A corner room with a green upholstered chair, a small round table with a potted plant, and a framed picture on the wall.

11. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
10.0 out of 10, Exceptional, (1 review)
$183 nightly
The price is $205
Nov 3 - Nov 4
Total with taxes and fees
Cozy Urban View Retreat Near Downtown - Sleeps 7
A wooden deck with a railing, a staircase, and a window with a wreath.

12. 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, (36 reviews)
"I had a fun stay "
United States
Jusu K.
$184 nightly
The price is $206
Nov 1 - Nov 2
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A living room with a grey sofa, a white coffee table, and a grey rug.

13. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (26 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
$208 nightly
The price is $223
Nov 3 - Nov 4
Total with taxes and fees
Small hidden Gem. Location!
A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

14. 3BR | Complete & Well-Located Apt in Hyde Park

3BR | Complete & Well-Located Apt in Hyde Park
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Enjoyed our stay. Thank you"
United States
Nicolle C.
$262 nightly
The price is $292
Oct 28 - Oct 29
Total with taxes and fees
3BR | Complete & Well-Located Apt in Hyde Park
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

15. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (16 reviews)
"Perfect spot for our group of 6! More than enough dishes/silverware etc. the house was clean and comfortable. Would definitely stay again if in the area."
United States
Kathy L.
$461 nightly
The price is $475
Oct 28 - Oct 29
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A modern kitchen with dark cabinets, stainless steel appliances, and a patterned tile backsplash.

16. 5-minute walk to the largest old school arcade in America! Family friendly.

5-minute walk to the largest old school arcade in America! Family friendly.
Brookfield
8.6 out of 10, Excellent, (9 reviews)
"A nice house that easily slept 4 kids and 4 adults. There were ants in the house, then than that it was very nice, it was easy to get to the train into Chicago from here."
United States
Ryan S.
$492 nightly
The price is $527
Nov 3 - Nov 4
Total with taxes and fees
5-minute walk to the largest old school arcade in America! Family friendly.
A modern kitchen with stainless steel appliances, white cabinetry, and a black stove.

17. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (2 reviews)
"This made our stay in Chicago very relaxing. Everything was as expected and I do not have any complaints! Would definitely stay here again!"
United States
Matthew H.
$263 nightly
The price is $295
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

18. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
$257 nightly
The price is $286
Oct 28 - Oct 29
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
Private kitchen

19. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (5 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveler
$491 nightly
The price is $606
Oct 29 - Oct 30
Total with taxes and fees
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

20. Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
8.8 out of 10, Excellent, (5 reviews)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
$367 nightly
The price is $388
Oct 28 - Oct 29
Total with taxes and fees
Entire home in Lockport, Illinois
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Fantastic location. On site restaurant served delicious food and friendly service. My room was comfortable, luxurious and clean. Thank you!"
Susan 2-night trip
Posted 1 hour ago
Eurostars Magnificent Mile

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 $89 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 Marquette Park. In the larger area, you’ll find Soldier Field and Gaelic Park.

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.