Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Crestwood vacation rentals
1. Sentral Michigan Avenue
Sentral Michigan Avenue4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,409 reviews)
9.0/10
Wonderful
(1,409 reviews)
"10/10 2nd time staying here!"
"10/10 2nd time staying here!"
Rosa
$151 nightly
The price is $178
$178 total
Dec 7 - Dec 8
Total with taxes and fees
2. Level Chicago – Old Town
Level Chicago – Old Town4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (559 reviews)
9.2/10
Wonderful
(559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
"Super clean and friendly staff! Would definitely stay here again"Robert Edward
$234 nightly
The price is $274
$274 total
Nov 23 - Nov 24
Total with taxes and fees
3. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (87 reviews)
8.8/10
Excellent
(87 reviews)
"The bathroom was really clean. The beds were really comfortable"
"The bathroom was really clean. The beds were really comfortable"Jair
$202 nightly
The price is $240
$240 total
Nov 22 - Nov 23
Total with taxes and fees
4. At Home in Oak Park
At Home in Oak Park3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
9.6/10
Exceptional
(14 reviews)
"Great location with parking included"
"Great location with parking included"Melissa
$301 nightly
The price is $344
$344 total
Nov 12 - Nov 13
Total with taxes and fees
5. Historic Oak Park Home
Historic Oak Park Home2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
8.8/10
Excellent
(6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."Janette
$311 nightly
The price is $356
$356 total
Nov 16 - Nov 17
Total with taxes and fees
6. Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue Line3.0 star property
Forest Park
$444 nightly
The price is $475
$475 total
Nov 10 - Nov 11
Total with taxes and fees
7. Historic Oak Park Residence
Historic Oak Park Residence2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
9.6/10
Exceptional
(12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"Ann-Marie
$420 nightly
The price is $481
$481 total
Nov 10 - Nov 11
Total with taxes and fees
8. The Oak Park Loft
The Oak Park Loft2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
9.4/10
Exceptional
(8 reviews)
"Good location, nice neighborhood, restaurants close"
"Good location, nice neighborhood, restaurants close"Linda
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.
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Cabins
Condos
Villas
Cottages
Top Crestwood Hotel Reviews
Holiday Inn Express Crestwood by IHG
Holiday Inn Express Crestwood by IHGCrestwood
10/10 Excellent
It was a great trip
It was a great trip
Travis
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago DowntownDowntown Chicago
10/10 Excellent
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
Shatani
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonDowntown Chicago
10/10 Excellent
Beautiful views and great staff to accommodate any needs
Beautiful views and great staff to accommodate any needs
Griffin
ACME Hotel Chicago, Outset Collection by Hilton
ACME Hotel Chicago, Outset Collection by HiltonDowntown Chicago
10/10 Excellent
Three day trip to Chicago. The hotel was a great central location in downtown and a 10 to 15 minute walk to most sites, Navy Pier, River walk, Michigan Avenue, all the great pizza places. The hotel was smaller compared to most which we loved. Room was updated, bathroom very nice and king sized bed very comfortable. We used the blue line to get to and from O’Hare via Clark station (a 12 minute walk from hotel.). We used the red line via Chicago station (10 min walk from hotel) to go see a Cubs...
Three day trip to Chicago. The hotel was a great central location in downtown and a 10 to 15 minute walk to most sites, Navy Pier, River walk, Michigan Avenue, all the great pizza places. The hotel was smaller compared to most which we loved. Room was updated, bathroom very nice and king sized bed very comfortable. We used the blue line to get to and from O’Hare via Clark station (a 12 minute walk from hotel.). We used the red line via Chicago station (10 min walk from hotel) to go see a Cubs...
Claudia
L7 CHICAGO by LOTTE HOTELS
L7 CHICAGO by LOTTE HOTELSDowntown Chicago
10/10 Excellent
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
Erin
citizenM Chicago Downtown
citizenM Chicago DowntownDowntown Chicago
10/10 Excellent
Great location, clean room and friendly staff!
Great location, clean room and friendly staff!
Diani
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoDowntown Chicago
10/10 Excellent
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
Jennifer
Swissotel - Chicago
Swissotel - ChicagoDowntown Chicago
10/10 Excellent
It was okay but, I wish they specified the clearance level for the self parking if we would of have know ahead of time we would of brought our smaller car
It was okay but, I wish they specified the clearance level for the self parking if we would of have know ahead of time we would of brought our smaller car
Brian
Hyatt Regency Chicago
Hyatt Regency ChicagoDowntown Chicago
10/10 Excellent
Wonderful stay in a great location!
Wonderful stay in a great location!
Brooke
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
10/10 Excellent
Great location
Great location
blerina
Le Méridien Essex Chicago
Le Méridien Essex ChicagoDowntown Chicago
10/10 Excellent
Extremely easy check in, attentive and friendly staff, the attached restaurant and staff where great, we where given a credit to use at the restaurant upon check in at the hotel. The rooms are a bit small, but will do if your single or a couple, we feel the like shower design could be better as it causes water to get on the floor, the downside is parking, but it’s the cost of being in a prime location, I would stay again
Extremely easy check in, attentive and friendly staff, the attached restaurant and staff where great, we where given a credit to use at the restaurant upon check in at the hotel. The rooms are a bit small, but will do if your single or a couple, we feel the like shower design could be better as it causes water to get on the floor, the downside is parking, but it’s the cost of being in a prime location, I would stay again
Shamara
Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre DistrictDowntown Chicago
10/10 Excellent
Great location by the Christmas Market in Daily Center. 24 hour coffee and cocoa in lobby was nice.
Great location by the Christmas Market in Daily Center. 24 hour coffee and cocoa in lobby was nice.
Anne
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileDowntown Chicago
10/10 Excellent
The hotel was great. I was placed in a room. Where constructoon was going on outside. I had planned to sleep in, but at 715 the sound of a jack hanmer woke me up.
The hotel was great. I was placed in a room. Where constructoon was going on outside. I had planned to sleep in, but at 715 the sound of a jack hanmer woke me up.
Rudy
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesDowntown Chicago
10/10 Excellent
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two...
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two...
Joanna
Moxy Chicago Downtown
Moxy Chicago DowntownDowntown Chicago
10/10 Excellent
Loved the bar in the lobby with the DJ on the Saturday night. Pretty trendy.
Loved the bar in the lobby with the DJ on the Saturday night. Pretty trendy.
Mik
Fairfield Inn & Suites Chicago Downtown/River North
Fairfield Inn & Suites Chicago Downtown/River NorthDowntown Chicago
10/10 Excellent
This hotel met our expectations. All the city attractions were within a walkable distance. The staff at breakfast was amazing! Shout out to Javier who was so welcoming and friendly :)
This hotel met our expectations. All the city attractions were within a walkable distance. The staff at breakfast was amazing! Shout out to Javier who was so welcoming and friendly :)
Claribeth
Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central LoopDowntown Chicago
10/10 Excellent
Was surprised how nice this hotel was! Great location, nice staff, easy check in. Room was very nice! Only thing that I didn't like was 65$ parking I thought would be included with rate but no validation it was added to rate at check in.
Was surprised how nice this hotel was! Great location, nice staff, easy check in. Room was very nice! Only thing that I didn't like was 65$ parking I thought would be included with rate but no validation it was added to rate at check in.
Laura
Residence Inn Chicago Downtown/Loop
Residence Inn Chicago Downtown/LoopDowntown Chicago
10/10 Excellent
Great location!! Walking distance to museums, Navy Pier, Willis Tower, and everything.
Great location!! Walking distance to museums, Navy Pier, Willis Tower, and everything.
Sergio
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileDowntown Chicago
10/10 Excellent
Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!
Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!
adriana
Residence Inn Chicago Downtown Magnificent Mile
Residence Inn Chicago Downtown Magnificent MileDowntown Chicago
10/10 Excellent
No complaints. We stayed on the 18th floor and never had a long wait for the elevator (like I have experienced in some other places). The kitchenette was well stocked, beds soft and comfortable and bathroom is spacious in which I absolutely love.
No complaints. We stayed on the 18th floor and never had a long wait for the elevator (like I have experienced in some other places). The kitchenette was well stocked, beds soft and comfortable and bathroom is spacious in which I absolutely love.
Vickie
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 $76 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?
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.