Crestwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Vacation Rentals in Crestwood

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (889)
"great food spots all around and beautiful sites to see "
$169 nightly
The price is $198
Sep 2 - Sep 3
Total with taxes and fees
Sentral Michigan Avenue
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, (478)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
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
8.2 out of 10, Very Good, (347)
"Great stay!"
$129 nightly
The price is $151
Aug 25 - Aug 26
Total with taxes and fees
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, (343)
"A lot of good food options walkable distance. "
$197 nightly
The price is $231
Sep 1 - Sep 2
Total with taxes and fees
Level Chicago – Old Town
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (191)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
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, (629)
"Nice view, and walkable area."
$129 nightly
The price is $151
Sep 2 - Sep 3
Total with taxes and fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (207)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
$152 nightly
The price is $179
Sep 14 - Sep 15
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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, (330)
"Great stay"
Kasa South Loop Chicago
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, (176)
"Great location!!!"
$159 nightly
The price is $187
Sep 1 - Sep 2
Total with taxes and fees
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
8.4 out of 10, Very Good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
$149 nightly
The price is $175
Sep 1 - Sep 2
Total with taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (164)
"Great location and very clean! Will definitely be staying again. "
$263 nightly
The price is $309
Sep 2 - Sep 3
Total with taxes and fees
Kasa River North 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
3.8 out of 10, (52)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
$94 nightly
The price is $106
Aug 25 - Aug 26
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
$131 nightly
The price is $154
Sep 22 - Sep 23
Total with taxes and fees
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
$680 nightly
The price is $852
Aug 25 - Aug 26
Total with taxes and fees
Art Villa
Cozy Studio in Hyde Park-Walk to Lake & University
Microwave, oven, stovetop, coffee/tea maker

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
$173 nightly
The price is $194
Sep 2 - Sep 3
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (4)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
$199 nightly
The price is $222
Sep 2 - Sep 3
Total with taxes and fees
Stylish 1BR in West Loop
Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Iron/ironing board, WiFi, bed sheets

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome 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
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
$212 nightly
The price is $248
Sep 7 - Sep 8
Total with taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments
Bright & Roomy 4BR in Pilsen
Interior

Bright & Roomy 4BR in Pilsen

7.8 out of 10, Good, (7)
$268 nightly
The price is $295
Sep 2 - Sep 3
Total with taxes and fees
Bright & Roomy 4BR in Pilsen
Your Perfect 2BR Home w/ Parking
Fridge, microwave, oven, stovetop

Your Perfect 2BR Home w/ Parking

8.0 out of 10, Very Good, (4)
"Great location, close to United Center. Our host was super and was able to help me when I couldn't follow the instructions (lol). Wish I could have had a longer stay."
$228 nightly
The price is $253
Sep 1 - Sep 2
Total with taxes and fees
Your Perfect 2BR Home w/ Parking
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
" Got a very good rate during an event that had filled up many nearby hotels. Lovely sparkling-clean room, rather small, a firm king bed, dresser, & table. It felt cozy, not crowded, enough drawers and closet space, nice-size bathroom with shower-tub. Room has nice ornate details. 10th-floor sunrise view was terrific. Street & park-concert noise was distant. Noisy neighbors in the adjoining room. Staff very friendly, outgoing, helpful. Lovely lobby with high ceilings, ornate decor, lots of seating. Hotel is ornate and lovely, if a little dated. Bar and restaurants in the hotel are fairly expensive. Reasonable breakfast across the side-street, creative bagels two blocks away. Lots more just west in Printers’ Row. Terrific Blues two blocks away. We felt safe walking out after dark. Loved it! We will return!"
Richard 3-night trip
Posted 9 hours ago
Congress Plaza Hotel

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 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: You might want to consider this vacation home rental near Crestwood, which offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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.