Westchester Holiday Rentals

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Check prices for these dates

Holiday Rentals in Westchester

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (679)
"I loved this place will be staying again! Love love loved it!"
The price is AU$249
includes taxes & fees
17 Feb - 18 Feb
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (432)
"Very Spacious (Superior two-bedroom apt). Amazing views from the ninth floor. Had everything appliance we needed. Never even need to resupply from the community cabinets. The blinds are not private enough. If you have lights on inside, you can see through easily. The bathroom has a thicker set of blinds but poses the same problem. It's embarrassing to be seen across from other apartment buildings. Also there were some electrical issues in our bedroom/bathroom. The exhaust fan in the bathroom...
The price is AU$164
includes taxes & fees
9 Mar - 10 Mar
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (255)
"wonderful easy accessible ideal for people have stsycation"
The price is AU$209
includes taxes & fees
9 Mar - 10 Mar
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (140)
"My unit was very nice and more than perfect for my needs. It was spacious and quiet. There is little going on in the area in the evenings which I found a bit unnerving as an older adult. You know - there's safety in numbers! "
The price is AU$232
includes taxes & fees
24 Feb - 25 Feb
Sonder The Burnham Apartments

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (288)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AU$353
includes taxes & fees
18 Feb - 19 Feb
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (362)
"Great extended stay with full kitchen and area. "
The price is AU$316
includes taxes & fees
17 Feb - 18 Feb
Kasa Magnificent Mile Chicago

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is AU$223
includes taxes & fees
9 Mar - 10 Mar
Found Chicago powered by Sonder

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (130)
"I love it"
The Neighborhood Hotel-Little Italy

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (256)
"Best place to stay in Chicago. "
Kasa South Loop Chicago

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (124)
"The property is very nice, we will definitely coming back soon "
The price is AU$140
includes taxes & fees
17 Feb - 18 Feb
Kasa River North Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (137)
"Loved it Had to leave early but loved "
The price is AU$210
includes taxes & fees
17 Feb - 18 Feb
Sonder Jewelers Row

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is AU$179
includes taxes & fees
12 Mar - 13 Mar
Sonder The Opal

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (90)
"Great apartment, we were given an extra bedroom which we used as a wardrobe. Well equipped, modern and well decorated. Full cooker, fridge freezer, microwave. We were provided with tablets for laundry and dishwasher. Washing up.liquids, towels and toilet roll. Great shower. Loved the location. We enjoy cities and walking. Trains a very short walks (several L stations). Target was a 15 minute walk, great independent coffee shop 2 mins from entrance. We will use Sonder again. "
The price is AU$212
includes taxes & fees
23 Feb - 24 Feb
Sonder The Plymouth

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (40)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is AU$233
includes taxes & fees
10 Mar - 11 Mar
Sonder Greektown

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is AU$224
includes taxes & fees
17 Feb - 18 Feb
Wrigleyville Suites

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (72)
"Great property, perfect for two people. Easy walk to Wrigley. Stayed there on a couple cold winter days, and being a basement unit, the heater couldn’t keep up very well, so it was a little colder than ideal, but nothing a sweatshirt or extra blanket couldn’t fix. Would definitely go back!"
Wrigley/Southport Corridor Garden Oasis +parking!

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (23)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Bright Garden Studio

8.8 out of 10, Excellent, (17)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is AU$325
includes taxes & fees
17 Feb - 18 Feb
Bright Garden Studio

Chic Chicago Retreat 2 Bedroom Home by RedAwning

3.0 star property
Chic Chicago Retreat 2 Bedroom Home by RedAwning

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (155)
"We love this well stocked condo. The location, off street parking and amenities make it a great home away from home for us. "
NEW LUXURY CONDO WITH PATIO DECK
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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Other types of properties in Westchester you may be interested in

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8499)
"It was lovely "
The price is AU$158
includes taxes & fees
17 Feb - 18 Feb
Congress Plaza Hotel

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1641)
"all good"
The price is AU$222
includes taxes & fees
17 Feb - 18 Feb
L7 Chicago by LOTTE

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (1649)
"I look forward to staying again!"
The price is AU$321
includes taxes & fees
22 Feb - 23 Feb
Hilton 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.

Frequently asked questions

Can I find holiday rentals in Westchester?

Yes, there are holiday rentals close to the most popular sights in Westchester, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Westchester. Make sure you have time to check out the basketball games while you're in the area.

What are some of the best holiday rentals that Westchester has to offer?

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: This holiday home rental outside of Westchester is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals are there in Westchester?

Expedia has 3 holiday rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Galloping Ghost, or get out into nature at a spot like Millennium Park. You’ll find favourite places to visit such as Wrigley Field and Michigan Avenue in the wider area.

What are holiday rentals like in Westchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westchester. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.