Westchester Holiday Rentals

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Holiday Rentals in Westchester

Modern 3BR Home w/ Huge Backyard | LCP Collection

Westchester
10.0 out of 10, Exceptional, (1)
"Everything was exactly like we hoped and ghen sum. Great single level floor plan with garage access."
United States
Alva E.
The price is AU$774
includes taxes & fees
7 Jan - 8 Jan 2026
Modern 3BR Home w/ Huge Backyard | LCP Collection

King Bed, Game Room & Fire Pit | LCP Collection

Westchester
6.0 out of 10, (1)
"The house itself was beautiful! The yard was perfect for relaxing, and the home was spacious, comfortable, and very clean.Unfortunately, we did run into a few issues during our stay. The king bed in the master bedroom was broken and could not be used. A maintenance person showed up after hours without any prior notice or communication from the host, which made us uncomfortable letting them in. We decided to forgo use of the main bedroom rather than allow an unannounced visitor. In addition,...
United States
Trey G.
The price is AU$770
includes taxes & fees
7 Jan - 8 Jan 2026
King Bed, Game Room & Fire Pit | LCP Collection

Less is more! Pet friendly Tiny Home near Chicago!

Burr Ridge
9.8 out of 10, Exceptional, (34)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is AU$322
includes taxes & fees
14 Dec - 15 Dec
Less is more! Pet friendly Tiny Home near Chicago!

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (999)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is AU$253
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue

Chicago luxury home suites

2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is AU$233
includes taxes & fees
8 Dec - 9 Dec
Chicago luxury home suites

Modern West Loop Gem-City Views & Prime Location 5

2.0 star property
Downtown Chicago
8.0 out of 10, Very good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is AU$455
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
West Loop Living – Bright 1BR

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"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"
United States
Jacob D.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
Sun-Drenched 1BR Apartment

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$252
includes taxes & fees
1 Jan - 2 Jan 2026
Gold Coast Living: Modern Studio Unit

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is AU$314
includes taxes & fees
11 Dec - 12 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
The One: A 1BR Stay That Feels Like Home

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AU$643
includes taxes & fees
11 Dec - 12 Dec
Your Chicago get Away

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (394)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is AU$630
includes taxes & fees
19 Dec - 20 Dec
South Loop Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is AU$542
includes taxes & fees
14 Dec - 15 Dec
River North Rooftop With In and Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 6

2.0 star property
Downtown Chicago
The price is AU$747
includes taxes & fees
26 Dec - 27 Dec
Downtown Chicago Stay with Free In & Out Parking 6

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Modern West Loop Gem-City Views & Prime Location 4

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
Modern West Loop Gem-City Views & Prime Location 4
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 Westchester Hotel Reviews

Find out more about Westchester

Everything you need to know about Westchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Westchester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westchester holiday rentals we have selected for you start as low as AU$139 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westchester rentals

At Expedia, we put the best Westchester holiday 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 Westchester 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 Westchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westchester. 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 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?

LakeHouse: This holiday home rental outside of Westchester is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Westchester?

Expedia has 6 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.