Lodging Image

Westchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Westchester holiday rentals

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is AU$676
includes taxes & fees
30 June - 1 July
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay
Westchester
10.0 out of 10, Exceptional, (1 review)
"Our family had a wonderful time! The apartment was beautiful,clean and cozy.Thank you for accomodating us."
United States
Manuel P.
The price is AU$598
includes taxes & fees
30 June - 1 July
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
Westchester
The price is AU$1,111
includes taxes & fees
30 June - 1 July
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Apartment looked exactly like the photos, very clean, great location, and perfect for our quick stay! The check-in process was very easy and we had no issues. The host is very responsive to any questions or concerns. "
United States
Jessica S.
The price is AU$2,363
includes taxes & fees
30 July - 31 July
ENVITAE Hotel, 4BR Luxury Modern Apartments

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
The price is AU$302
includes taxes & fees
1 July - 2 July
Sentral Michigan Avenue

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$304
includes taxes & fees
30 June - 1 July
LIVN West Loop Chicago Classic Queen Studio

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
"Great place to stay for our girls weekend. Very convenient to everything in the city! We had the second unit and just to know this is a walk up with about 40-45 stairs to get to the unit. "
United States
Dawn P.
Beautiful Unit CHI in Prime River North - 2

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is AU$308
includes taxes & fees
30 June - 1 July
LIVN Millennium Park Downtown Chicago Prem Studio

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is AU$450
includes taxes & fees
1 July - 2 July
Level Chicago – Old Town

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AU$884
includes taxes & fees
6 July - 7 July
River North Rooftop With In and Out Parking 3

2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
10.0 out of 10, Exceptional, (2 reviews)
"Great host very accommodating."
United States
Kali P.
The price is AU$488
includes taxes & fees
3 July - 4 July
2MI to Obama Center - Pet-Friendly near UOC!

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is AU$764
includes taxes & fees
7 July - 8 July
Downtown Chicago Stay with Free In & Out Parking 5

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
The price is AU$1,398
includes taxes & fees
26 July - 27 July
Modern West Loop Gem-City Views & Prime Location 2

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is AU$1,224
includes taxes & fees
9 July - 10 July
Premium Urban 4BR - Perfect Mix of Comfort & Location

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Great place! "
United States
Isabella T.
The price is AU$375
includes taxes & fees
30 June - 1 July
Just remodeled apartment close to airport and mall

2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is AU$183
includes taxes & fees
30 June - 1 July
2 Full Beds | Non-Smoking, Kitchen

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is AU$462
includes taxes & fees
26 July - 27 July
✽ Charming Cottage ✽ close to College/Town/Station

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (101 reviews)
"Everything was good!"
United States
Brio
The price is AU$455
includes taxes & fees
6 July - 7 July
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (50 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is AU$390
includes taxes & fees
6 July - 7 July
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is AU$320
includes taxes & fees
28 July - 29 July
Cozy studio in Andersonville 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.
Save an average of 15% on thousands of hotels when you're signed in

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$237 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Westchester is located in the city centre, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Westchester?

Expedia has 9 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.