A calm lake with ducks, autumn trees, and a grassy park area.

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Our top choices for Westchester holiday rentals

1. 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
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is £330
includes taxes & fees
22 Sept - 23 Sept
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

2. Near Chicago - Sleeps 10 - Westchester

Near Chicago - Sleeps 10 - Westchester
Westchester
The price is £197
includes taxes & fees
21 Sept - 22 Sept
Near Chicago - Sleeps 10 - Westchester

3. Near Brookfield Zoo - King Bed - Sleeps 6

Near Brookfield Zoo - King Bed - Sleeps 6
Westchester
The price is £194
includes taxes & fees
29 Sept - 30 Sept
Near Brookfield Zoo - King Bed - Sleeps 6

4. 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
10.0 out of 10, Exceptional, (1 review)
"Cute house with easy access to shopping and interstate"
United States
Jenny W.
The price is £619
includes taxes & fees
21 Sept - 22 Sept
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

5. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is £232
includes taxes & fees
23 Sept - 24 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

6. Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Berwyn
9.2 out of 10, Wonderful, (21 reviews)
"Great little place not far from downtown. Clean apartment and a comfortable bed. Daughter slept on the couch and said it wasn't too bad. Everything worked as expected with no issues. Can hear people walking up the steps from time to time but overall pretty quiet. Took some time to find a parking spot but not the host's fault. Overall a great experience and would stay again."
United States
Garrett C.
The price is £129
includes taxes & fees
23 Sept - 24 Sept
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

7. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (60 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is £278
includes taxes & fees
21 Sept - 22 Sept
LUXE 3 BR, 2 BA + Hot Tub

8. Experience Forest Park living near Top Places like downtown Chicago

Experience Forest Park living near Top Places like downtown Chicago
Forest Park
9.4 out of 10, Exceptional, (18 reviews)
"Good location for visiting family just outside Chicago."
United States
Josh H.
The price is £265
includes taxes & fees
27 Sept - 28 Sept
Experience Forest Park living near Top Places like downtown Chicago

9. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
10.0 out of 10, Exceptional, (32 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is £147
includes taxes & fees
13 Oct - 14 Oct
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

10. Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
9.4 out of 10, Exceptional, (40 reviews)
"Beautiful clean and comfy loved my stay"
United States
Tania W.
The price is £151
includes taxes & fees
21 Sept - 22 Sept
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

11. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (71 reviews)
"Easy access to the Green Line."
United States
Michael
The price is £176
includes taxes & fees
29 Sept - 30 Sept
Chic Suite/Mins to L Train /Laundry/Free Parking

12. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is £123
includes taxes & fees
21 Sept - 22 Sept
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

13. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
The price is £227
includes taxes & fees
12 Oct - 13 Oct
A quiet stay while you are away

14. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is £411
includes taxes & fees
21 Sept - 22 Sept
Theater • Game Room • Gym • Firepit • 4BR Home

15. 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, (113 reviews)
"Very clean, spacious living area, and convenient location"
United States
Clara B.
The price is £210
includes taxes & fees
29 Sept - 30 Sept
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

16. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is £255
includes taxes & fees
13 Oct - 14 Oct
At Home in Oak Park

17. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (80 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is £230
includes taxes & fees
22 Sept - 23 Sept
Cozy, Comfortable and Convenient apartment. Close to everything!

18. Accessible 1BR Suite w/ Tub | Free Daily Breakfast

Accessible 1BR Suite w/ Tub | Free Daily Breakfast
York Center
The price is £144
includes taxes & fees
27 Sept - 28 Sept
Accessible 1BR Suite w/ Tub | Free Daily Breakfast

19. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is £315
includes taxes & fees
22 Sept - 23 Sept
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

20. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
The price is £203
includes taxes & fees
29 Sept - 30 Sept
1BR Apartment - Walk to Shops - Downtown OAK PARK
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, apart-hotels, 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 favorite 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 depends 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 £57 per night. Entering your travel dates in the search wizard you might find 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 5 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 Soldier Field 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.