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Our top choices for Westchester holiday rentals

1. 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.
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

2. 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
8.0 out of 10, Very good, (30 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is £226
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

3. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is £276
includes taxes & fees
16 Aug - 17 Aug
LUXE 3 BR, 2 BA + Hot Tub

4. 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, (21 reviews)
"Great host and had everything you would need."
United States
Mj2green J.
The price is £139
includes taxes & fees
12 Aug - 13 Aug
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (68 reviews)
"Very nice stay. Close to everything. Host very helpful. "
United States
Tamela S.
The price is £200
includes taxes & fees
17 Aug - 18 Aug
Chic Suite/Mins to L Train /Laundry/Free Parking

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is £248
includes taxes & fees
17 Aug - 18 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!

7. 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, (106 reviews)
"Everything was good!"
United States
Brio
The price is £243
includes taxes & fees
11 Aug - 12 Aug
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

8. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft

9. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (43 reviews)
"Clean and close to all we needed."
United States
Steve O.
The price is £208
includes taxes & fees
1 Sept - 2 Sept
1BR Apartment - Walk to Shops - Downtown OAK PARK

10. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,235 reviews)
"Great property and location."
United States
Michael
The price is £153
includes taxes & fees
31 Aug - 1 Sept
Sentral Michigan Avenue

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.2 out of 10, Wonderful, (5 reviews)
"Excellent place to stay for a family trip. Lovely neighborhood. Check in was a breeze. Very responsive with any questions I had!"
United States
Traci
The price is £325
includes taxes & fees
5 Aug - 6 Aug
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

12. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is £262
includes taxes & fees
18 Aug - 19 Aug
Historic Oak Park Home

13. Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is £442
includes taxes & fees
12 Aug - 13 Aug
Vintage Urban Retreat

14. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is £509
includes taxes & fees
10 Aug - 11 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit

15. Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.4 out of 10, Exceptional, (6 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
Newly Remodeled Gem | Heart of Chicago

16. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (2 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
The price is £361
includes taxes & fees
1 Sept - 2 Sept
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

17. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (9 reviews)
"Great location and super clean!"
United States
Erica
The price is £320
includes taxes & fees
2 Sept - 3 Sept
Kasa Lake Shore Chicago

18. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is £252
includes taxes & fees
23 Aug - 24 Aug
At Home in Oak Park

19. First floor of Historic Oak Park Villa, Grge:2Cars

First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
The price is £319
includes taxes & fees
18 Aug - 19 Aug
First floor of Historic Oak Park Villa, Grge:2Cars
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 £125 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 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 United Center and Wrigley 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.