Westchester Holiday Rentals from AU$110: Search Short-Term Rentals

Q: 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.

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Our top choices for Westchester holiday rentals

A modern apartment with a living area, a kitchen, and a dining space.

1. Near Chicago - Sleeps 10 - Westchester

Westchester

A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

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

Westchester

"We had a great time at this property while our family explored Chicago. We found everything about the property was awesome for our family. Sitting outside with coffee in the morning was fantastic. Quiet neighborhood and very close to grocery store. We would stay there again. If we had to make any recommendations it would be that the living room could use more seating as we were five adults and had to use kitchen chairs for all to have a seat. I would also consider new sofa downstairs. It sits...

Stephen K.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in microwave, and a central island with bar stools.

3. Near Brookfield Zoo - King Bed - Sleeps 6

Westchester

Lauren A.

A spacious bedroom with a large bed, a desk, and a chair.

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

Westchester

Jenny W.

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

5. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Brenda M

includes taxes & fees

18 Nov - 19 Nov

A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

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

Maywood

Carl T.

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

7. Vibrant House, Walk to Train, Game Room

Brookfield

Chasity D.

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Oak Park

Makenna

includes taxes & fees

17 Nov - 18 Nov

A dining area with a table set for two, a black leather sofa, and a ceiling fan.

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

Berwyn

Cynthia M.

includes taxes & fees

17 Nov - 18 Nov

A modern living room with teal sofas, a coffee table, and a TV.

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

Northlake

Alex H.

includes taxes & fees

17 Nov - 18 Nov

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

11. Wrigleyville Suites

Lakeview

Francisco

includes taxes & fees

16 Nov - 17 Nov

A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

12. King Bed Non-Smoking

Chicago

Anonymous traveller

includes taxes & fees

1 Dec - 2 Dec

A modern kitchen with dark cabinets, stainless steel appliances, and a patterned tile backsplash.

13. 5-minute walk to the largest old school arcade in America! Family friendly.

Brookfield

Ryan S.

includes taxes & fees

16 Nov - 17 Nov

A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

14. Kasa Lake Shore Chicago

Downtown Chicago

Jair

includes taxes & fees

22 Nov - 23 Nov

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

Oak Park

Robin D.

includes taxes & fees

17 Nov - 18 Nov

A hotel room with a bed, desk, chair, and a ceiling fan.

16. Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago

Chicago

Anonymous traveller

includes taxes & fees

14 Dec - 15 Dec

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

17. Chic Urban Retreat Near Wrigley Field w/Parking

Lakeview

Rachael

includes taxes & fees

29 Nov - 30 Nov

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

18. The Gem Museum Suites

Downtown Evanston

Ernest

includes taxes & fees

16 Dec - 17 Dec

A modern kitchen with wooden cabinets, a microwave, and a dartboard on the wall.

19. Logan Square Boho Getaway - Sleeps 6 - Remodeled

Avondale

Telea D.

includes taxes & fees

16 Nov - 17 Nov

A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

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

Belmont Cragin

Jacob

includes taxes & fees

16 Nov - 17 Nov

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Top Westchester Hotel Reviews

Arlo Chicago

10/10 Excellent

"NA"

Freehand Chicago

8/10 Good

"This is a pretty affordable option if you want to be near the heart of downtown, and there are two huge parking garages nearby, so you shouldn’t struggle to find parking if needed (though you should plan on spending about $60-70 a night extra for it). The hotel has a very young, hipster vibe, with a bar and cafe on the first floor that was pretty active when I arrived. The room I got was nice but a bit small; the bed was built into the wall on three sides, so as a tall person I needed to sleep diagonally, meaning two people might not fit. Opt for a king room if this worries you. You could hear quite a bit of traffic noise early in the evening, although this subsided eventually."

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$110 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 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.

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Check prices for these dates

Our top choices for Westchester holiday rentals

1. Near Chicago - Sleeps 10 - Westchester

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

3. 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

5. LUXE 3 BR, 2 BA + Hot Tub

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

7. Vibrant House, Walk to Train, Game Room

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

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

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

11. Wrigleyville Suites

12. King Bed Non-Smoking

13. 5-minute walk to the largest old school arcade in America! Family friendly.

14. Kasa Lake Shore Chicago

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

16. Cozy King bed,Nsmk|Kitchen|Studio 6 Chicago

17. Chic Urban Retreat Near Wrigley Field w/Parking

18. The Gem Museum Suites

19. Logan Square Boho Getaway - Sleeps 6 - Remodeled

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

Find holiday rentals that suit your style

Top Westchester Hotel Reviews

Arlo Chicago

LondonHouse Chicago, Curio Collection by Hilton

Fairmont Chicago at Millennium Park

The Royal Sonesta Chicago Downtown

The Godfrey Hotel Chicago

Congress Plaza Hotel

Freehand Chicago

Hotel Saint Clair- Magnificent Mile

Hilton Chicago O'Hare Airport

Find out more about Westchester

Frequently asked questions

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