Westchester Vacation Rentals from ￥11,950: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Westchester has to offer?

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

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Our top choices for Westchester vacation rentals

Coffee/tea maker, fridge, microwave, oven

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

Westchester

Carl M.

￥69,498 total

includes taxes & fees

Sep 22 - Sep 23

2 bedrooms, iron/ironing board, travel crib, WiFi

2. Near Chicago - Sleeps 10 - Westchester

Westchester

￥40,787 total

includes taxes & fees

Sep 29 - Sep 30

3. Near Brookfield Zoo - King Bed - Sleeps 6

Westchester

4 bedrooms, desk, iron/ironing board, travel crib

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

Westchester

Jenny W.

￥129,556 total

includes taxes & fees

Sep 22 - Sep 23

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

Maywood

Eduardo

￥47,077 total

includes taxes & fees

Sep 21 - Sep 22

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

Berwyn

Garrett C.

￥26,309 total

includes taxes & fees

Sep 21 - Sep 22

7. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Jeff

￥58,237 total

includes taxes & fees

Sep 21 - Sep 22

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

Forest Park

Josh H.

￥53,720 total

includes taxes & fees

Sep 27 - Sep 28

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Top Westchester Hotel Reviews

Travelodge by Wyndham Downtown Chicago

8/10 Good

"We got a suite but it had a strange layout with what looked like a shower area that was just unfinished. Other than that, the room was spacious."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"liked the location of the hotel, room was nice, the restaurant in the hotel adds to the convenience of the property. I did not like EXPEDIA adding extra charges to my bill tried to get them removed but I couldn't get on web site in order to do it. I did not order the insurance and was charged, next trip I will make sure I don't use Expedias web site."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good

"There were a couple of things about this hotel that threw me for a loop (no in room coffee machine -- but plenty of coffee at the bar with choice of skim, half and half and cream; you first encounter the bar versus the registration area), but I would definitely stay here again, and for that I compliment the staff. Fatima greeted us at check in and immediately noticed my daughter had mobility issues and offered to change our room for an accessible one. Since this was my first overnight trip with my daughter I hadn't even thought of that! I appreciated that she saw a way to make our stay better and made it happen. Fatima also always had a smile on her face when we saw her and was always ready to answer any question. I didn't get the name of the doorman we interacted with the most (but I did get a photo with him!), which I regret. He was an older many who worked day shift and he touched my heart when he stayed by my daughter while I went to get our car from the parking garage. He didn't have to do that. The people definitely made this staff wonderful!"

Find out more about Westchester

Search for holiday rentals in Westchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Westchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Westchester!

Frequently asked questions

Can I find vacation rentals in Westchester?

Yes, you can find vacation rentals close to popular points of interest in Westchester, or you can select a secluded option if you want a relaxing place to 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 vacation rentals that Westchester has to offer?

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

How many vacation rentals are there in Westchester?

Expedia has 5 vacation 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 favorite places to visit like Wrigley Field and Soldier Field in the larger area.

What are vacation rentals like in Westchester?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Westchester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

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Check prices for these dates

Our top choices for Westchester vacation rentals

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

2. Near Chicago - Sleeps 10 - Westchester

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. 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

7. LUXE 3 BR, 2 BA + Hot Tub

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

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

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

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

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

13. A quiet stay while you are away

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

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

16. At Home in Oak Park

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

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

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

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

Find vacation rentals that suit your style

Top Westchester Hotel Reviews

Travelodge by Wyndham Downtown Chicago

L7 Chicago by LOTTE

The Wade

Hilton Chicago

Eurostars Magnificent Mile

Hotel Saint Clair- Magnificent Mile

InterContinental Chicago Magnificent Mile by IHG

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Hampton Inn Chicago Downtown/Magnificent Mile

Find out more about Westchester

Frequently asked questions

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