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Westchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Westchester vacation rentals

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

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
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
The price is CA $298
CA $679 total
includes taxes & fees
Oct 25 - Oct 26
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A bedroom with a bed, a bench, a window, and a wall-mounted shelf.

2. Near Brookfield Zoo - King Bed - Sleeps 6

Near Brookfield Zoo - King Bed - Sleeps 6
Westchester
8.0 out of 10, Very good, (2 reviews)
"The apartment was clean and comfortable, and the location was convenient for our stay in Chicago."
United States
Lauren A.
The price is CA $205
CA $402 total
includes taxes & fees
Oct 29 - Oct 30
Near Brookfield Zoo - King Bed - Sleeps 6
A spacious bedroom with a large bed, a desk, and a chair.

3. 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 CA $515
CA $1,173 total
includes taxes & fees
Nov 2 - Nov 3
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
A kitchen with a stainless steel stove, a digital clock, and various utensils.

4. Near Chicago - Sleeps 10 - Westchester

Near Chicago - Sleeps 10 - Westchester
Westchester
The price is CA $205
CA $403 total
includes taxes & fees
Nov 1 - Nov 2
Near Chicago - Sleeps 10 - Westchester
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

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is CA $254
CA $527 total
includes taxes & fees
Oct 29 - Oct 30
LUXE 3 BR, 2 BA + Hot Tub
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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is CA $209
CA $423 total
includes taxes & fees
Oct 21 - Oct 22
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is CA $152
CA $420 total
includes taxes & fees
Nov 2 - Nov 3
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern living room with teal sofas, a coffee table, and a TV.

8. 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 CA $183
CA $226 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A modern building with the name 'SENIORAL' prominently displayed on the facade.

9. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,379 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is CA $202
CA $237 total
includes taxes & fees
Nov 9 - Nov 10
Sentral Michigan Avenue
Lake

10. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (73 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is CA $222
CA $335 total
includes taxes & fees
Nov 2 - Nov 3
Kasa Lake Shore Chicago
Terrace/patio

11. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"The apartment was clean and had everything we needed for a comfortable stay. Highly recommended!"
Italy
Marco
The price is CA $300
CA $501 total
includes taxes & fees
Oct 25 - Oct 26
At Home in Oak Park
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

12. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (289 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
The price is CA $268
CA $307 total
includes taxes & fees
Nov 20 - Nov 21
The Gem Museum Suites
Dining

13. 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, (22 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 CA $95
CA $238 total
includes taxes & fees
Oct 21 - Oct 22
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
A modern kitchen with a large island, bar stools, and a city view.

14. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (543 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is CA $357
CA $453 total
includes taxes & fees
Nov 1 - Nov 2
Level Chicago – Old Town
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

15. 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, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is CA $130
CA $326 total
includes taxes & fees
Nov 2 - Nov 3
Chic Suite/Mins to L Train /Laundry/Free Parking
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

16. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is CA $253
CA $446 total
includes taxes & fees
Oct 27 - Oct 28
Historic Oak Park Home
Private kitchen

17. 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 CA $158
CA $360 total
includes taxes & fees
Oct 27 - Oct 28
1BR Apartment - Walk to Shops - Downtown OAK PARK
A glass elevator with a city view.

18. 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, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is CA $183
CA $405 total
includes taxes & fees
Nov 2 - Nov 3
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A living room with a white sofa, a decorative vase with a plant, a small wooden figurine, and a gold decorative piece on a white coffee table.

19. 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, (6 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 CA $87
CA $610 total
includes taxes & fees
Oct 21 - Oct 22
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
A living room with a grey sofa, a white coffee table, and a grey rug.

20. Small hidden Gem. Location!

Small hidden Gem. Location!
Cicero
9.2 out of 10, Wonderful, (26 reviews)
"Great viby place really enjoyed staying here"
United States
Edward S.
The price is CA $137
CA $314 total
includes taxes & fees
Nov 1 - Nov 2
Small hidden Gem. Location!
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"My stay was very nice here at this hotel. The staff were very helpful and polite. My room was okay with a nice view of the city but it had an unpleasant smell in the room and some of the wall paper was peeling. I still would say I’d stay here again. It was not horrible at all. 4 stars from me."
Tymori 1-night trip
Posted 7 hours ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Westchester

Everything you need to know about Westchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westchester vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Westchester vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westchester vacation rentals we have selected for you start as low as CA $115 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 vacation 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 vacation.

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. 

Explore a world of travel with Expedia

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.