Search Vacation Homes in Westchester

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In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
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Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Homes in Westchester

Our top choices for Westchester vacation homes

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Iron/ironing board, WiFi, bed sheets

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

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

8.0 out of 10, Very Good, (7)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
$226 nightly
The price is $242
Sep 8 - Sep 9
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel crib

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
$750 nightly
The price is $913
Sep 23 - Sep 24
Total with taxes and fees
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Fridge, microwave, oven, stovetop

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very Good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
$431 nightly
The price is $457
Sep 23 - Sep 24
Total with taxes and fees
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

8.0 out of 10, Very Good, (8)
$409 nightly
The price is $497
Sep 23 - Sep 24
Total with taxes and fees
4BR Retreat w/ Theater, Game Room & Backyard
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Fridge, microwave, oven, stovetop

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (53)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square
Chic and Spacious Bi-level 3BD in Bucktown!
Microwave, toaster, cookware/dishes/utensils

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Property was comfortable, clean, and in a great location."
Chic and Spacious Bi-level 3BD in Bucktown!
Breathtaking home close to Schaumburg, Chicago
Dining

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (66)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago
Des Plaines Vacation Rental w/ Spacious Backyard!
Fridge, microwave, stovetop, dishwasher

Des Plaines Vacation Rental w/ Spacious Backyard!

9.0 out of 10, Wonderful, (16)
"Easy access good parking clean well stocked but very small three bedroom house with nice outdoor sitting and eating area near Rosemont"
Des Plaines Vacation Rental w/ Spacious Backyard!
Belmont House, Classy & Chic/walk to Wrigley Field
Interior

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (50)
"Great bang for your buck. Great area and great communication "
Belmont House, Classy & Chic/walk to Wrigley Field
New home w/view & party deck - 2nd Floor
Fridge, microwave, oven, stovetop

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (25)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor
A Home Away From Home!
Smart TV, fireplace

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!
Clarendon Hills Top Floor
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

6.8 out of 10, (10)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (47)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
$295 nightly
The price is $313
Sep 2 - Sep 3
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Furnished Private home in Aurora sleeps 9 guests
Fridge, microwave, oven, stovetop

Furnished Private home in Aurora sleeps 9 guests

9.2 out of 10, Wonderful, (90)
"Great yard to grill in the evening. Front room and family room both have TVs so kids can watch different things than the adults, if that's what you need or want. The couch in the family room is really comfortable to unwind on. Bedrooms all have their own TVs as well. The communication was amazing with the owner. They were incredibly responsive! I would definitely rent from them again if the option arises. "
Furnished Private home in Aurora sleeps 9 guests
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
Fridge, microwave, oven, stovetop

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

10.0 out of 10, Exceptional, (23)
"Great house, great neighborhood, host was amazing!"
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
Feel good, live well in this cozy Wheaton 3 bedroom!
Living area

Feel good, live well in this cozy Wheaton 3 bedroom!

10.0 out of 10, Exceptional, (1)
"Very clean. Spacious, open living area, lots of storage and comfortable beds. "
Feel good, live well in this cozy Wheaton 3 bedroom!
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Fridge, microwave, coffee/tea maker, toaster

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

6.4 out of 10, (5)
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!
Great place to stay in Warrenville
Fridge, microwave, oven, stovetop

Great place to stay in Warrenville

10.0 out of 10, Exceptional, (66)
"We very much enjoyed our stay. We had everything we needed and the house was very clean. "
Great place to stay in Warrenville
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Very nice,everything is around.Highly recommend."
Iuliia 4-night trip
Posted 1 day ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Westchester

Find out more about Westchester

Westchester Vacation Homes information

Number of reviews
173
Accommodation
873 Vacation Homes
Lowest Price
$242
Highest Price
$913

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