Search Vacation Homes in Westchester

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Sep - 21 Sep
In two weeks
26 Sep - 28 Sep
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Vacation Homes in Westchester

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

7.6 out of 10, Good, (9)
"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."
The price is SAR 557
SAR 897 total
includes taxes & fees
22 Sep - 23 Sep
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A Home Away From Home!
Smart TV, fireplace

A Home Away From Home!

9.4 out of 10, Exceptional, (10)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!
Breathtaking home close to Schaumburg, Chicago
Dining

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (70)
"very nice four bedroom home and a great location."
Breathtaking home close to Schaumburg, Chicago
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

5.4 out of 10, (3)
"Great space for large groups. Park across the street is a great "feature"."
The price is SAR 503
SAR 3,314 total
includes taxes & fees
30 Sep - 1 Oct
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Property grounds

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (53)
"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

7.6 out of 10, Good, (10)
"Comfy beds and a great house for kids and adults."
The price is SAR 217
SAR 1,866 total
includes taxes & fees
1 Oct - 2 Oct
4BR Retreat w/ Theater, Game Room & Backyard
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (48)
"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!"
The price is SAR 638
SAR 1,169 total
includes taxes & fees
15 Sep - 16 Sep
✽ Charming Cottage ✽ close to College/Town/Station
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 place to stay. Made our family trip perfect!"
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Fridge, microwave, oven, stovetop

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

2.0 star property
9.6 out of 10, Exceptional, (10)
"Stayed 2 nights nice experience "
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
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
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!
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Terrace/patio

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (9)
"Great"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
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, (56)
"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
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

LUXE 3 BR, 2 BA + Hot Tub

8.8 out of 10, Excellent, (32)
"This property was is in a good neighborhood nice and clean I really enjoy myself Thanks"
The price is SAR 760
SAR 1,483 total
includes taxes & fees
11 Sep - 12 Sep
LUXE 3 BR, 2 BA + Hot Tub
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Fridge, microwave, oven, stovetop

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (10)
"Cosy interior design and very good beds in a quiet neighborhood. We loved it."
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Chicago Buddha's Abode
Fridge, microwave, oven, stovetop

Chicago Buddha's Abode

Chicago Buddha's Abode
Wrigley Field/Lakeview -Entire Home- Large Groups!
Fridge, microwave, oven, stovetop

Wrigley Field/Lakeview -Entire Home- Large Groups!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! We were able to check in earlier than expected, it was very clean and this was in the perfect location for all of our nearby activities! I would recommend to anyone looking for a great place in the Lincoln park/Lakeview area"
Wrigley Field/Lakeview -Entire Home- Large Groups!
2BR Traveler's Favorite, Modern and Clean
Fridge, microwave, oven, stovetop

2BR Traveler's Favorite, Modern and Clean

10.0 out of 10, Exceptional, (1)
"The place was really nice and clean, an excellent stay that ill consider again my next trip to chicago"
The price is SAR 162
SAR 1,261 total
includes taxes & fees
23 Sep - 24 Sep
2BR Traveler's Favorite, Modern and Clean
Cozy 3-bedroom house in family-oriented Melrose Park.
Property grounds

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (21)
"Excellent place to stay and host provided great communication. The house is very nice and we also enjoyed the fire pit and hot tub, too! We highly recommend staying at this house and we will be back soon!"
Cozy 3-bedroom house in family-oriented Melrose Park.
Sleepy Sanctuary
Interior

Sleepy Sanctuary

10.0 out of 10, Exceptional, (12)
"We loved staying here: super easy to check in, well appointed apartment furnished with kids in mind (there was a pack and play, high chair, booster and kid friendly plates/cups). One block from a park, quiet neighborhood. Good host. We’d definitely stay here again!"
Sleepy Sanctuary
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Westchester Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"It was beautiful loved everything. Very aesthetic so cute for pictures."
Cintia 1-night trip
Posted 2 hours ago
citizenM Chicago Downtown

Explore a world of travel with Expedia

Explore a world of travel with Expedia