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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Westchester vacation homes

Fridge, microwave, oven, stovetop
Modern 3BR Home w/ Huge Backyard | LCP Collection

Modern 3BR Home w/ Huge Backyard | LCP Collection

Westchester
10.0 out of 10, Exceptional, (1)
"Everything was exactly like we hoped and ghen sum. Great single level floor plan with garage access."
United States
Alva E.
$475 nightly
The price is $508
Jan 8 - Jan 9, 2026
Total with taxes and fees
Modern 3BR Home w/ Huge Backyard | LCP Collection
Fridge, microwave, oven, stovetop
King Bed, Game Room & Fire Pit | LCP Collection

King Bed, Game Room & Fire Pit | LCP Collection

Westchester
6.0 out of 10, (1)
"The house itself was beautiful! The yard was perfect for relaxing, and the home was spacious, comfortable, and very clean.Unfortunately, we did run into a few issues during our stay. The king bed in the master bedroom was broken and could not be used. A maintenance person showed up after hours without any prior notice or communication from the host, which made us uncomfortable letting them in. We decided to forgo use of the main bedroom rather than allow an unannounced visitor. In addition,...
United States
Trey G.
$473 nightly
The price is $506
Jan 8 - Jan 9, 2026
Total with taxes and fees
King Bed, Game Room & Fire Pit | LCP Collection
Fridge, microwave, oven, stovetop
Modern Apt in Trendy Neighborhood w/ Free Parking

Modern Apt in Trendy Neighborhood w/ Free Parking

2.0 star property
Avondale
$159 nightly
The price is $185
Dec 14 - Dec 15
Total with taxes and fees
Modern Apt in Trendy Neighborhood w/ Free Parking
Smart TV
Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities

Des Plaines
9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
$263 nightly
The price is $278
Dec 10 - Dec 11
Total with taxes and fees
Getaway Near ORD With Great Local Amenities
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

La Grange Highlands
10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
$257 nightly
The price is $275
Dec 11 - Dec 12
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Fitness facility
Theater • Game Room • Gym • Firepit • 4BR Home

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

2.0 star property
Belmont Cragin
$449 nightly
The price is $546
Jan 5 - Jan 6, 2026
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
$291 nightly
The price is $308
Dec 10 - Dec 11
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Lisle
9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
$267 nightly
The price is $283
Dec 15 - Dec 16
Total with taxes and fees
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Smart TV
Enamored in Elmhurst

Enamored in Elmhurst

2.0 star property
Elmhurst
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
$465 nightly
The price is $493
Dec 11 - Dec 12
Total with taxes and fees
Enamored in Elmhurst
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Worth
9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
$299 nightly
The price is $319
Dec 10 - Dec 11
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop
Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug

Des Plaines
9.0 out of 10, Wonderful, (4)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
$318 nightly
The price is $340
Dec 10 - Dec 11
Total with taxes and fees
Cozy Home by O'Hare + EV Plug
Paper towels, dining tables
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

streamwood
10.0 out of 10, Exceptional, (2)
"Was nice would recommend staying with you folks"
United States
Richard W.
$393 nightly
The price is $421
Dec 15 - Dec 16
Total with taxes and fees
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Private kitchen
Cozy Home in Suburbs near Chicago - pet friendly

Cozy Home in Suburbs near Chicago - pet friendly

2.0 star property
Bridgeview
$301 nightly
The price is $322
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Home in Suburbs near Chicago - pet friendly
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm

Oak Park
10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
$458 nightly
The price is $524
Dec 11 - Dec 12
Total with taxes and fees
Modern Victorian Vibes ❤️ | Character & Charm
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!

Wood Dale
10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
$371 nightly
The price is $393
Dec 10 - Dec 11
Total with taxes and fees
Wonderful in Wood Dale, right by O’Hare airport!
Private kitchen
Entire home in Lockport, Illinois

Entire home in Lockport, Illinois

2.0 star property
Lockport
$313 nightly
The price is $332
Dec 10 - Dec 11
Total with taxes and fees
Entire home in Lockport, Illinois
Exterior detail
Vintage Urban Retreat

Vintage Urban Retreat

Oak Park
10.0 out of 10, Exceptional, (13)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$446 nightly
The price is $511
Dec 11 - Dec 12
Total with taxes and fees
Vintage Urban Retreat
Interior
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport
10.0 out of 10, Exceptional, (4)
"Amazing property had everything we need! "
United States
Rachel
$367 nightly
The price is $380
Dec 10 - Dec 11
Total with taxes and fees
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Exterior
Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown

Willow Springs
8.8 out of 10, Excellent, (16)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
United States
Gabriela N.
$372 nightly
The price is $398
Dec 10 - Dec 11
Total with taxes and fees
Coziest estate home 20 minutes to downtown
Exterior
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV

PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV

Naperville
9.6 out of 10, Exceptional, (26)
"This property was very clean, spacious and a great place to stay for my family!"
United States
Vanessa P.
$355 nightly
The price is $376
Dec 10 - Dec 11
Total with taxes and fees
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Dpacious,clean,comfortable"
Elizabeth 1-night trip
Posted 7 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Westchester

Westchester Vacation Homes information

Number of reviews
245
Accommodation
728 Vacation Homes
Lowest Price
$275
Highest Price
$546

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