108+ Rental Villas and Private Getaways in Westchester |
Westchester Villa Rentals
10.0
Exceptional
(21 Reviews)
- Illinois
- Forestview
- 5.82 mi to center
5 Guests
2 Bedrooms
1 Bathroom
House
- Hot Tub
- Parking
- Internet
US $267/Night
For 7 Nights US $1,872
10.0
Exceptional
(2 Reviews)
2002.09 ft²
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Parking
- Internet
US $244/Night
For 7 Nights US $1,708
9.0
Exceptional
(1005 Reviews)
1 Bathroom
Family Friendly
Hotel
- Spa
- Balcony/Terrace
- Breakfast
US $234/Night
For 7 Nights US $1,641
10.0
Exceptional
(5 Reviews)
- Chicago
- La Grange Park
- 0.12 mi to center
7 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $364/Night
For 7 Nights US $2,546
10.0
Exceptional
(1 Review)
- Chicago
- Brookfield
- 0.58 mi to center
1840.63 ft²
13 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $358/Night
For 7 Nights US $2,504
10.0
Exceptional
(3 Reviews)
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $198/Night
For 7 Nights US $1,384
10.0
Exceptional
(1 Review)
750 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- View
US $303/Night
For 7 Nights US $2,122
9.6
Exceptional
(4 Reviews)
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $195/Night
For 7 Nights US $1,366
8.0
Excellent
(6 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $136/Night
For 7 Nights US $949
Luxury Places to Stay in Westchester
Over 99+ Luxury Places to Stay in or Near Westchester
New
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $749/Night
For 7 Nights US $5,242
10.0
Exceptional
(8 Reviews)
- Chicago
- Brookfield
- 0.57 mi to center
2400 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $652/Night
For 7 Nights US $4,567
9.4
Exceptional
(3 Reviews)
- Chicago
- Westchester
- 0.55 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $541/Night
For 7 Nights US $3,787
9.8
Exceptional
(20 Reviews)
- Chicago
- Westchester
- 0.92 mi to center
2000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $535/Night
For 7 Nights US $3,744
New
12 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $525/Night
For 7 Nights US $3,676
New
- Chicago
- Brookfield
- 0.64 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $524/Night
For 7 Nights US $3,671
6.0
Good
(1 Review)
- Chicago
- Brookfield
- 0.02 mi to center
2000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $513/Night
For 7 Nights US $3,594
8.0
Excellent
(3 Reviews)
- Illinois
- Forestview
- 5.87 mi to center
1650 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $511/Night
For 7 Nights US $3,580
10.0
Exceptional
(4 Reviews)
- Chicago
- Brookfield
- 0.40 mi to center
9 Guests
5 Bedrooms
3 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $498/Night
For 7 Nights US $3,487
Top-Rated Villas with a Pool in Westchester
Over 11+ Top-Rated Private Villas with a Pool in or Near Westchester
9.0
Exceptional
(1005 Reviews)
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Spa
- Fireplace/Heating
US $175/Night
For 7 Nights US $1,228
9.0
Exceptional
(1002 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $157/Night
For 7 Nights US $1,099
8.8
Fabulous
(390 Reviews)
400.22 ft²
11 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $164/Night
For 7 Nights US $1,150
8.3
Excellent
(488 Reviews)
418.6 ft²
9 Bathrooms
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $231/Night
For 7 Nights US $1,619
8.2
Excellent
(1004 Reviews)
- Illinois
- Oakbrook Terrace
- 0.98 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $118/Night
For 7 Nights US $829
7.8
Very Good
(1011 Reviews)
- Illinois
- Oakbrook Terrace
- 0.85 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $118/Night
For 7 Nights US $829
7.6
Very Good
(98 Reviews)
- Illinois
- Oakbrook Terrace
- 0.97 mi to center
290.63 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $112/Night
For 7 Nights US $784
7.5
Very Good
(424 Reviews)
322.92 ft²
11 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $130/Night
For 7 Nights US $912
7.4
Very Good
(356 Reviews)
- Illinois
- Oakbrook Terrace
- 0.85 mi to center
503.21 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $166/Night
For 7 Nights US $1,161
Pet-Friendly Villas in Westchester
Over 38+ Pet-Friendly Private Villas in or Near Westchester
8.0
Excellent
(1 Review)
- Illinois
- Forestview
- 5.73 mi to center
8 Guests
2 Bedrooms
1 Bathroom
Pet Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $409/Night
For 7 Nights US $2,862
9.3
Exceptional
(6 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $170/Night
For 7 Nights US $1,191
New
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $209/Night
For 7 Nights US $1,466
New
- Chicago
- Westchester
- 1.54 mi to center
1603.82 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $444/Night
For 7 Nights US $3,108
10.0
Exceptional
(16 Reviews)
14 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $328/Night
For 7 Nights US $2,294
10.0
Exceptional
(1 Review)
- Chicago
- Westchester
- 1.54 mi to center
1600 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $381/Night
For 7 Nights US $2,665
10.0
Exceptional
(1 Review)
- Chicago
- Western Springs
- 0.68 mi to center
3190 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $212/Night
For 7 Nights US $1,485
9.4
Exceptional
(13 Reviews)
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $432/Night
For 7 Nights US $3,027
8.8
Fabulous
(40 Reviews)
- Chicago
- Westchester
- 1.26 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $272/Night
For 7 Nights US $1,902
Large Private Villas in Westchester
Over 9+ Large Villas in or Near Westchester for Groups and Families
8.0
Excellent
(6 Reviews)
- Chicago
- Brookfield
- 0.74 mi to center
2000 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $460/Night
For 7 Nights US $3,218
New
2249.66 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $471/Night
For 7 Nights US $3,295
New
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $548/Night
For 7 Nights US $3,835
9.0
Exceptional
(6 Reviews)
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $378/Night
For 7 Nights US $2,646
New
10 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Pet Friendly
- Parking
- Air Conditioner
US $222/Night
For 7 Nights US $1,554
New
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $801/Night
For 7 Nights US $5,606
New
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $372/Night
For 7 Nights US $2,604
New
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
Unlock the Best Price
New
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Child Friendly
US $216/Night
For 7 Nights US $1,512
Wheelchair Accessible Holiday Homes in Westchester
Over 15+ Wheelchair Accessible Villas and Holiday Homes in or Near Westchester
8.8
Fabulous
(149 Reviews)
353.86 ft²
3 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
US $239/Night
For 7 Nights US $1,673
9.0
Exceptional
(1004 Reviews)
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Breakfast
- Kitchen
US $195/Night
For 7 Nights US $1,365
8.4
Excellent
(101 Reviews)
401.86 ft²
3 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $152/Night
For 7 Nights US $1,066
8.8
Fabulous
(662 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Breakfast
- Kitchen
US $217/Night
For 7 Nights US $1,518
8.0
Excellent
(41 Reviews)
312.15 ft²
6 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $253/Night
For 7 Nights US $1,769
8.6
Fabulous
(1003 Reviews)
- Chicago
- Westchester
- 0.70 mi to center
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Kitchen
- Parking
US $113/Night
For 7 Nights US $793
7.9
Very Good
(138 Reviews)
- Chicago
- Westchester
- 0.71 mi to center
236.81 ft²
5 Bathrooms
Family Friendly
Hotel
- Breakfast
- Parking
- Air Conditioner
US $159/Night
For 7 Nights US $1,115
7.2
Very Good
(317 Reviews)
344.45 ft²
1 Bathroom
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
US $139/Night
For 7 Nights US $974
6.6
Good
(207 Reviews)
239.2 ft²
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Breakfast
- Parking
US $127/Night
For 7 Nights US $889
Westchester Villas, Airbnb and Holiday Homes Under $200
Over 23+ Westchester Private Villas, Airbnb and Holiday Homes Under $200
New
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Kitchen
- Parking
US $106/Night
For 7 Nights US $741
6.2
Good
(319 Reviews)
294.21 ft²
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Breakfast
- Pet Friendly
US $91/Night
For 7 Nights US $634
8.4
Excellent
(1002 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $157/Night
For 7 Nights US $1,096
5.0
Average
(2 Reviews)
- Chicago
- La Grange Park
- 0.69 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $84/Night
For 7 Nights US $588
6.2
Good
(116 Reviews)
236.81 ft²
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
US $96/Night
For 7 Nights US $670
5.0
Average
(1 Review)
- Chicago
- La Grange Park
- 0.33 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $134/Night
For 7 Nights US $938
4.0
Average
(3 Reviews)
- Chicago
- La Grange Park
- 0.82 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $84/Night
For 7 Nights US $588
3.0
Average
(1 Review)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
US $78/Night
For 7 Nights US $546
New
- Chicago
- Fullersburg
- 0.23 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $199/Night
For 7 Nights US $1,390
Instantly Bookable Villa Rentals in Westchester
Over 17+ Instantly Bookable Private Villas in or Near Westchester
8.0
Excellent
(2 Reviews)
- Chicago
- Westchester
- 0.93 mi to center
5 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $284/Night
For 7 Nights US $1,985
New
- Chicago
- Fullersburg
- 0.11 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $329/Night
For 7 Nights US $2,300
New
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $243/Night
For 7 Nights US $1,700
10.0
Exceptional
(2 Reviews)
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $217/Night
For 7 Nights US $1,521
10.0
Exceptional
(2 Reviews)
- Chicago
- Westchester
- 0.73 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $215/Night
For 7 Nights US $1,502
10.0
Exceptional
(1 Review)
1350 ft²
8 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $344/Night
For 7 Nights US $2,405
9.8
Exceptional
(8 Reviews)
2000 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $229/Night
For 7 Nights US $1,606
8.0
Excellent
(2 Reviews)
- Chicago
- Westchester
- 1.22 mi to center
1300 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $454/Night
For 7 Nights US $3,176
10.0
Exceptional
(1 Review)
1227 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $552/Night
For 7 Nights US $3,861
Book a Last Minute Place to Stay in Westchester
About Westchester Vacation Rentals
There are more than 108 incredible getaway rentals that are available in Westchester. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Westchester.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Westchester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Westchester. Places to stay near Westchester are 590.83 ft² on average, with prices averaging US $462 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Westchester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
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Top Private Villas, Resorts, and Rentals in Westchester
| Type | Count |
|---|---|
| Vacation Homes | 62 |
| Holiday Apartments | 11 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Westchester
★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Westchester with BedroomVillas.
Weather in Westchester, IL
View the weather forecast for Westchester before booking your Westchester Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Stay Near Westchester's Top Attractions
A Large Selection of Villas and Vacation Rentals from Around the World Westchester's Research Top Attractions For Your Vacation
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods
Frequently Asked Questions About Westchester?
What are the top hotels or resorts in Westchester?
We provide an array of great vacation destinations in Westchester. If you are looking to stay in or around the Westchester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Westchester:
- Modern 2Bdrm Westchester Home with brand-new out door HOT TUB
- Enamored in Elmhurst
- Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
- Zen in La Grange Park
- Bliss in Brookfield - 5BR, 3BR
- Modern Airport Oasis -Minutes from O'Hare Airport and Downtown Chicago
- 13 Mi to Dtwn Chicago Maywood Home with Fireplace
- Modern 3BR Home w/Huge Backyard | LCP Collection
- Sleeps 10 + Coffee bar + Game Room + Train to CHGO
- Brand new 2BR Apartment in downtown La Grange close to Metra
Which hotel or resort in Westchester is best for families?
Searching for a family-friendly getaway in Westchester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- Brand new 2 BR Apt in downtown La Grange close to Metra!
- Le Méridien Chicago - Oakbrook Center
- Best Western Plus Chicago Hillside
How many hotels, resorts, or rentals are available in Westchester?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 108 in the Westchester area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Westchester.
People Also Ask
Finding the best prices in Westchester
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