Hotel In Greenville - Vacation Rentals in Westchester

MainStay Suites Chicago, Hillside From US $138
         

The Drake Oak Brook, Autograph Collection From US $239
         

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8.9 (138 Reviews)
Hotel
  • Air Conditioner
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  • Designated Smoking Area
Hyatt Lodge Oak Brook Chicago From US $175
         

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9.0 (1005 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hyatt House Oak Brook From US $164
         

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8.8 (383 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Le Méridien Chicago - Oakbrook Center From US $225
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Hyatt Lodge Oak Brook Chicago From US $231
         

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8.4 (498 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatt House Chicago Oak Brook From US $197
         

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9.0 (1003 Reviews)
Hotel
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  • Pool
Residence Inn by Marriott Chicago Oak Brook From US $152
         

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8.4 (98 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Westchester

Over 102+ Luxury Places to Stay in or Near Westchester
Bliss in Brookfield - 5BR, 3BR From US $589
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK~ Game Room From US $584
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Buckingham Getaway/Game Room, Fire Pit & Outdoor Lounge From US $509
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Westchester Corporate Stay 5 Beds From US $498
         

New
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Top-Rated Vacation Rentals with a Pool in Westchester

Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Westchester
Hilton Garden Inn Chicago/Oak Brook From US $118
         

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8.2 (1003 Reviews)
Hotel
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  • Pool
Hilton Chicago/Oak Brook Suites From US $118
         

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7.8 (1004 Reviews)
Hotel
  • Air Conditioner
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  • Pool
Hilton Garden Inn Oakbrook Terrace From US $112
         

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7.5 (98 Reviews)
Hotel
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  • Pet Friendly
Hilton Suites Chicago/Oakbrook Terrace From US $166
         

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7.4 (363 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Westchester

Over 42+ Pet-Friendly Vacation Rentals in or Near Westchester
Sleeps 10 + Coffee bar + Game Room + Train to CHGO From US $358
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Duplex Living in Westchester From US $300
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Elmhurst Gem – Ideal Mid-Term Rental, Top Location From US $217
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 3BR Home w/Huge Backyard | LCP Collection From US $400
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • TV
A beautiful home in quiet Westchester From US $432
         

9.4 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
LUXE 3 BR, 2 BA + Hot Tub From US $371
         

8.8 (48 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Large Vacation Homes & Villas in Westchester

Over 7+ Large Vacation Homes & Villas in or Near Westchester
Near O'Hare huge home for all occasions From US $222
         

New
House
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  • Pet Friendly
Enamored in Elmhurst From US $325
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Westchester

Over 11+ Wheelchair Accessible Vacation Homes in or Near Westchester
Chicago Marriott Oak Brook From US $253
         

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8.0 (41 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Residence Inn by Marriott Chicago Oak Brook From US $225
         

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8.8 (665 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Four Points by Sheraton Chicago Westchester/Oak Brook From US $159
         

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7.9 (138 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Four Points by Sheraton Chicago Westchester/Oak Brook From US $118
         

Best Western Plus Chicago Hillside From US $139
         

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7.3 (304 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Chicago Marriott Oak Brook From US $166
         

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8.4 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
DoubleTree by Hilton Chicago - Oak Brook From US $127
         

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6.7 (208 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Best Western Plus Chicago Hillside From US $121
         

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7.6 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Westchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 18+ Westchester Vacation Rentals and Airbnb Places to Stay Under $200
Travel Inn From US $96
         

6.3 (120 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Travel Inn From US $81
         

7.2 (333 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
This 4 bedroom home is Cozy and Family friendly! From US $190
         

New
House
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Updated Apartment ~ 13 Mi to Downtown Chicago From US $171
         

New
Apartment
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  • Bedding/Linens
Welcome to my home! From US $84
         

New
House
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  • Bedding/Linens
  • Wellness Facilities

Instantly Bookable Vacation Homes in Westchester

Over 15+ Instantly Bookable Vacation Homes in or Near Westchester
Modern 2Bdrm Westchester Home with brand-new out door HOT TUB From US $267
         

10.0 (21 Reviews)
House
  • Parking
  • Security/Safety
  • Child Friendly
King Bed, Game Room & Fire Pit | LCP Collection From US $437
         

8.0 (4 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Charming 2-bedroom apartment in fabulous Westchester with AC, WiFi From US $459
         

8.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Spacious Westchester Duplex for Group & Family From US $412
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay From US $266
         

Ultimate Stay w/ Gym & Game Room Broadview From US $552
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Westchester Vacation Rentals

With more than 31 Westchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hotelingreenville and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Westchester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hotelingreenville Westchester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Westchester. Places to stay near Westchester are 160.06 ft² on average, with prices averaging US $157 a night.

Hotelingreenville makes it easy and safe to find and compare vacation rentals in Westchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Westchester

Type Count
Hotels 31

Use these Quick Filters to Find a Vacation Rental in Westchester

Pro Tip: Hotelingreenville makes it easy to compare the best listings on Hotelingreenville homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Hotelingreenville homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Westchester.

Weather in Westchester

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

Other Places to Stay Near Westchester, IL


Westchester Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Westchester?
How many vacation rentals are available in Westchester?

Currently, the total number of properties listed in 2026 is over 31 in the Westchester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Westchester.