Women In Travel - Vacation Rentals in Hillside

Modern 2Bdrm Westchester Home with brand-new out door HOT TUB From US $267
         

10.0 (21 Reviews)
House
  • Parking
  • Security/Safety
  • Child Friendly
13 Mi to Dtwn Chicago Maywood Home with Fireplace From US $244
         

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10.0 (2 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
Downtown Elmhurst! Where else would you want to be! From US $419
         

3.6 (4 Reviews)
Condo
  • 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
Ideal Elmhurst 1BR w/Lounge, Pool & Gym nr Metra, by Blueground From US $160
         

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

Luxury Places to Stay in Hillside

Over 125+ Luxury Places to Stay in or Near Hillside
Charming 3BR Ranch in Elmhurst | Mid-Term Ready From US $582
         

Luxury 4BR Home w/Pool Table &Beautiful Kitchen From US $558
         

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
Apartment
  • Air Conditioner
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Hillside

Over 26+ Top-Rated Vacation Rentals with a Pool in or Near Hillside
Hyatt House Chicago Oak Brook From US $197
         

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9.0 (1003 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
Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294 From US $94
         

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8.2 (1296 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Chicago/Oak Brook From US $118
         

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

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7.8 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294 From US $92
         

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7.7 (411 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Hilton Garden Inn Oakbrook Terrace From US $112
         

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7.5 (98 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Hillside

Over 68+ Pet-Friendly Vacation Rentals in or Near Hillside
A beautiful home in quiet Westchester From US $432
         

9.4 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Westchester Retreat King bed From US $444
         

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New
House
  • Air Conditioner
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  • Pet Friendly
LUXE 3 BR, 2 BA + Hot Tub From US $371
         

8.8 (48 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Brand New Studio apart. free parking From US $136
         

8.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet 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
Bright & Cozy Elmhurst Stay 3BR/2BA From US $459
         

8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury 4BR Home w/Pool Table &Beautiful Kitchen From US $454
         

See More Pet-Friendly Vacation Rentals in Hillside on PetFriendly.io

Large Vacation Homes & Villas in Hillside

Over 14+ Large Vacation Homes & Villas in or Near Hillside
Enamored in Elmhurst From US $325
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Near O'Hare huge home for all occasions From US $222
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming ModernRetro Home! From US $344
         

9.2 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
national historic home near downtown airports no parties no events From US $300
         

9.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Wheelchair Accessible Vacation Homes in Hillside

Over 30+ Wheelchair Accessible Vacation Homes in or Near Hillside
Blueground | Elmhurst, pool, nr Elmhurst Art Museum From US $193
         

The Drake Oak Brook, Autograph Collection From US $239
         

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8.9 (138 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Le Méridien Chicago - Oakbrook Center From US $225
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Blueground | Elmhurst, pool, nr Elmhurst Art Museum From US $178
         

Blueground | Elmhurst, pool, nr Elmhurst Art Museum From US $172
         

Hillside Vacation Rentals and Airbnb Places to Stay Under $200

Over 41+ Hillside Vacation Rentals and Airbnb Places to Stay Under $200
Whole house near city with private parking From US $138
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Blueground | Elmhurst, pool, nr Elmhurst Art Museum From US $167
         

Four Points by Sheraton Chicago Westchester/Oak Brook From US $118
         

Blueground | Elmhurst, pool & gym, nr parks From US $164
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
MainStay Suites Chicago, Hillside From US $138
         

Instantly Bookable Vacation Homes in Hillside

Over 36+ Instantly Bookable Vacation Homes in or Near Hillside
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay From US $266
         

NEW - 5 mins from Elmhurst Uni - Elmhurst Hospital - Pet Friendly From US $399
         

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

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Game Room + Outdoor BBQ Grill | LCP Collection From US $344
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • TV
13 Mi to Dtwn Chicago: Maywood Home w/Fireplace From US $229
         

9.8 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bright Westchester Escape ~ 13 Mi to Downtown From US $217
         

About Hillside Vacation Rentals

With more than 134 Hillside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Womenintravel 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 Hillside.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Womenintravel Hillside, 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 Hillside. Places to stay near Hillside are 585.58 ft² on average, with prices averaging US $415 a night.

Womenintravel makes it easy and safe to find and compare vacation rentals in Hillside 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 Hillside

Type Count
Vacation Homes 69
Hotels 32
Holiday Apartments 27
Villas 1

Use these Quick Filters to Find a Vacation Rental in Hillside

Pro Tip: Womenintravel makes it easy to compare the best listings on Womenintravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Womenintravel 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 Hillside.

Weather in Hillside

View the weather forecast for Hillside before booking your Hillside 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 Hillside, IL


Hillside Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 134 in the Hillside area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Hillside.