Best Vacation Homes in Hillside
House
10.0(21 Reviews)
2 Bedrooms
1 Bath
5 Guests
Hot Tub
Parking
Internet
Child Friendly
US $264/Night
7 Nights - US $1,850
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
2002.09 ft²
Fireplace/Heating- Parking
- Internet
- Child Friendly
US $244/Night
7 Nights - US $1,708
Hotel
9.0(1004 Reviews)
1 Bath
Spa
Balcony/Terrace
Breakfast
Kitchen
US $185/Night
7 Nights - US $1,298
Apartment
10.0(13 Reviews)
1 Bedroom
1 Bath
4 Guests
2900 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $156/Night
7 Nights - US $1,093
House
3 Bedrooms
2 Baths
6 Guests
1603.82 ft²
- Fireplace/Heating
View
Pet Friendly- Parking
US $444/Night
7 Nights - US $3,108
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
746 ft²
- Fireplace/Heating
Pool- Pet Friendly
- Kitchen
US $158/Night
7 Nights - US $1,106
Condo
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $223/Night
7 Nights - US $1,558
House
9.4(22 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $332/Night
7 Nights - US $2,321
Hillside Luxury Rentals
House
3 Bedrooms
2 Baths
10 Guests
1851.39 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $591/Night
7 Nights - US $4,140
House
4 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $558/Night
7 Nights - US $3,905
House
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $527/Night
7 Nights - US $3,687
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $525/Night
7 Nights - US $3,676
House
3 Bedrooms
2 Baths
10 Guests
1850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $510/Night
7 Nights - US $3,568
House
9.8(20 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $505/Night
7 Nights - US $3,535
House
4 Bedrooms
2 Baths
10 Guests
2250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $504/Night
7 Nights - US $3,531
House
9.4(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $488/Night
7 Nights - US $3,415
Hillside Pet Friendly Vacation Rentals
Apartment
8.0(6 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $136/Night
7 Nights - US $949
House
4 Bedrooms
2 Baths
10 Guests
2249.66 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $471/Night
7 Nights - US $3,295
Condo
3.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $419/Night
7 Nights - US $2,930
Apartment
8.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $461/Night
7 Nights - US $3,230
House
1 Bedroom
3 Baths
10 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $222/Night
7 Nights - US $1,554
Condo
3.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $423/Night
7 Nights - US $2,960
Condo
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $211/Night
7 Nights - US $1,474
Apartment
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $193/Night
7 Nights - US $1,351
Hillside Large Vacation Homes
House
10.0(9 Reviews)
5 Bedrooms
2 Baths
12 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $348/Night
7 Nights - US $2,434
House
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $548/Night
7 Nights - US $3,835
New
House
1 Bedroom
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $582/Night
7 Nights - US $4,073
House
10.0(16 Reviews)
4 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $325/Night
7 Nights - US $2,278
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1249 ft²
US $485/Night
7 Nights - US $3,393
House
9.2(25 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $344/Night
7 Nights - US $2,411
House
9.0(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $378/Night
7 Nights - US $2,646
House
4 Bedrooms
3 Baths
10 Guests
2347 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $454/Night
7 Nights - US $3,176
Why Choose Rent By Owner for your Hillside Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Hillside
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit can significantly enhance your experience, so consider the climate and local events here in Hillside to ensure your stay in this charming area aligns perfectly with your vacation plans.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for exploring local outdoor activities in the area. This is the peak season when demand for vacation rentals increases, so early booking is recommended.
Average Temperature Daytime: around 80°F - Nighttime: around 65°F
Fall (September to November)
Fall in this destination features pleasant temperatures and beautiful foliage, attracting visitors looking for a scenic escape. Vacation rentals are in high demand, especially during fall festivals and events.
Average Temperature Daytime: around 70°F - Nighttime: around 50°F
Off-Season Highlights
Winter (December to February)
During winter, the area experiences colder temperatures and fewer visitors, offering a quieter stay. It’s an excellent time for budget-friendly bookings with fewer crowds around local attractions.
Average Temperature Daytime: around 40°F - Nighttime: around 25°F
Spring (March to May)
Spring brings milder weather and blooming landscapes, although it’s less busy than summer or fall. This season provides a peaceful setting for those seeking a more relaxed vacation experience.
Average Temperature Daytime: around 60°F - Nighttime: around 40°F
Weekly Weather Forecast for Hillside
How to Book Your Hillside Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Hillside
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck to relax and entertain during your stay.
- Make the most of a spacious backyard perfect for outdoor gatherings or leisure activities.
- Take advantage of on-site parking spaces to conveniently access your vacation rental.
- Benefit from well-maintained gardens that add natural beauty to your outdoor experience.
- Use a barbecue grill setup to savor outdoor meals with family or friends.
- Relish in the availability of outdoor seating areas designed for enjoying the fresh air.
- Explore nearby parks or green spaces that are easily accessible from your accommodation here.
Top Attractions Around Hillside
What attractions are nearby?
Within this inviting destination, you can explore a variety of nearby activities and attractions that showcase the local charm and outdoor beauty of the region, making your stay both enjoyable and memorable.
Family Activities
- Hillside Park: Spend a relaxing day outdoors exploring this local park, perfect for picnics, playgrounds, and family walks in the area.
- The Butterfly Garden: Discover a colorful sanctuary where children can learn about various butterfly species and enjoy interactive displays within the region.
- Hillside Library Family Programs: Participate in engaging storytelling sessions and craft activities designed to entertain and educate children here.
- Local Community Events: Experience the warmth of family-friendly events held throughout the year that showcase the charm and spirit of the area.
Adult Activities
- Exploring local parks and outdoor spaces: You can enjoy peaceful strolls and picnics in the area's scenic parks, offering a relaxing escape within the region.
- Visiting cultural and historical sites: Discover the rich history and local heritage by exploring nearby museums and landmarks that showcase the area's unique past.
- Dining at regional restaurants: Savor delicious cuisine at popular eateries in this destination, where you can experience authentic flavors from the region.
- Shopping at local stores and markets: Browse charming shops and markets nearby to find unique souvenirs and artisanal products during your stay.
Other Places to Stay in Hillside, IL
South shore hospital
Hillside Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining: Sample the region’s authentic flavors by discovering nearby restaurants and cafes that showcase Hillside's culinary scene.
- Plan Your Transportation: Utilize available public transit options or rent a vehicle to easily navigate the area and access popular attractions.
- Respect Neighborhoods: Be mindful of local customs and community guidelines to ensure a respectful and enjoyable stay in this destination.
- Book Smartly: Take advantage of early reservations and season-specific deals to maximize your experience and value during your trip to here.
Transportation Options
- Metra Rail Service: The regional rail network offers convenient transit options for exploring the broader Chicago area from here, making it easy to access major attractions and business hubs.
- Local Bus Services: Public bus routes connect this part of the region with neighboring communities and amenities, providing affordable transportation within the area.
- Taxi and Rideshare Services: Reliable taxi companies and ridesharing apps are readily available, offering flexible transportation choices when visiting local destinations.
- Personal Vehicles and Car Rentals: Driving remains a popular way to get around here, with numerous car rental agencies available for those seeking independence during their stay.
Local Customs Options
- Local Greeting Etiquette: You’ll find that residents here often greet each other with friendly nods or handshakes, reflecting the warm sense of community in this part of Illinois.
- Community Events and Festivals: Participating in neighborhood celebrations, such as local parades and seasonal festivals, offers a glimpse into the region’s vibrant cultural traditions.
- Dining Customs: When dining out, it’s customary to follow American table manners, with an emphasis on casual yet polite interactions typical in Illinois.
- Celebration of American Holidays: Observing national holidays like Independence Day with fireworks and community gatherings is a cherished tradition here, adding to your authentic experience.
Hillside Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Hillside?
There are a lot of options in Hillside. If you plan on staying in the Hillside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillside:
- Modern 2Bdrm Westchester Home with brand-new out door HOT TUB
- Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
- Fully Remodeled Large Home Ready for You & YourFamily to Enjoy
- 13 Mi to Dtwn Chicago Maywood Home with Fireplace
- Modern 3BR Home w/Huge Backyard | LCP Collection
- Ideal Elmhurst 1BR w/Lounge, Pool & Gym nr Metra, by Blueground
- PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
- 2-bedroom haven near Ohare with Wi-Fi, AC in fabulous Bellwood
- King Bed - Entire Home - Private corner lot
- A beautiful home in quiet Westchester
2. How many vacation rentals have private pools in Hillside?
There are 2 vacation rentals with private pools near Hillside. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Hillside are best for families?
If you are looking for a family-friendly vacation home in Hillside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillside:
4. How many Rentbyowner vacation rentals are available in Hillside?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 134 in the Hillside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hillside.
5. What is the cancellation policy for vacation rentals in Hillside, Illinois?
Cancellation policies vary by property. To understand the specific terms and any potential fees, please review the listing details or contact the property owner directly.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing. Confirm these with the owner before completing your reservation to ensure transparency.
7. How do I secure my booking at a vacation rental in this area?
Bookings are secured through the platform's reservation system once you select your dates and complete payment. For any special requests or questions, reaching out to the property owner can help facilitate your reservation.
8. Is it possible to modify or cancel my booking if my plans change?
Modification and cancellation options depend on individual property policies. Please review the specific rental’s cancellation policy and contact the owner for assistance with changes.
9. What amenities are usually included in a Hillside vacation rental?
Most listings highlight amenities such as Wi-Fi, kitchen facilities, and parking. For detailed information about what each property offers, refer to the listing description or contact the owner directly.
Hillside Top Rated Vacation Rentals
Hotel
9.0(1000 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $185/Night
7 Nights - US $1,297
Hotel
8.8(383 Reviews)
11 Baths
400.22 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $164/Night
7 Nights - US $1,150
Hotel
8.2(1374 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $103/Night
7 Nights - US $720
Hotel
8.2(1001 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $118/Night
7 Nights - US $829
Hotel
7.8(1004 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $132/Night
7 Nights - US $926
Hotel
7.7(411 Reviews)
5 Baths
290.63 ft²
- Private Pool
Oceanfront- Pool
Ocean View
US $92/Night
7 Nights - US $647
Hotel
7.5(424 Reviews)
11 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
US $130/Night
7 Nights - US $912
Hotel
7.5(98 Reviews)
1 Bath
290.63 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $112/Night
7 Nights - US $784
