Vacation Rentals in Parkside, IL: Compare 10+ Sites & Save

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41 Best Vacation Rentals in Parkside (Starting from $139)

Luxury Retreat Near Local Gems
Luxury Retreat Near Local Gems
House
Tinley Park, IL, USA
0.7k from Parkside center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom7 Guests
New to Booking
$225
Average price / night
Check Availability
Private cozy Apartment 1Bed+1Bath \n“Entire place only for you”\nWiFi-Parking\n\n
Private cozy Apartment 1Bed+1Bath \n“Entire place only for you”\nWiFi-Parking\n\n
Apartment
Tinley Park, IL, 60477, United States
1.1k from Parkside center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking

1 Bedroom3 Guests
New to Booking
$139
Average price / night
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Modern Retreat with Private Pool & Yard, 10 mins to Tinley Ampitheatre home
Modern Retreat with Private Pool & Yard, 10 mins to Tinley Ampitheatre home
House
IL, USA
4.9k from Parkside center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$411
Average price / night
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Ranch Single Level Home near downtown Tinley Park
Ranch Single Level Home near downtown Tinley Park
House
Tinley Park, IL, 60477, United States
2.0k from Parkside center

AC, Heater, Internet, Kitchen, No Smoking, TV, Washer

3 Bedrooms7 Guests
New to Booking
$392
Average price / night
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Executive Family Home in quiet Culdesac
Executive Family Home in quiet Culdesac
Villa
Hazel Crest, IL, USA
6.7k from Parkside center

Pet Friendly, Parking, Air Conditioner, Child Friendly

4 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$232
Average price / night
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Cozy/Private 3 BR nestled on an acre of  Serenity
Cozy/Private 3 BR nestled on an acre of Serenity
House
Tinley Park, IL, 60477, United States
3.3k from Parkside center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$326
Average price / night
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My Prima Karina BEAUTIFUL 4bd 2ba in quiet Chicago Suburb
My Prima Karina BEAUTIFUL 4bd 2ba in quiet Chicago Suburb
House
Oak Forest, IL, 60452, United States
4.4k from Parkside center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.0

Fabulous

17 reviews

$292
Average price / night
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Lovely 2 Bedroom condo located in Matteson
Lovely 2 Bedroom condo located in Matteson
Apartment
Matteson, IL, USA
6.8k from Parkside center

Parking, Air Conditioner, Wheelchair Accessible, Internet, Pet Friendly, Laundry, Child Friendly

9.2

Superb

4 reviews

$150
Average price / night
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NEW! Modern Retreat with Private Pool & Yard
NEW! Modern Retreat with Private Pool & Yard
House
Orland Hills, IL, 60487, United States
4.9k from Parkside center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$408
Average price / night
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Game Room and Deck Family Home in Chicago Area!
Game Room and Deck Family Home in Chicago Area!
House
Matteson, IL, USA
9.3k from Parkside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$593
Average price / night
Check Availability
Extended Stay Country Club Hills  FHS Rental\n
Extended Stay Country Club Hills FHS Rental\n
House
Country Club Hills, IL, 60478, United States
5.3k from Parkside center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
New to Booking
$354
Average price / night
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Country Club Hills FHS Rental\n
Country Club Hills FHS Rental\n
House
Country Club Hills, IL, 60478, United States
5.5k from Parkside center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
New to Booking
$342
Average price / night
Check Availability
Full suburban home 30 mins from downtown Chicago!
Full suburban home 30 mins from downtown Chicago!
House
Country Club Hills, IL, 60478, United States
5.5k from Parkside center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio, TV

4 Bedrooms10 Guests
8.4

Very Good

8 reviews

$291
Average price / night
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Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC
Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC
House
Crestwood, IL, 60445, United States
6.3k from Parkside center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

3 Bedrooms7 Guests
9.8

Exceptional

12 reviews

$261
Average price / night
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Private Home Awaits
Private Home Awaits
House
Homewood, IL, 60430, United States
6.3k from Parkside center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
9.4

Superb

13 reviews

$294
Average price / night
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The Country Life - house
The Country Life - house
House
Markham, IL, 60428, United States
6.9k from Parkside center

AC, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms14 Guests
10.0

Exceptional

3 reviews

$357
Average price / night
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Flossmoor FHS Rental
Flossmoor FHS Rental
House
Flossmoor, IL, 60422, United States
7.1k from Parkside center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
New to Booking
$222
Average price / night
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Cul de sac jacuzzi home
Cul de sac jacuzzi home
House
Country Club Hills, IL, 60478, United States
7.3k from Parkside center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$239
Average price / night
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Extended Stay Flossmoor FHS Rental
Extended Stay Flossmoor FHS Rental
House
Flossmoor, IL, 60422, United States
7.4k from Parkside center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$224
Average price / night
Check Availability
Matteson FHS Rental
Matteson FHS Rental
House
Matteson, IL, 60443, United States
7.7k from Parkside center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
New to Booking
$224
Average price / night
Check Availability
Extended Stay - Crestwood  FHS Rental
Extended Stay - Crestwood FHS Rental
House
Crestwood, IL, 60445, United States
7.8k from Parkside center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
New to Booking
$392
Average price / night
Check Availability
Extended Stay Matteson FHS Rental
Extended Stay Matteson FHS Rental
House
Matteson, IL, 60443, United States
7.9k from Parkside center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
New to Booking
$223
Average price / night
Check Availability
Pool single family house - Spacious 5-bedroom house in peaceful Orland Park
Pool single family house - Spacious 5-bedroom house in peaceful Orland Park
House
Orland Park, IL, 60467, United States
7.9k from Parkside center

AC, Dryer, Heater, Laundry, No Smoking, Washer

5 Bedrooms4 Guests
New to Booking
$381
Average price / night
Check Availability
3-bedroom house in lovely Matteson with cool AC breeze
3-bedroom house in lovely Matteson with cool AC breeze
House
Matteson, IL, 60443, United States
8.0k from Parkside center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$784
Average price / night
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Marvel - 4BR’s, 2 BA & Game Room
Marvel - 4BR’s, 2 BA & Game Room
House
Mokena, IL, 60448, United States
8.2k from Parkside center

AC, Dryer, Internet, Laundry, No Smoking, Washer

4 Bedrooms10 Guests
8.4

Very Good

11 reviews

$423
Average price / night
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Crestwood FHS Rental - #1
Crestwood FHS Rental - #1
House
Crestwood, IL, 60418, United States
8.3k from Parkside center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$392
Average price / night
Check Availability
Pool Single Family Spacious 4-bedroom house in peaceful Orland Park
Pool Single Family Spacious 4-bedroom house in peaceful Orland Park
House
Orland Park, IL, 60467, United States
8.4k from Parkside center

4 Bedrooms6 Guests
New to Booking
$362
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Parkside.

Parkside Vacation Rentals on the Map

Frequently Asked Questions

You can explore 41 verified vacation rentals in Parkside. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Parkside vary depending on the season, property size, and location. Rates typically start from around $139 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Parkside include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Parkside welcome pets. Currently, 27 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Parkside often include amenities such as Fireplace/Heating, Laundry, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.