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

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137 Best Vacation Rentals in South Deering (Starting from $110)

2 Mi to Calumet Park and Beach Windy City Escape!
2 Mi to Calumet Park and Beach Windy City Escape!
House
Chicago, IL, USA
2.9k from South Deering center

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

3 Bedrooms8 Guests
New to Booking
$354
Average price / night
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2 Mi to Calumet Park & Beach: Windy City Escape!
2 Mi to Calumet Park & Beach: Windy City Escape!
House
Chicago, IL, 60617, United States
2.9k from South Deering center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$345
Average price / night
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Beautiful 4 bedroom 2 bathroom apartment near everything
Beautiful 4 bedroom 2 bathroom apartment near everything
Apartment
Chicago, IL, USA
4.9k from South Deering center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$250
Average price / night
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Home in the Historic Town of Pullman
Home in the Historic Town of Pullman
House
Chicago, IL, 60628, United States
3.1k from South Deering center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking

4 Bedrooms4 Guests
New to Booking
$170
Average price / night
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Fully Equipped Cozy 4/5 BR
Fully Equipped Cozy 4/5 BR
Apartment
Chicago, IL, USA
5.6k from South Deering center

Apartments, Accommodations, Pools, Lodgings, Hot tubs, Places to stay, Family

4 Bedrooms10 Guests
5.4

Review score

29 reviews

$284
Average price / night
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Quiet 3-bedroom house in amazing Chicago with WiFi & AC. Near Everything!!
Quiet 3-bedroom house in amazing Chicago with WiFi & AC. Near Everything!!
House
Chicago, IL, 60617, United States
4.2k from South Deering center

AC, Internet, No Smoking

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
New Luxurious 5BD-2BA Home-FREE WINE-2CAR Parking
Apartment
Chicago, IL, USA
5.6k from South Deering center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

5 Bedrooms10 Guests
8.7

Fabulous

3 reviews

$464
Average price / night
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Modern \"Blast From The Past\" A Real Retreat 3Bedroom Unit
Modern \"Blast From The Past\" A Real Retreat 3Bedroom Unit
Apartment
Chicago, IL, 60628, United States
4.2k from South Deering center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Toys

4 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$220
Average price / night
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Entire Guest 1bedroom with private entrance
Entire Guest 1bedroom with private entrance
House
Chicago, IL, USA
5.7k from South Deering center

Air Conditioner, Internet, Parking, Child Friendly

1 Bedroom3 Guests
New to Booking
$132
Average price / night
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ConerStone House
ConerStone House
House
Chicago, IL, 60617, United States
4.7k from South Deering center

4 Bedrooms8 Guests
New to Booking
$359
Average price / night
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Beautiful Big 3 bedroom Quiet Apt near downtown
Beautiful Big 3 bedroom Quiet Apt near downtown
Apartment
Chicago, IL, USA
7.0k from South Deering center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

5 Bedrooms8 Guests
8.7

Fabulous

20 reviews

$259
Average price / night
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A Home Away From Home!
A Home Away From Home!
House
Chicago, IL, 60617, United States
4.9k from South Deering center

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

4 Bedrooms8 Guests
9.8

Exceptional

17 reviews

$336
Average price / night
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Gorgeous 4BDR in Chicago,15mins from DWTN
Gorgeous 4BDR in Chicago,15mins from DWTN
Apartment
Chicago, IL, USA
7.1k from South Deering center

Security/Safety, Parking, Air Conditioner, Guest Services, Pet Friendly, Internet, Child Friendly

3 Bedrooms7 Guests
7.4

Good

24 reviews

$222
Average price / night
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Chic Retreat, Chic Retreat \"Your Urban Getaway\"
Chic Retreat, Chic Retreat \"Your Urban Getaway\"
Apartment
Chicago, IL, 60619, United States
4.9k from South Deering center

AC, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

3 Bedrooms9 Guests
6.0

Review score

4 reviews

$419
Average price / night
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Comfortable & Relaxing Charming 3BR unit
Comfortable & Relaxing Charming 3BR unit
Apartment
Chicago, IL, USA
7.1k from South Deering center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms7 Guests
7.7

Good

4 reviews

$213
Average price / night
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Commuter-Friendly Bungalow in Chicago's South Side
Commuter-Friendly Bungalow in Chicago's South Side
House
Chicago, IL, 60617, United States
4.9k from South Deering center

3 Bedrooms5 Guests
New to Booking
$162
Average price / night
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Walk to the Lake! Grill, Fireplace, Sleeps 12
Walk to the Lake! Grill, Fireplace, Sleeps 12
House
Chicago, IL, USA
7.4k from South Deering center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

5 Bedrooms12 Guests
New to Booking
$329
Average price / night
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Spacious 5-bedroom house in charming Chicago on a quiet secluded block.
Spacious 5-bedroom house in charming Chicago on a quiet secluded block.
House
Chicago, IL, 60628, United States
5.1k from South Deering center

5 Bedrooms16 Guests
New to Booking
$609
Average price / night
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The Chic Urban Oasis Near the Lake!
The Chic Urban Oasis Near the Lake!
Apartment
Chicago, IL, USA
8.0k from South Deering center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms8 Guests
7.7

Good

17 reviews

$194
Average price / night
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Beautiful home near WhiteSox Stadium and Downtown Chicago.
Beautiful home near WhiteSox Stadium and Downtown Chicago.
House
Chicago, IL, 60619, United States
5.2k from South Deering center

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

3 Bedrooms10 Guests
New to Booking
$283
Average price / night
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Lakefront Rooftop Parking
Lakefront Rooftop Parking
Villa
IL, USA
8.1k from South Deering center

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

3 Bedrooms16 Guests
8.2

Very Good

6 reviews

$484
Average price / night
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Family-Friendly Home with Style & Space
Family-Friendly Home with Style & Space
House
Chicago, IL, 60619, United States
5.2k from South Deering center

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

4 Bedrooms8 Guests
New to Booking
$394
Average price / night
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Chicago Home Near Navy Pier & Shedd Aquarium!
Chicago Home Near Navy Pier & Shedd Aquarium!
House
Chicago, IL, 60619-7436, United States
5.2k from South Deering center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, TV, Washer

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$236
Average price / night
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Charming 3-bedroom house in brilliant Chicago with WiFi, AC, plenty of sleeping.
Charming 3-bedroom house in brilliant Chicago with WiFi, AC, plenty of sleeping.
House
Chicago, IL, 60619, United States
5.5k from South Deering center

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

3 Bedrooms8 Guests
New to Booking
$364
Average price / night
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Upscale Chatham Home Perfect for Families & Groups
Upscale Chatham Home Perfect for Families & Groups
House
Chicago, IL, 60619, United States
5.6k from South Deering center

AC, Barbecue, Fireplace, Heater, Internet, Microwave, TV

4 Bedrooms10 Guests
New to Booking
$491
Average price / night
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1 Block to Red Line Station: Walkable Chicago Home
1 Block to Red Line Station: Walkable Chicago Home
House
Chicago, IL, 60619, United States
5.6k from South Deering center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Kitchen, Living Area

6 Bedrooms8 Guests
New to Booking
$144
Average price / night
Check Availability
One room and parlor
One room and parlor
Apartment
Chicago, IL, 60628, United States
5.7k from South Deering center

AC, Heater, Internet

1 Bedroom2 Guests
New to Booking
$110
Average price / night
Check Availability

Other accommodation types in South Deering:

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 South Deering.

Stay Near South Deering's Top Attractions

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South Deering Vacation Rentals on the Map

Frequently Asked Questions

You can explore 137 verified vacation rentals in South Deering. 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 South Deering vary depending on the season, property size, and location. Rates typically start from around $110 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 South Deering 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 South Deering welcome pets. Currently, 24 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 South Deering often include amenities such as Fireplace/Heating, Internet, 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.