Greater Grand Crossing Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Greater Grand Crossing, Chicago, Illinois, USA

New Stay, Relax & Explore Chicago
8.0 (1 Review)
2 Bedrooms 10 Guests
10.0 (3 Reviews)
3 Bedrooms 6 Guests
From AU $463 per night
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9.6 (986 Reviews)
1 Bedroom 2 Guests
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10.0 (2 Reviews)
4 Bedrooms 12 Guests
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8.8 (1012 Reviews)
1 Bedroom 2 Guests
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10.0 (1 Review)
2 Bedrooms 4 Guests
From AU $125 per night
4.0 (32 Reviews)
1 Bedroom 2 Guests
New 2 Mi to South Shore Beach: Unit w/Balcony & Yard!
New
3 Bedrooms 6 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
New Scott House in Woodlawn - Basement
From AU $71 per night
New
1 Bedroom 2 Guests
10.0 (1 Review)
4 Bedrooms 5 Guests
From AU $376 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (7 Reviews)
2 Bedrooms 4 Guests
From AU $447 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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9.5 (2 Reviews)
7 Bedrooms 20 Guests
10.0 (3 Reviews)
2 Bedrooms 5 Guests
From AU $115 per night
9.3 (13 Reviews)
1 Bedroom 2 Guests
From AU $430 per night
10.0 (2 Reviews)
2 Bedrooms 6 Guests
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9.3 (3 Reviews)
5 Bedrooms 12 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
9.3 (3 Reviews)
2 Bedrooms 4 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
9.2 (6 Reviews)
3 Bedrooms 6 Guests
From AU $387 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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9.2 (5 Reviews)
3 Bedrooms 7 Guests
From AU $381 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (10 Reviews)
1 Bedroom 2 Guests
From AU $366 per night
10.0 (1 Review)
1 Bedroom 4 Guests
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9.0 (4 Reviews)
1 Bedroom 2 Guests
From AU $299 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (2 Reviews)
1 Bedroom 2 Guests
From AU $292 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
9.0 (2 Reviews)
4 Bedrooms 7 Guests
9.8 (17 Reviews)
1 Bedroom 2 Guests
From AU $326 per night
9.4 (3 Reviews)
2 Bedrooms 4 Guests
8.8 (13 Reviews)
2 Bedrooms 5 Guests
8.8 (6 Reviews)
2 Bedrooms 4 Guests
From AU $381 per night
New
1 Bedroom 2 Guests
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9.0 (1 Review)
3 Bedrooms 6 Guests
3.8 (17 Reviews)
1 Bedroom 2 Guests
From AU $369 per night
New
1 Bedroom 2 Guests
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9.0 (1 Review)
1 Bedroom 6 Guests
From AU $129 per night
3.4 (42 Reviews)
1 Bedroom 2 Guests
From AU $367 per night
New
1 Bedroom 2 Guests
9.0 (1 Review)
3 Bedrooms 6 Guests
From AU $682 per night
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New
1 Bedroom 2 Guests
From AU $348 per night
New
1 Bedroom 2 Guests
9.0 (1 Review)
1 Bedroom 2 Guests
From AU $324 per night
New
1 Bedroom 2 Guests
9.0 (1 Review)
1 Bedroom 2 Guests
8.9 (15 Reviews)
1 Bedroom 2 Guests
New
2 Bedrooms 3 Guests
8.8 (4 Reviews)
1 Bedroom 4 Guests
From AU $286 per night
New
1 Bedroom 2 Guests
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8.7 (20 Reviews)
5 Bedrooms 8 Guests
New
2 Bedrooms 4 Guests
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8.7 (8 Reviews)
3 Bedrooms 6 Guests
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8.7 (3 Reviews)
2 Bedrooms 5 Guests
New
1 Bedroom 2 Guests
8.7 (3 Reviews)
5 Bedrooms 10 Guests
8.6 (38 Reviews)
1 Bedroom 2 Guests

About Greater Grand Crossing Vacation Rentals

With more than 571 Greater Grand Crossing vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) 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 an RBO property in Greater Grand Crossing.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Greater Grand Crossing, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO 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 (RBOs), and other popular Airbnb-style properties in Greater Grand Crossing. Places to stay near Greater Grand Crossing are 674.53 ft² on average, with prices averaging AU $577 a night.

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

Frequently Asked Questions About Greater Grand Crossing?

What are the top vacation rentals in Greater Grand Crossing?

How many Rentbyowner vacation rentals are available in Greater Grand Crossing?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 571 in the Greater Grand Crossing 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 Greater Grand Crossing. 

Nearby Neighborhood (3)

Neighborhood Property Count
Washington Park Vacation Rentals in Chicago, Illinois 584
Chatham Vacation Rentals in Chicago, Illinois 192
Englewood Vacation Rentals in Chicago, Illinois 335