Greater Grand Crossing Vacation Rentals

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

New 2 Mi to South Shore Beach: Urban Retreat w/Yard
10.0 (1 Review)
3 Bedrooms 6 Guests
10.0 (3 Reviews)
3 Bedrooms 6 Guests
From US $305 per night
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9.6 (986 Reviews)
1 Bedroom 2 Guests
New Superb townhome with Near Lake in vibrant Chicago
10.0 (1 Review)
2 Bedrooms 7 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
10.0 (1 Review)
1 Bedroom 2 Guests
From US $83 per night
4.0 (32 Reviews)
1 Bedroom 2 Guests
10.0 (7 Reviews)
2 Bedrooms 4 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From US $229 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
From US $177 per night
10.0 (6 Reviews)
1 Bedroom 2 Guests
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9.5 (2 Reviews)
7 Bedrooms 20 Guests
10.0 (3 Reviews)
2 Bedrooms 5 Guests
From US $76 per night
9.3 (13 Reviews)
1 Bedroom 2 Guests
From US $187 per night
10.0 (3 Reviews)
1 Bedroom 2 Guests
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9.3 (3 Reviews)
5 Bedrooms 12 Guests
From US $284 per night
10.0 (2 Reviews)
2 Bedrooms 6 Guests
9.3 (3 Reviews)
2 Bedrooms 4 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
9.2 (6 Reviews)
3 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
9.0 (10 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
|
9.0 (4 Reviews)
1 Bedroom 2 Guests
From US $252 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)
1 Bedroom 2 Guests
From US $200 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (2 Reviews)
4 Bedrooms 7 Guests
From US $187 per night
10.0 (1 Review)
1 Bedroom 2 Guests
|
9.0 (1 Review)
3 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
|
9.0 (1 Review)
1 Bedroom 6 Guests
From US $177 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (1 Review)
3 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
9.8 (18 Reviews)
1 Bedroom 2 Guests
From US $215 per night
9.4 (3 Reviews)
2 Bedrooms 4 Guests
9.0 (7 Reviews)
1 Bedroom 2 Guests
9.0 (1 Review)
1 Bedroom 2 Guests
3.8 (18 Reviews)
1 Bedroom 2 Guests
New
2 Bedrooms 3 Guests
9.0 (1 Review)
1 Bedroom 2 Guests
From US $116 per night
3.4 (45 Reviews)
1 Bedroom 2 Guests
From US $204 per night
New
1 Bedroom 2 Guests
8.9 (15 Reviews)
1 Bedroom 2 Guests
From US $450 per night
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New
1 Bedroom 2 Guests
From US $202 per night
New
1 Bedroom 2 Guests
8.8 (4 Reviews)
1 Bedroom 4 Guests
From US $199 per night
New
1 Bedroom 2 Guests
|
8.7 (20 Reviews)
5 Bedrooms 8 Guests
From US $187 per night
New
1 Bedroom 2 Guests
|
8.7 (8 Reviews)
3 Bedrooms 6 Guests
New
1 Bedroom 2 Guests
|
8.7 (3 Reviews)
2 Bedrooms 5 Guests
From US $177 per night
New
1 Bedroom 2 Guests
8.7 (3 Reviews)
5 Bedrooms 10 Guests
8.6 (38 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 2 Guests
|
8.5 (2 Reviews)
1 Bedroom 2 Guests
|
8.5 (2 Reviews)
1 Bedroom 2 Guests
8.4 (16 Reviews)
1 Bedroom 2 Guests

About Greater Grand Crossing Vacation Rentals

With more than 569 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 656.63 ft² on average, with prices averaging US $377 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.

Greater Grand Crossing Vacation Rental Frequently Asked Questions

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 569 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