Greater Grand Crossing Vacation Rentals

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

New Family-Friendly Home with Style & Space
New
4 Bedrooms 8 Guests
10.0 (3 Reviews)
3 Bedrooms 6 Guests
From US $269 per night
|
9.6 (1006 Reviews)
1 Bedroom 2 Guests
New Modern South Shore Retreat Near Lake and Museum
New
6 Bedrooms 12 Guests
|
10.0 (2 Reviews)
4 Bedrooms 12 Guests
|
8.8 (1013 Reviews)
1 Bedroom 2 Guests
New Hyde Park Luxury Stay 5BR Near Lake & UChicago
New
6 Bedrooms 12 Guests
From US $405 per night
10.0 (2 Reviews)
4 Bedrooms 8 Guests
From US $82 per night
4.0 (39 Reviews)
1 Bedroom 2 Guests
|
10.0 (1 Review)
1 Bedroom 2 Guests
New Renovated 1BR in Hyde Park, Near Campus
From US $108 per night
New
1 Bedroom 2 Guests
From US $383 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
10.0 (10 Reviews)
2 Bedrooms 4 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From US $254 per night
10.0 (9 Reviews)
2 Bedrooms 6 Guests
From US $284 per night
10.0 (5 Reviews)
2 Bedrooms 6 Guests
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9.5 (2 Reviews)
1 Bedroom 6 Guests
From US $240 per night
10.0 (4 Reviews)
2 Bedrooms 5 Guests
From US $76 per night
9.3 (13 Reviews)
1 Bedroom 2 Guests
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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9.3 (3 Reviews)
5 Bedrooms 12 Guests
10.0 (3 Reviews)
2 Bedrooms 4 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
From US $159 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
9.0 (10 Reviews)
1 Bedroom 2 Guests
|
9.0 (4 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
|
9.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 7 Guests
9.0 (2 Reviews)
1 Bedroom 2 Guests
From US $197 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (2 Reviews)
3 Bedrooms 6 Guests
From US $182 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.0 (2 Reviews)
4 Bedrooms 7 Guests
From US $180 per night
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
From US $155 per night
10.0 (1 Review)
1 Bedroom 2 Guests
9.8 (18 Reviews)
1 Bedroom 2 Guests
From US $207 per night
9.6 (4 Reviews)
2 Bedrooms 4 Guests
From US $166 per night
New
1 Bedroom 2 Guests
|
9.0 (1 Review)
3 Bedrooms 6 Guests
From US $74 per night
3.4 (48 Reviews)
1 Bedroom 2 Guests
New
2 Bedrooms 4 Guests
|
9.0 (1 Review)
1 Bedroom 2 Guests
3.2 (26 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 2 Guests
|
9.0 (1 Review)
1 Bedroom 2 Guests
From US $450 per night
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New
1 Bedroom 2 Guests
|
9.0 (1 Review)
1 Bedroom 6 Guests
9.0 (1 Review)
3 Bedrooms 6 Guests
From US $131 per night
New
1 Bedroom 4 Guests
8.9 (15 Reviews)
1 Bedroom 2 Guests
From US $125 per night
New
2 Bedrooms 2 Guests
|
8.8 (6 Reviews)
1 Bedroom 4 Guests
From US $114 per night
New
2 Bedrooms 6 Guests
|
8.7 (20 Reviews)
5 Bedrooms 8 Guests
New
2 Bedrooms 6 Guests
From US $485 per night
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8.7 (7 Reviews)
3 Bedrooms 16 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
From US $97 per night
New
2 Bedrooms 4 Guests
8.6 (38 Reviews)
1 Bedroom 2 Guests

About Greater Grand Crossing Vacation Rentals

With more than 574 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 632.35 ft² on average, with prices averaging US $372 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 574 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