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South Shore Vacation Rentals & NearbyHoliday Homes

Find Vacation Rentals in or near South Shore. Find vacation rentals in South Shore, Chicago.

From US $319

New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking

9.1 (18 Reviews) Apartment

The entire place is yours • 158 m² size • Free on-site parking

Chicago Avalon Park • In South Shore · 2.9km to center

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From US $539

BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12

9.7 (6 Reviews) Holiday_home

The entire place is yours • 139 m² size • Free on-site parking

Chicago Greater Grand Crossing • In South Shore · 4.1km to center

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From US $309

The Brown House - A luxurious UChicago Campus stay

10.0 (5 Reviews) Apartment

The entire place is yours • 139 m² size • Free on-site parking

Chicago Woodlawn • In South Shore · 3.5km to center

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From US $434

Cozy Woodlawn Retreat 1

9.8 (4 Reviews) Apartment

The entire place is yours • 111 m² size • Free parking

Chicago Woodlawn • In South Shore · 4.1km to center

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From US $108

Cozy & Near Downtown & Hyde Park

8.8 (31 Reviews) Apartment

The entire place is yours • 120 m² size • Free on-site parking

Chicago South Shore • In South Shore · 1.7km to center

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From US $440

Cozy Woodlawn Retreat 2

9.0 (3 Reviews) Apartment

The entire place is yours • 111 m² size • Free parking

Chicago Woodlawn • In South Shore · 4.1km to center

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From US $172

Beautiful Big 3 bedroom Quiet Apt near downtown

8.5 (23 Reviews) Apartment

The entire place is yours • 149 m² size • Free on-site parking

Chicago South Shore • In South Shore · 1.2km to center

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From US $311

Parisian Retreat 6min to Main Quandrangle U of C

9.7 (3 Reviews) Apartment

The entire place is yours • 139 m² size • Free on-site parking

Chicago Woodlawn • In South Shore · 3.2km to center

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From US $210

Chateau de Woodlawn - Peaceful 3 bedroom apartment.

8.9 (15 Reviews) Apartment

The entire place is yours • 108 m² size • Kitchen

Chicago Woodlawn • In South Shore · 3.6km to center

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From US $175

Greater Grand Crossing/Hyde Park

7.4 (23 Reviews) Apartment

The entire place is yours • 12 m² size • Pet friendly

Chicago Greater Grand Crossing • In South Shore · 4.4km to center

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From US $405

Luxe Loft vibe with King Suite - 4BR 3Ba

9.7 (7 Reviews) Apartment

The entire place is yours • 232 m² size • Free on-site parking

Chicago Woodlawn • In South Shore · 2.0km to center

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From US $311

The Chic Urban Oasis Near the Lake!

7.6 (20 Reviews) Apartment

The entire place is yours • 116 m² size • Free on-site parking

Chicago South Shore • In South Shore · 501m to center

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From US $93

Kenwood Apartments, Downtown Hyde Park

6.8 (65 Reviews) Homestay

Free parking • Balcony • Free WiFi

Chicago Woodlawn • In South Shore · 2.9km to center

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From US $365

Woodlawn Oasis

8.9 (9 Reviews) Holiday_home

The entire place is yours • 20 m² size • Free on-site parking

Chicago Woodlawn • In South Shore · 2.7km to center

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From US $138

Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep

8.8 (6 Reviews) Apartment

The entire place is yours • 58 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.4km to center

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From US $146

Beautiful 4 bedroom 2 bathroom apartment near everything

8.0 (9 Reviews) Apartment

The entire place is yours • 177 m² size • Free on-site parking

Chicago Calumet Heights • In South Shore · 3.5km to center

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From US $150

A secluded bedroom with a private full bathroom

9.1 (20 Reviews) Homestay

Garden • Free WiFi • Free parking

Chicago Hyde Park • In South Shore · 4.1km to center

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From US $159

Cozy & Radiant 2BR Apartment - BStone 605

8.5 (6 Reviews) Apartment

The entire place is yours • 124 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.7km to center

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From US $270

Eco Stay by UChicago, Lakefront & Hyde Park!

9.0 (5 Reviews) Apartment

The entire place is yours • 74 m² size • Free on-site parking

Chicago Woodlawn • In South Shore · 3.8km to center

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From US $754

Lakefront Rooftop Parking

7.6 (10 Reviews) Villa

The entire place is yours • 204 m² size • Free on-site parking

Chicago South Shore • In South Shore · 1.1km to center

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From US $79

Afrique Francaise de Woodlawn 1

9.1 (18 Reviews) Homestay

Free on-site parking • Balcony • Free WiFi

Chicago Woodlawn • In South Shore · 3.6km to center

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From US $166

Inviting 2-Bedroom Apt in Hyde Park - The Blackwood rep

7.5 (7 Reviews) Apartment

The entire place is yours • 67 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.6km to center

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From US $288

A Home Away from Home!

7.4 (7 Reviews) Villa

The entire place is yours • 161 m² size • Free on-site parking

Chicago Calumet Heights • In South Shore · 3.2km to center

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From US $247

Cozy in Hyde Park Greater Grand Crossing

7.1 (7 Reviews) Apartment

The entire place is yours • 12 m² size • Free parking

Chicago Greater Grand Crossing • In South Shore · 4.4km to center

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From US $111

Trendy Studio Apartment in Chicago - Kenwood 103 & 303 rep

8.7 (3 Reviews) Apartment

The entire place is yours • 37 m² size • Pets allowed

Chicago Hyde Park • In South Shore · 4.0km to center

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From US $102

City Charm Studio Apt in Chicago - Kenwood 205

7.6 (5 Reviews) Apartment

The entire place is yours • 37 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.0km to center

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From US $156

Charming 3BD 2BTH Apartment

5.3 (13 Reviews) Apartment

The entire place is yours • 14 m² size • Free on-site parking

Chicago Woodlawn • In South Shore · 3.5km to center

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From US $79

Afrique Francaise de Woodlawn 2

7.5 (16 Reviews) Homestay

Free on-site parking • Balcony • Free WiFi

Chicago Woodlawn • In South Shore · 3.6km to center

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From US $133

1BR Stylish & Modern Chicago Apartment - Kenwood 508 rep

7.7 (3 Reviews) Apartment

The entire place is yours • 65 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.6km to center

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From US $102

Modern and Minimalist Studio Apartment - Bstone 105 and 108 rep

6.5 (4 Reviews) Apartment

The entire place is yours • 39 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.0km to center

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From US $188

Dog-Friendly Apt with Yard 10 Mi to Downtown

7.0 (3 Reviews) Apartment

The entire place is yours • 65 m² size • On-site parking

Chicago Woodlawn • In South Shore · 3.8km to center

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From US $126

Chicago Studio Unit Cozy & Convenient - BStone 226 rep

5.4 (5 Reviews) Apartment

The entire place is yours • 39 m² size • Pet friendly

Chicago Hyde Park • In South Shore · 4.0km to center

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From US $119

Hyde Park Shared Apartments

5.7 (3 Reviews) Apartment

Apartments • Free WiFi • Private bathroom

Chicago Hyde Park • In South Shore · 5.0km to center

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About South Shore Vacation Rentals on NearbyHoliday

Looking for vacation rentals in South Shore? Compare top options in Chicago.

Find a Vacation Rental and Holiday Home in South Shore. Compare 33 family vacation homes, private villas, cottages, cabins, and condos in South Shore.

NearbyHoliday makes it easy to discover vacation rentals in South Shore that work well for families, groups, and longer stays when you want more room than a standard hotel setup.

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Frequently Asked Questions About South Shore Vacation Rentals

There are a lot of vacation rentals in South Shore. If you plan on staying in the South Shore area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in South Shore: