42+ Vacation Rentals Near South Shore

NearbyHoliday - Vacation Rentals in South Shore

a bedroom with a large bed and a chandelier at New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking in 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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a living room with a mirror and a couch at BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 in Chicago

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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a living room with a lot of furniture in it at The Brown House - A luxurious UChicago Campus stay in Chicago

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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a living room with a couch and a table at Cozy Woodlawn Retreat 1 in Chicago

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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a living room with a tv and flowers on a table at Cozy & Near Downtown & Hyde Park in Chicago

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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a living room with a red couch and a ceiling fan at Cozy Woodlawn Retreat 2 in Chicago

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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a living room with a couch and a tv and a fireplace at Beautiful Big 3 bedroom Quiet Apt near downtown in Chicago

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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a living room with a couch and a kitchen at Parisian Retreat 6min to Main Quandrangle U of C in Chicago

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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Luxury Places to Stay in South Shore

Over 10+ Luxury Places to Stay in or Near South Shore

a large building with lights in front of it at The Study at the University of Chicago in Chicago

From US $259

The Study at the University of Chicago

9.1 (1047 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Woodlawn • In South Shore · 3.3km to center

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a large building with many windows at night at Sophy Hyde Park in Chicago

From US $258

Sophy Hyde Park

9.0 (202 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Hyde Park • In South Shore · 4.5km to center

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a living room with a couch and a tv and a fireplace at Beautiful Big 3 bedroom Quiet Apt near downtown in Chicago

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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a living room with a mirror and a couch at BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 in Chicago

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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a bedroom with a large bed and a chandelier at New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking in 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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a living room with a green couch and a kitchen at Eco Stay by UChicago, Lakefront & Hyde Park! in Chicago

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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a living room with a lot of furniture in it at The Brown House - A luxurious UChicago Campus stay in Chicago

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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a living room with a blue couch and two chairs at Chateau de Woodlawn - Peaceful 3 bedroom apartment. in Chicago

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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Pet-Friendly Vacation Rentals in South Shore

Over 14+ Pet-Friendly Vacation Rentals in or Near South Shore

a large building with lights in front of it at The Study at the University of Chicago in Chicago

From US $259

The Study at the University of Chicago Pets allowed

9.1 (1047 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Woodlawn • In South Shore · 3.3km to center

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a living room with a couch and a rug with records on it at Greater Grand Crossing/Hyde Park in Chicago

From US $175

Greater Grand Crossing/Hyde Park Pets allowed

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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a bedroom with a bed and a chair and a rug at Luxe Loft vibe with King Suite - 4BR 3Ba in Chicago

From US $405

Luxe Loft vibe with King Suite - 4BR 3Ba Pets allowed

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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a living room with a couch and a table at Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep in Chicago

From US $138

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

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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a living room with a green couch and a kitchen at Eco Stay by UChicago, Lakefront & Hyde Park! in Chicago

From US $270

Eco Stay by UChicago, Lakefront & Hyde Park! Pets allowed

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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a living room with a couch and a tv at Cozy & Radiant 2BR Apartment - BStone 605 in Chicago

From US $159

Cozy & Radiant 2BR Apartment - BStone 605 Pets allowed

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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a brick building with a sign for a motel at Admiral Motel By OYO Chicago I-94 in Chicago

From US $80

Admiral Motel By OYO Chicago I-94 Pets allowed

3.2 (52 Reviews) Hotel

Free on-site parking • Pet friendly • Private bathroom

Chicago Chatham • In South Shore · 4.5km to center

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a living room with a blue couch and a table at Inviting 2-Bedroom Apt in Hyde Park - The Blackwood rep in Chicago

From US $166

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

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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Vacation Rentals in South Shore

Over 33+ Vacation Rentals in or Near South Shore

a bedroom with a large bed and a chandelier at New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking in 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

Best Price Match

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a living room with a mirror and a couch at BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 in Chicago

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

Best Price Match

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a living room with a lot of furniture in it at The Brown House - A luxurious UChicago Campus stay in Chicago

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

Best Price Match

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a living room with a couch and a table at Cozy Woodlawn Retreat 1 in Chicago

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

Best Price Match

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a living room with a tv and flowers on a table at Cozy & Near Downtown & Hyde Park in Chicago

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

Best Price Match

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a living room with a red couch and a ceiling fan at Cozy Woodlawn Retreat 2 in Chicago

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

Best Price Match

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a living room with a couch and a tv and a fireplace at Beautiful Big 3 bedroom Quiet Apt near downtown in Chicago

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

Best Price Match

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a living room with a couch and a kitchen at Parisian Retreat 6min to Main Quandrangle U of C in Chicago

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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Villa Places to Stay in South Shore

Over 2+ Villa Places to Stay in or Near South Shore

a large empty room with a empty keyboard at Lakefront Rooftop Parking in Chicago

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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a living room with a white couch and a tv at A Home Away from Home! in Chicago

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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Hotels in South Shore

Over 9+ Hotels in or Near South Shore

a building on a city street at night at Hyatt Place Chicago-South/University Medical Center in Chicago

From US $169

Hyatt Place Chicago-South/University Medical Center

8.3 (367 Reviews) Hotel

Breakfast • Shuttle service (free) • Pet friendly

Chicago Hyde Park • In South Shore · 4.5km to center

Best Price Match

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a large building with many windows at night at Sophy Hyde Park in Chicago

From US $258

Sophy Hyde Park

9.0 (202 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Hyde Park • In South Shore · 4.5km to center

Best Price Match

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a large building with lights in front of it at The Study at the University of Chicago in Chicago

From US $259

The Study at the University of Chicago

9.1 (1047 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Woodlawn • In South Shore · 3.3km to center

Best Price Match

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a large yellow house with trees in front of it at Pill Hill Mansion in Chicago

From US $35

Pill Hill Mansion

6.7 (402 Reviews) Hostel

Free parking • Free WiFi • Private bathroom

Chicago Calumet Heights • In South Shore · 3.6km to center

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a small bedroom with a bed and a window at Chateau de Woodlawn - Room III - The Dream Catcher in Chicago

From US $76

Chateau de Woodlawn - Room III - The Dream Catcher

7.5 (35 Reviews) Guest_house

Free on-site parking • Free WiFi • Family rooms

Chicago Woodlawn • In South Shore · 3.6km to center

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a bedroom with a large bed with a blue blanket at Chateau de Woodlawn - Room I - La Tour Eiffel in Chicago

From US $81

Chateau de Woodlawn - Room I - La Tour Eiffel

9.5 (13 Reviews) Guest_house

Free on-site parking • Shuttle service (free) • Free WiFi

Chicago Woodlawn • In South Shore · 3.6km to center

Best Price Match

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a living room with a blue couch and chairs at Chateau de Woodlawn - Room II - Le Parisienne in Chicago

From US $76

Chateau de Woodlawn - Room II - Le Parisienne

7.7 (22 Reviews) Guest_house

Free on-site parking • Free WiFi • Non-smoking rooms

Chicago Woodlawn • In South Shore · 3.6km to center

Best Price Match

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a brick building with a sign for a motel at Admiral Motel By OYO Chicago I-94 in Chicago

From US $80

Admiral Motel By OYO Chicago I-94

3.2 (52 Reviews) Hotel

Free on-site parking • Pet friendly • Private bathroom

Chicago Chatham • In South Shore · 4.5km to center

Best Price Match

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Cheap Places to Stay in South Shore

Over 9+ Cheap Places to Stay in or Near South Shore

a large yellow house with trees in front of it at Pill Hill Mansion in Chicago

From US $35

Pill Hill Mansion

6.7 (402 Reviews) Hostel

Free parking • Free WiFi • Private bathroom

Chicago Calumet Heights • In South Shore · 3.6km to center

Best Price Match

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a small bedroom with a bed and a window at Chateau de Woodlawn - Room III - The Dream Catcher in Chicago

From US $76

Chateau de Woodlawn - Room III - The Dream Catcher

7.5 (35 Reviews) Guest_house

Free on-site parking • Free WiFi • Family rooms

Chicago Woodlawn • In South Shore · 3.6km to center

Best Price Match

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a living room with a blue couch and chairs at Chateau de Woodlawn - Room II - Le Parisienne in Chicago

From US $76

Chateau de Woodlawn - Room II - Le Parisienne

7.7 (22 Reviews) Guest_house

Free on-site parking • Free WiFi • Non-smoking rooms

Chicago Woodlawn • In South Shore · 3.6km to center

Best Price Match

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a brick building with a sign for a motel at Admiral Motel By OYO Chicago I-94 in Chicago

From US $80

Admiral Motel By OYO Chicago I-94

3.2 (52 Reviews) Hotel

Free on-site parking • Pet friendly • Private bathroom

Chicago Chatham • In South Shore · 4.5km to center

Best Price Match

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a bedroom with a large bed with a blue blanket at Chateau de Woodlawn - Room I - La Tour Eiffel in Chicago

From US $81

Chateau de Woodlawn - Room I - La Tour Eiffel

9.5 (13 Reviews) Guest_house

Free on-site parking • Shuttle service (free) • Free WiFi

Chicago Woodlawn • In South Shore · 3.6km to center

Best Price Match

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a kitchen with white cabinets and a sink and a microwave at Shared, spacious condo near UChicago and Obama Center in Chicago

From US $126

Shared, spacious condo near UChicago and Obama Center

7.4 (8 Reviews) Guest_house

Free on-site parking • Free WiFi • Private bathroom

Chicago Woodlawn • In South Shore · 4.3km to center

Best Price Match

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a building on a city street at night at Hyatt Place Chicago-South/University Medical Center in Chicago

From US $169

Hyatt Place Chicago-South/University Medical Center

8.3 (367 Reviews) Hotel

Breakfast • Shuttle service (free) • Pet friendly

Chicago Hyde Park • In South Shore · 4.5km to center

Best Price Match

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a large building with many windows at night at Sophy Hyde Park in Chicago

From US $258

Sophy Hyde Park

9.0 (202 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Chicago Hyde Park • In South Shore · 4.5km to center

Best Price Match

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About South Shore Vacation Rentals

Looking for places to stay in South Shore? Compare top options in Chicago.

With more than 42 South Shore vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in South Shore.

Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in South Shore. Prices average US $223 a night.

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

Top Stay Categories in South Shore

Category	Count
Vacation Rentals	33
Pet-Friendly	14
Luxury Rentals	10
Cheap Rentals	9
Hotels	9
Hotels with Suites	2
Villa Rentals	2

Use These Quick Filters to Find a Vacation Rental in South Shore

Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in South Shore.

Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in South Shore. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.

Weather in South Shore

Average temperatures and rainfall by month range to help plan your stay in South Shore.

Mar - May

Avg High17°C / 62°F

Avg Low6°C / 42°F

Rainfall106 mm / 4.2 in

Jun - Aug

Avg High28°C / 83°F

Avg Low18°C / 65°F

Rainfall90 mm / 3.5 in

Sep - Nov

Avg High18°C / 65°F

Avg Low9°C / 48°F

Rainfall70 mm / 2.7 in

Dec - Feb

Avg High3°C / 38°F

Avg Low-5°C / 22°F

Rainfall62 mm / 2.4 in

Other Places to Stay Near South Shore

South Shore Vacation Rental Frequently Asked Questions

There are a lot of options 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: