Bespoke Usa Travel - Vacation Rentals in South Shore

Lit & Trendy 1-Bedroom Apt in the Iconic Hyde Park From US $83
         

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5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Child Friendly
  • Internet
Sophy Hyde Park From US $251
         

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9.6 (1000 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Luxury Stay on UChicago Campus 11 min walk to hospitals From US $432
         

High-end 2Bdrm Garden Apt. Where Comfort Meets Style From US $262
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Gorgeous 4BDR in Chicago/15mins from DWTN Brand New! From US $242
         

Luxury Places to Stay in South Shore

Over 450+ Luxury Places to Stay in or Near South Shore
Sophy Hyde Park From US $2,333
         

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9.1 (220 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
1BR Tranquil Hyde Park Apartment - Harper 202 & 402 rep From US $1,600
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Luxury off the Lake From US $828
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
3BR Vibrant Apartment in Hyde Park - Bstone 5310-1 From US $810
         

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6.5 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Modern & Spacious 3BR Apt with In-Unit Laundry - Bstone 2 From US $659
         

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9.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Condo in Hyde park 2 min UofC 6mi downtown From US $558
         

New
Condo
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in South Shore

Over 3+ Top-Rated Vacation Rentals with a Pool in or Near South Shore
UChicago, Shops + Eats, Lake | Gym + W&D | Zencity From US $152
         

2.5 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in South Shore

Over 175+ Pet-Friendly Vacation Rentals in or Near South Shore
Studio Apt Comfy & Sunlit From US $178
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Luxe Loft vibe with King Suite - 4BR 3Ba From US $405
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Studio Unit | Chic + Prime Location From US $155
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Contemporary 2BR Apartment in Vibrant Hyde Park From US $253
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
< 2 Mi to UChicago: Pet-Friendly Getaway w/Yard From US $174
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Charm Studio Apt in Chicago From US $155
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Modern Studio Near UChicago From US $155
         

9.6 (11 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Furnished 3BR Apt w/Laundry From US $194
         

9.6 (4 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Large Vacation Homes & Villas in South Shore

Over 36+ Large Vacation Homes & Villas in or Near South Shore
Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen From US $377
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Remodeled Chicago Apartment < 9 Mi to Downtown From US $489
         

9.6 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
LakeHouse with rooftop and views of lake. From US $362
         

9.4 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Woodlawn Oasis.10 Minutes to Dining & Downtown From US $467
         

9.2 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Delightful 5-bedroom house with AC in vibrant Chicago From US $312
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety

Wheelchair Accessible Vacation Homes in South Shore

Over 129+ Wheelchair Accessible Vacation Homes in or Near South Shore
FRONTDESK Refreshed 1BR Apt in Hyde Park From US $54
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • View
  • Wheelchair Accessible
Hyatt Place Chicago-South/University Medical Center From US $158
         

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8.8 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Stylish 4BR South Loop Home From US $357
         

10.0 (2 Reviews)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Bright South Hyde Park Studio From US $155
         

10.0 (1 Review)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Perfect 1BR Spot near Attractions From US $165
         

7.8 (6 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Wheelchair Accessible
Smart Stay in Hyde Park 1BR From US $247
         

New
Apartment
  • Pet Friendly
  • TV
  • Wheelchair Accessible
Blueground | Hyde Park, AC, w/d, nr museum From US $166
         

South Shore Varoom and Airbnb Places to Stay Under $200

Over 218+ South Shore Varoom and Airbnb Places to Stay Under $200
Merrill From US $75
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Admiral Motel By Oyo Chicago I-94 From US $95
         

3.8 (45 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Bedding/Linens
A Home Away From Home! From US $191
         

9.6 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bright & Cozy 1BR Near UChicago From US $167
         

9.4 (3 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Chic Retreat: Cozy 1BR Apartment From US $165
         

9.0 (6 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Hyde Park Haven | 2BR Retreat From US $186
         

9.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in South Shore

Over 139+ Instantly Bookable Vacation Homes in or Near South Shore
Cozy 3-bedroom condo near University of Chicago From US $275
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
2 Mi to Calumet Park & Beach: Windy City Escape! From US $358
         

2 Mi to South Shore Beach: Urban Retreat w/Yard From US $332
         

Superb townhome with Near Lake in vibrant Chicago From US $223
         

Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago From US $255
         

9.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities
Spacious two bedroom condo with a cozy feel! From US $213
         

8.8 (6 Reviews)
Condo
  • Parking
  • TV
  • Security/Safety

About South Shore Vacation Rentals

With more than 459 South Shore vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel 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 a rental property in South Shore.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel South Shore, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner 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, and other popular Airbnb-style properties in South Shore. Places to stay near South Shore are 499.76 ft² on average, with prices averaging $372 a night.

Bespokeusatravel 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 Rental Accommodation Types in South Shore

Type Count
Holiday Apartments 325
Vacation Homes 82
Hotels with Suites 12
Villas 1

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

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Shore.

Weather in South Shore

View the weather forecast for South Shore before booking your South Shore Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F