Winters Vacations Rentals - Vacation Rentals in South Shore
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Child Friendly
- Internet
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Security/Safety
Luxury Places to Stay in South Shore
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Pet Friendly
- Designated Smoking Area
Top-Rated Vacation Rentals with a Pool in South Shore
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pet Friendly
- Pool
Pet-Friendly Vacation Rentals in South Shore
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Large Vacation Homes & Villas in South Shore
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
Wheelchair Accessible Vacation Homes in South Shore
- Air Conditioner
- Parking
- View
- Air Conditioner
- View
- Wheelchair Accessible
- Air Conditioner
- Pet Friendly
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pet Friendly
- Pet Friendly
- TV
- Wheelchair Accessible
South Shore Vacation Rentals and Airbnb Places to Stay Under $200
- Air Conditioner
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- Designated Smoking Area
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- Security/Safety
Instantly Bookable Vacation Homes in South Shore
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Designated Smoking Area
- Bedding/Linens
- Air Conditioner
- Parking
- Designated Smoking Area
About South Shore Vacation Rentals
With more than 474 South Shore vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Wintersvacationsrentals 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 Wintersvacationsrentals 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 503.73 ft² on average, with prices averaging US $389 a night.
Wintersvacationsrentals 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 | 332 |
| Vacation Homes | 90 |
| Hotels | 11 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in South Shore
★ Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals 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.
Other Places to Stay Near South Shore, IL
South Shore Vacation Rental Frequently Asked Questions
What are the top vacation rentals in South Shore?
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:
- Modern Apt Near U of Chicago!
- Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
- Come experience The Lake Shore!
- University of Chicago Condo-Upgraded and Spacious w/Parking
- The Brown House - A luxurious UChicago Campus stay
- High-end 2Bdrm Garden Apt. Where Comfort Meets Style
- Lovely three bedroom Loft, University Of Chicago, Obama Library
- A 3-bedroom, 2-bathroom residence that provides ample space and comfort.
- Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
- Cozy & Near Downtown, Hyde Park & the Metra
Which vacation homes in South Shore are best for families?
If you are looking for a family-friendly vacation home in South Shore, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Shore:
How many vacation rentals are available in South Shore?
Currently, the total number of properties listed in 2026 is over 474 in the South Shore area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Shore.
