Chicago\92s Best Vacation Rentals - Vacation Rentals in West Side
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Luxury Places to Stay in West Side
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Top-Rated Vacation Rentals with a Pool in West Side
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Pet-Friendly Vacation Rentals in West Side
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Large Vacation Homes & Villas in West Side
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Wheelchair Accessible Vacation Homes in West Side
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West Side Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in West Side
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About West Side Vacation Rentals
With more than 1569 West Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals 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 West Side.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals West Side, 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 West Side. Places to stay near West Side are 805.43 ft² on average, with prices averaging US $384 a night.
Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in West Side 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 West Side
| Type | Count |
|---|---|
| Holiday Apartments | 1128 |
| Vacation Homes | 218 |
| Hotels | 68 |
| B&B | 6 |
| Hostels | 5 |
| Villas | 3 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in West Side
★ Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals 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 West Side.
Weather in West Side
View the weather forecast for West Side before booking your West Side Vacation Rentals to confirm your best time to go.
Top Attractions Around West Side, IL
Chicagosbestvacationrentals offers a large selection of top attractions around West Side. Research things to do on your vacation before you visit West Side.
Other Places to Stay Near West Side, IL
Complexes around West Side, IL
West Side Vacation Rental Frequently Asked Questions
What are the top vacation rentals in West Side?
There are a lot of options in West Side. If you plan on staying in the West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in West Side:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- Spacious 4-Level/4-Bedroom Townhouse in West Loop
- Spacious 3/2 Duplex In Wicker Park Area
- Ukrainian Village 3BR/3BA Private Patio, Parking
How many vacation rentals have private pools in West Side?
There are 6 vacation rentals with private pools near West Side. Top-rated homes that have access to a swimming pool include:
Which vacation homes in West Side are best for families?
If you are looking for a family-friendly vacation home in West Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in West Side:
How many vacation rentals are available in West Side?
Currently, the total number of properties listed in 2026 is over 1569 in the West Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in West Side.
