- USA
- Illinois
- Chicago
- Near West Side
- Winter Rental
Near West Side Winter Rentals & Holiday Homes
Discover winter rentals Near West Side - We found 83 exact matches
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
About Near West Side Winter Rental on SunSkiResorts
Planning a winter vacation in Near West Side? Discover 83 places to stay, ideal for families, friends, groups, or wedding retreats.
At SunSkiResorts, explore a wide array of accommodations in Near West Side, IL perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Winter accommodations in Near West Side start at US $413. The most popular properties in Near West Side include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.
To book your winter vacation homes in Near West Side, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Near West Side and unlock incredible deals.
Frequently Asked Questions About Near West Side Winter Rentals
There are a lot of options in Near West Side. If you plan on staying in the Near West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Near West Side:
- 1F Chicago's Little italy Graystone nearDowntown
- Top Floor Views + Central Comfort
- Sunlit Room+Bath in Chicago Condo near United Center, West Loop, & Med District
- Stylish 2BR Retreat in Fulton Market for Getaways
- Relaxing Studio with Private Patio Downtown Chicago
- Charming Cottage Home Near Little Italy & UIC
- Skyline Views in 3BR Apartment w/Top Amenities
- Luxury West Loop Rentals: Modern Suites w/City Views & Resort Amenities
- The Banksy-King Bed-Firepit-Rooftop-United Center
- Quick Drive to Downtown Chicago & Early Check-In
- Charming 2-bedroom 2-bathroom apartment near Downtown Chicago
- Fulbrix Bright Designer Apartments with West Loop Views
- Hampton Inn Chicago West Loop Fulton Market Area
- Top Floor Views + Central Comfort
See all pet-friendly vacation rentals in Near West Side on SunSkiResorts
About 83 holiday rentals in Near West Side boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
