Cottage Romance - Vacation Rentals in West Side

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12 From US $493
         

Cabin 105 by 747 Lofts From US $244
         

6.4 (13 Reviews)
Hotel
  • Air Conditioner
  • Accessibility
  • Security/Safety

Luxury Places to Stay in West Side

Over 1442+ Luxury Places to Stay in or Near West Side
: The Wolcott : Modern Elegance at Its Finest From US $3,165
         

9.4 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
3 Penthouses, 1 Floor, Group Stay, Sleeps 21 From US $2,204
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Sleeps 18 6BR Gym, Game Room and Theater From US $2,194
         

Prime West Loop 2BR Apts + Event Convenience From US $2,045
         

New
Apartment
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in West Side

Over 238+ Top-Rated Vacation Rentals with a Pool in or Near West Side
Top Floor Views + Central Comfort From US $504
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
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  • Pool
Scenic 3BR PH for Tourism + Prime Location From US $854
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Stylish 2BR Retreat in Fulton Market for Getaways From US $677
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Skyline Views in 3BR Apartment w/Top Amenities From US $1,269
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Deluxe River West PH for Unforgettable Memories From US $718
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
BlueJay/Unique One Bedroom Full of Amazing Art From US $166
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground From US $166
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
iKlektik House/Robin From US $157
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in West Side

Over 594+ Pet-Friendly Vacation Rentals in or Near West Side
NEW LUXURY PENTHOUSE CONDO From US $422
         

10.0 (202 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Chicago Quick Stay From US $130
         

6.3 (47 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Internet
Art Villa From US $1,030
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • View
NEW LUXURY CONDO WITH PATIO DECK From US $284
         

10.0 (191 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Prime Location! Modern 3 Bed 3 Bath Rental in Chicago From US $457
         

10.0 (32 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Wicker Park Entire House, Private Yard and Parking From US $1,902
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
West Loop Living – Bright 1BR From US $168
         

10.0 (7 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Large Vacation Homes & Villas in West Side

Over 201+ Large Vacation Homes & Villas in or Near West Side
Homan Square From US $7
         

3.0 (193 Reviews)
House
  • Parking
  • Child Friendly
  • Internet
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
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  • Parking
  • Pet Friendly
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $953
         

Modern West Loop Gem-City Views & Prime Location 6 From US $370
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Modern West Loop Gem-City Views & Prime Location 4 From US $764
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern West Loop Gem-City Views & Prime Location 3 From US $688
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
2 Suites, 2 Floors in Downtown Chicago From US $493
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in West Side

Over 444+ Wheelchair Accessible Vacation Homes in or Near West Side
City Views + Walk to Dining, Ideal for All From US $523
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern River West 2BR with W&D by Zencity From US $77
         

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10.0 (1 Review)
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  • Parking
  • Wheelchair Accessible
The Publishing House B&B From US $206
         

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9.8 (195 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
1 Garage Parking/Skyline Rooftop/PingPong/Balcony From US $308
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Unique Luxury Fulton Market Penthouse - Sleeps 32 From US $1,749
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
High-End West Loop 2BR + City Views & Walkability From US $548
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Panoramic City Views + Prime West Loop Location From US $492
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Balcony, 1 Garage Parking, Sleeps 8! From US $321
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV

West Side Varoom and Airbnb Places to Stay Under $200

Over 643+ West Side Varoom and Airbnb Places to Stay Under $200
Spacious & private! Free parking! Great location! From US $197
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern River West 2BR with W&D by Zencity From US $76
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Internet
Chicago Parthenon Hostel From US $114
         

8.2 (449 Reviews)
Hostel
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Spacious loft in the heart of West Town, Noble Square Chicago From US $159
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
King Comfort apartment, Quiet, Clean, AC & WiFi From US $107
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in West Side

Over 798+ Instantly Bookable Vacation Homes in or Near West Side
3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $264
         

1F Chicago's Little italy Graystone nearDowntown From US $284
         

10.0 (169 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private Historic Coach House Wicker Park From US $332
         

10.0 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Entire Below Level Studio w/Private Sauna From US $221
         

10.0 (65 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About West Side Vacation Rentals

With more than 2 West Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cottageromance 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 Cottageromance 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 850 ft² on average, with prices averaging $369 a night.

Cottageromance 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
Hotels with Suites 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in West Side

Pro Tip: Cottageromance makes it easy to compare the best listings on Cottageromance homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cottageromance 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.

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