Rent The Cottages - Vacation Rentals in West Side

3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $271
         

Homan Square From US $7
         

3.0 (193 Reviews)
House
  • Parking
  • Child Friendly
  • Internet
The Publishing House B&B From US $217
         

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9.8 (188 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible
NEW LUXURY PENTHOUSE CONDO From US $399
         

10.0 (200 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW LUXURY CONDO WITH PATIO DECK From US $293
         

10.0 (190 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in West Side

Over 1404+ Luxury Places to Stay in or Near West Side
6 Luxe Apts, Perfect Group Solution, Sleeps 30 From US $3,767
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
: The Wolcott : Modern Elegance at Its Finest From US $3,480
         

Exclusive Group Getaway in Vibrant West Loop From US $3,433
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sleeps 18 6BR Gym, Game Room and Theater From US $2,194
         

Ruby Room From US $1,996
         

8.1 (53 Reviews)
Hotel
  • Air Conditioner
  • View
  • Balcony/Terrace
Wicker Park Entire House, Private Yard and Parking From US $1,902
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • 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 $459
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Scenic 3BR PH for Tourism + Prime Location From US $559
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Relaxing Studio with Private Patio Downtown Chicago From US $507
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish 2BR Retreat in Fulton Market for Getaways From US $485
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Skyline View Duo for Groups: Unmatched Luxury Stay From US $1,262
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury West Loop Rentals: Modern Suites w/City Views & Resort Amenities From US $793
         

Skyline Views in 3BR Apartment w/Top Amenities From US $732
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in West Side

Over 586+ Pet-Friendly Vacation Rentals in or Near West Side
Prime Location! Modern 3 Bed 3 Bath Rental in Chicago From US $411
         

10.0 (31 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
Stylish 1BR in West Loop From US $180
         

10.0 (10 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Cozy Boho Chicago - 10 Minutes to Downtown Chicago From US $204
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 4BR Near Wicker Park From US $314
         

10.0 (6 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety
Updated Designer Duplex In Fulton Market W/parking From US $656
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in West Side

Over 205+ Large Vacation Homes & Villas in or Near West Side
NEW! Spacious Art Deco Modern 5 BD/3BA Condo From US $580
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 4-Level/4-Bedroom Townhouse in West Loop From US $935
         

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym From US $516
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
2 Suites, 2 Floors in Downtown Chicago From US $879
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern West Loop Gem-City Views & Prime Location 6 From US $276
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Designer Apt, Billiards, Private Patio, 1 Parking From US $436
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in West Side

Over 444+ Wheelchair Accessible Vacation Homes in or Near West Side
Modern West Loop Gem-City Views & Prime Location 4 From US $360
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Modern River West 2BR with W&D by Zencity From US $77
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Cabin 105 by 747 Lofts From US $150
         

10.0 (1 Review)
Apartment
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
1 Garage Parking/Skyline Rooftop/PingPong/Balcony From US $308
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern West Loop Gem-City Views & Prime Location 2 From US $261
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Unique Luxury Fulton Market Penthouse - Sleeps 32 From US $1,745
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
High-End West Loop 2BR + City Views & Walkability From US $418
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
City Views + Walk to Dining, Ideal for All From US $398
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

West Side Varoom and Airbnb Places to Stay Under $200

Over 654+ West Side Varoom and Airbnb Places to Stay Under $200
Spacious & private! Free parking! Great location! From US $147
         

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 $139
         

8.2 (441 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
Flexhome Ukrainian Village 2BR D1 From US $189
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in West Side

Over 770+ Instantly Bookable Vacation Homes in or Near West Side
Private Historic Coach House Wicker Park From US $318
         

10.0 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Entire Below Level Studio w/Private Sauna From US $200
         

10.0 (61 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Trendy West Town Flat - 2 bed/1.5 bath with parking From US $273
         

Luxury Modern home minutes from Downtown Chicago From US $469
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bucktown Private Condo From US $313
         

10.0 (14 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace

About West Side Vacation Rentals

With more than 1413 West Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rentthecottages 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 Rentthecottages 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 783.79 ft² on average, with prices averaging $334 a night.

Rentthecottages 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 1018
Vacation Homes 203
Hotels with Suites 53
B&B 5
Hostels 3
Others 1
Villas 1

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

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