West Town holiday rentals

We found 1,345 holiday rentals — enter your dates for availability
Discover a selection of 56 homes, 212 apartments and other holiday rentals in West Town that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the amenities that you need and want, including air conditioning and Wi-Fi. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – West Town

Showing deals for:1 Jan - 8 Jan

Interior
River North Luxury Living
The building
French Bistro and Wine Bar - right downstairs
Exceptional
(106 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$5,241
for 7 nights, 1 apartment
AU$749 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Private kitchen
Living area
Living area
Exterior
Excellent
(11 reviews)

Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!

Chicago

8% off
AU$8,004
for 7 nights, 1 home
AU$1,143 per night
includes taxes & fees
Spacious / New - 8BD/4BTH - Sleeps 16 + Garage!
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Bedroom 1 - King Bed
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$9,537
for 7 nights, 1 home
AU$1,362 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Living room area
3 bedroom unit is top floor of historic greystone
Dining room area
View of Robey Hotel from back deck
Exceptional
(100 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$8,272
for 7 nights, 1 home
AU$1,182 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Interior
Room
Terrace/patio
Interior
Exceptional
(75 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
AU$3,409
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Bedroom 3 w/ Queen Bed
Top floor kitchen and dining area
Dining Area
Kitchen on Top Floor
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$8,251
for 7 nights, 1 apartment
AU$1,179 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Front Yard View
Living Room
Patio Deck 2
Bedroom 1 (King Size) + 55Inch TV
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$7,223
for 7 nights, 1 home
AU$1,032 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Fun Mirror Wall Upstairs
Downstairs living area
Kitchen (upstairs)
Upstairs queen bedroom 2
Exceptional
(99 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$14,315
for 7 nights, 1 apartment
AU$2,045 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Living area
Interior
Private kitchen
Exceptional
(14 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

25% off
AU$5,704
for 7 nights, 1 apartment
AU$815 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Interior
Interior
Private kitchen
Room
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$3,020
for 7 nights, 1 apartment
AU$431 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit West Town for a holiday rental?
March is the most popular time to visit West Town, as the city begins to shake off the winter chill and welcomes the vibrant energy of spring. The peak season runs from March to May, making it an ideal period for travellers looking to enjoy outdoor activities, explore local attractions, and immerse themselves in the lively option of the neighbourhood.During this time, temperatures generally range from around 4 to 15 degrees Celsius, creating a comfortable environment for leisurely strolls through the area's parks or enjoying the local café scene. Spring also brings blooming flowers and the return of outdoor events, enhancing the overall experience for visitors who appreciate vibrant urban life.If you're seeking a more budget-friendly option, consider visiting in December. While this is a quieter season, it allows for a unique perspective of West Town, often adorned with festive decorations that create a charming winter atmosphere. Plus, you can enjoy the local dining scene without the usual crowds, giving you a more intimate experience of the neighbourhood.Ultimately, the best time to book a holiday rental in West Town hinges on your preferences—whether you're drawn to the bustling energy of spring or the tranquil charm of winter.
What are the top attractions in West Town, Illinois, United States of America?
In West Town, visitors can immerse themselves in a vibrant mix of culture and creativity. The neighbourhood is home to the renowned Polish Museum of America, which offers insights into Polish heritage and history. Just a short stroll away, the historic Humboldt Park boasts beautiful gardens, a lagoon, and the iconic Humboldt Park Boathouse, superb for a leisurely day outdoors.For those interested in art, West Town features several galleries and studios, particularly along Chicago Avenue, where local artists showcase their work. The area also offers a variety of dining options, from trendy cafes to authentic ethnic restaurants, making it a delightful spot for food enthusiasts. Additionally, the nearby Logan Square neighbourhood provides further attractions, including the popular Logan Square Farmers Market and the vibrant music scene.
Are all fees included in the West Town holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any West Town holiday homes with parking?
Stayz offers a wide selection of holiday homes in West Town with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for West Town holiday homes?
You can find great discounts on holiday homes in West Town on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my West Town holiday home booking on Stayz?
To find West Town holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in West Town?
A long-stay holiday home in West Town is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a West Town holiday home?
Book your West Town holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in West Town?
Prices for holiday homes in West Town vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in West Town to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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