West Town holiday lettings

We found 1,501 holiday rentals — enter your dates for availability

Discover a selection of 56 homes, 181 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:30 Jan - 6 Feb

Image gallery for Luxury 2BR on Michigan Ave with Private Balcony

Living area
9.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Luxury 2BR on Michigan Ave with Private Balcony

Chicago, IL

7% off
Price is £2,413
for 7 nights, 1 apartment
£345 per night
includes taxes & fees
Luxury 2BR on Michigan Ave with Private Balcony

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    Enjoy full kitchens, pools, gardens and more

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Frequently asked questions

What is the most popular type of holiday rental in West Town?
In West Town, apartments are the most popular type of holiday rental, with approximately 118 available throughout the neighbourhood. These apartments are typically located in vibrant areas close to local attractions, cafes, and shops, offering a convenient base for exploring the city. Most rooms come with fully equipped kitchens, comfortable living areas, and some even feature balconies to enjoy the urban landscape.
Are there any beach house rentals in West Town?
In West Town, Illinois, there are approximately 17 beach house holiday rentals available. These properties are primarily located within vibrant neighbourhoods that provide easy access to local attractions and the scenic waterfront. Most beach houses come equipped with modern amenities, such as fully furnished kitchens, spacious living areas, and outdoor decks or patios, ideal for enjoying the warm weather. Some properties also feature additional luxuries like hot tubs, fire pits, and private gardens, making them superb for families or groups looking for a comfortable and enjoyable stay.
How much does it cost to rent a holiday home in West Town?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in West Town to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for West Town holiday house rentals?
You can find great discounts on house rentals in West Town on Vrbo, 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.
Are there any West Town holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in West Town?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit West Town for a holiday rental?
March is the most popular month to visit West Town, as the vibrant neighbourhood comes alive with a mix of cultural events and outdoor activities. The peak season spans from March to May, attracting travellers eager to explore the area's unique blend of art, dining, and local charm. During this time, visitors can enjoy pleasant spring temperatures, typically ranging from 5 to 15 degrees Celsius, which create a comfortable environment for strolling through the local parks or discovering the eclectic shops and eateries that West Town has to offer.

One of the highlights of visiting in March is the onset of the blooming season, which adds a splash of colour to the streets and enhances the overall experience. This month also features various festivals and markets that showcase local talent, making it a superb opportunity for those seeking vibrant, community-oriented activities.

If you're looking for a more budget-friendly option, consider planning your trip in December. During this time, this month offers a lovely holiday atmosphere with festive decorations and unique local events. The charm of West Town during the winter months, combined with lower accommodation rates, can provide a delightful experience that's both memorable and cost-effective.
Are there any remote work holiday rentals in West Town?
In West Town, Illinois, there are numerous options for remote work holiday rentals, with around 171 properties available. This vibrant neighbourhood is known for its vibrant mix of cafes, shops, and parks, making it an appealing location for those who wish to balance work and leisure. Many of the rentals are equipped with dedicated office spaces, desks, and ergonomic chairs, ensuring a comfortable working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a West Town holiday rental?
Book your West Town holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in West Town?
In West Town, visitors can immerse themselves in a vibrant cultural scene and an array of attractions. The area is known for its artistic vibe, particularly in the Wicker Park section, which boasts trendy boutiques, lively music venues, and a variety of cafes. The historic Humboldt Park offers expansive green spaces and beautiful lagoons, making it a popular spot for outdoor activities and leisurely strolls.
Can I change or cancel my West Town home rental booking on Vrbo?
To find West Town holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the West Town holiday rental prices shown on Vrbo?
Vrbo 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.

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