West Town holiday lettings
We found 1,340 holiday rentals — enter your dates for availability
Discover a selection of 59 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:25 Dec - 1 Jan
Exceptional
(13 reviews)
6BD/5BTH + Roofdeck - Downtown Chicago!
Chicago
£11,425
for 7 nights, 1 apartment
£1,632 per night
includes taxes & fees
Exceptional
(91 reviews)
Historic luxury townhouse on Chicago's Gold Coast
Chicago
£9,989
for 7 nights, 1 home
£1,427 per night
includes taxes & fees
Exceptional
(8 reviews)
5BR/4BA Modern SFH Logan Square!
Chicago
£3,231
for 7 nights, 1 home
£462 per night
includes taxes & fees
Exceptional
(34 reviews)
The Exclusive- 7 Bed, 6 Bath Retreat
Chicago
£5,838
for 7 nights, 1 apartment
£834 per night
includes taxes & fees
Exceptional
(92 reviews)
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Chicago
£5,774
for 7 nights, 1 home
£825 per night
includes taxes & fees
Exceptional
(23 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago
£5,182
for 7 nights, 1 home
£740 per night
includes taxes & fees
Exceptional
(100 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
£3,576
for 7 nights, 1 home
£511 per night
includes taxes & fees
Exceptional
(99 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
£7,321
for 7 nights, 1 apartment
£1,046 per night
includes taxes & fees
Exceptional
(12 reviews)
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Chicago
£1,616
for 7 nights, 1 apartment
£231 per night
includes taxes & fees
Exceptional
(6 reviews)
Peaceful Zen Flat | 2BR Oasis with Free Parking
Chicago
£2,232
for 7 nights, 1 apartment
£319 per night
includes taxes & fees
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Find properties near top attractions in West Town
Find the best place to stay - West Town
Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 29-Oct 2
Sleeps 5 · 2 bedrooms · 1 bathroom
The Neighborhood Hotel-Little Italy
Sleeps 3 · 1 bedroom
Wicker Park near Downtown & Salt Shed Sept 30-Oct 2 Last Minute Deal 115.00
Sleeps 5 · 2 bedrooms · 1 bathroom
Level Chicago – Old Town
Sleeps 4 · 1 bedroom · 1 bathroom
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12
Sleeps 12 · 3 bedrooms · 2+ bathrooms
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Sleeps 10 · 4 bedrooms · 3 bathrooms
Top rated rentals - West Town
Great option!!!!
We had a lovely stay! Amenities were next level! Lots in area to access as well! Perfect in every regard!
Kara
Stayed Aug 2024
An amazing place from which to explore Chicago
Had an amazing stay, the Sentral staff, all the staff, were so friendly and welcoming. For example, Augustine sorted out an issue with a missing fob so very quickly and easily.
The property itself is amazing. We went for one of the upgraded apartments and were lucky enough to get one on the 18th floor with views covering the city and the park (so we could look one way and see the Willis Tower in one direction and the lake and Museum district in the other. The sunrises over the lake were particularly spectacular. The apartment was fitted out exactly as the online walk though tour shows it and it was a pleasure to come back to after exploring the city each day. The shared facilities on the 7th floor were great - we only really used the Winter garden and the out door hot tub - from which you can also watch the sunrise.
Being in the South loop and right on the edge of the park district it is really well positioned to act as a base to explore Chicago - there was a Divvy bike rack (where you can rent bikes to explore the area - with many more dotted around so you can stop / start easily) within a couple hundred meters of the apartment block. With it being within walking distance of all the CityPass attractions (which lets you visit Chicago places of interest at a significant saving) it was perfect.
Richard
Stayed Nov 2022
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
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 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.
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, 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.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.
Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.
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