Uptown holiday rentals

We found 2,039 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Uptown that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Uptown

Showing deals for:19 June - 26 June

Image gallery for New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

Room
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

Chicago

8% off
Price is AU$26,498
for 7 nights, 1 home
AU$3,785 per night
includes taxes & fees
New, Mega Dream Home in Wicker Park Bucktown - Sleeps 21

Find spaces that suit your style

  • 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

What is the most popular type of holiday home accommodation in Uptown?
Apartments are the most popular style of holiday home in Uptown, according to our data. Even if you've got something a little different in mind, Stayz has holiday homes in all sizes and shapes. Browse our options to find your perfect pad.
How much does it cost to rent a holiday home in Uptown?
Length of stay, property type and season are among the factors that can determine the price of a holiday home. Simply add your dates of travel to find your perfect match. From comfy cabins to expansive luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Uptown?
Prices for beach houses in Uptown will vary depending on the size and style of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and the number of guests to see your home options and prices. From there you can use our filters to refine your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Uptown?
With 26 properties that welcome pets, your furry little friend can join in the fun on your Uptown getaway. Use our filter tool to search our pet-friendly holiday homes and find the pawfect pad on Stayz.
Can I rent a house with a pool in Uptown?
Tick the "pool" box in our filter tool and take your pick of two houses with private pools in Uptown on Stayz. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday property comes with its own pool.
What are popular home amenities in Uptown?
A garden, a nearby waterfront and a lake view top the list of most popular home amenities in Uptown. Whether you plan to travel solo, with your significant other or a group of family members, Stayz will help you find a holiday home that suits your tastes with all the features you're looking for.
Are there large group holiday homes in Uptown?
With three properties that can sleep 10 or more people in Uptown, there's no need to cross anyone off the invite list. From family holidays to special events like weddings and birthday parties, Stayz can help you find a large group home that fits the occasion.
Are there holiday homes in Uptown that welcome kids?
Bring the entire family together for an adventure in Uptown at one of our 26 family-friendly holiday properties. Lots of these stays provide amenities that are perfect for getaways with youngsters, like kitchens, extra bedrooms and outdoor spaces. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Uptown?
There are lots of exciting things to see and do with the family in Uptown, such as:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Uptown?
Uptown has nine one-bedroom homes on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom holiday home is ideal if you're travelling with a friend or your partner. And with home comforts like air conditioning and more privacy than a standard hotel, you'll be able to relax while enjoying this amazing destination.
Can I find two-bedroom holiday homes in Uptown?
Pick from five two-bedroom holiday homes in Uptown. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's space for whoever's fortunate enough to be joining in on the fun.
Are there holiday homes with WiFi in Uptown?
You'll have a choice of 10 holiday homes with WiFi in Uptown. If you want to disconnect from daily life during your trip, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Uptown?
Pick your travel dates and then make use of the filters to find holiday homes with air conditioning in Uptown on Stayz. With 26 air-conditioned properties on offer here, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday home in Uptown?
The minimum required age is usually 16, 18 or 21. It can change across properties on Stayz, so look at the rules of your chosen Uptown stay before making a booking.
How long can I rent a holiday home in Uptown for?
The amount of time you can rent an Uptown holiday home for depends on the property. Just put in your preferred travel dates to view available options that offer long-term stays. They come with all the things you need to make your extended trip more convenient and enjoyable, such as kitchens and yards. Some properties might also offer discounted weekly or monthly prices, so you can stay longer for less money.

More holiday ideas