Uptown vacation rentals

We found 2,035 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 7 homes and other vacation rentals in Uptown that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the amenities you expect and more, which might include parking and a hot tub. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of vacation rental accommodation in Uptown?

Apartments are the most popular style of vacation rental in Uptown, according to our data. Even if you've got something a little different in mind, Vrbo has vacation homes in all sizes and shapes. Browse our options to find your perfect pad.

How much does it cost to rent a vacation rental in Uptown?

Length of stay, property type and season are among the factors that can determine the price of a vacation home. Simply add your dates of travel to find your perfect match. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals 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 traveling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to refine your search by ratings, nearby activities and more.

Are there pet-friendly vacation rentals 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 vacation rentals and find the pawfect pad on Vrbo.

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 Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your vacation property comes with its own pool.

What are popular rental amenities in Uptown?

A garden, a nearby waterfront and a lake view top the list of most popular rental amenities in Uptown. Whether you plan to travel solo, with your significant other or a group of family members, Vrbo will help you find a vacation rental that suits your tastes with all the features you're looking for.

Are there large group vacation rentals 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 vacations to special events like weddings and birthday parties, Vrbo can help you find a large group rental that fits the occasion.

Are there vacation rentals in Uptown that welcome kids?

Bring the entire family together for an adventure in Uptown at one of our 26 family-friendly vacation 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 favorite.

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 vacation rentals in Uptown?

Uptown has nine one-bedroom rentals on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom vacation rental is ideal if you're traveling 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 vacation rentals in Uptown?

Pick from five two-bedroom vacation 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 vacation rentals with WiFi in Uptown?

You'll have a choice of 10 vacation rentals 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 Vrbo.

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