Montrose Beach showing a beach and general coastal views as well as an individual male

Uptown holiday lettings

We found 2,150 holiday rentals — enter your dates for availability

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Dates

Calendar
Flexible dates

July 2025

August 2025

Discover a selection of 5 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:3 Oct - 10 Oct

Exceptional

(18 reviews)

Beautiful Downtown 3BR with Free Parking

Chicago, IL

7% off

£597 per night

includes taxes & fees

Exceptional

(16 reviews)

Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige

Chicago, IL

7% off

£767 per night

includes taxes & fees

Enter into our large 1800 sq. ft. condo, featuring a game room. Perfect for you!

Exceptional

(27 reviews)

City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

Chicago, IL

11% off

£806 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(26 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

£449 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Uptown

Montrose Beach

Find the best place to stay - Uptown

Showing deals for: 1 Oct - 4 Oct

Furniture, Indoors, Living Room, Home Decor, Couch

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 apartment

£282 per night

includes taxes & fees

Home Decor, Living Room, Indoors, Room, Flooring

Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

Sleeps 6 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

£412 per night

includes taxes & fees

Top rated rentals - Uptown

Premier Host

Excellent Place To Stay

Joan, the host, was super responsive, and you can tell works hard to make sure as much as possible is thought of ahead of time. The apartment was clean, and everything in the description was accurate.

Justin M.

Stayed Aug 2020

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, 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 rental accommodation in Uptown?

Apartments are the most popular style of holiday rental in Uptown, according to our data. Even if you've got something a little different in mind, Vrbo 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 rental 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 Vrbo holiday 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 travelling. 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 holiday 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 holiday 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 holiday 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 holiday rental that suits your tastes with all the features you're looking for.

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

Are there holiday rentals 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 rentals in Uptown?

Uptown has nine one-bedroom rentals on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom holiday rental 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 rentals 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 rentals with WiFi in Uptown?

You'll have a choice of 10 holiday 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.

How can I find holiday rentals with air conditioning in Uptown?

Pick your travel dates and then make use of the filters to find holiday rentals with air conditioning in Uptown on Vrbo. 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 rental in Uptown?

The minimum required age is usually 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Uptown stay before making a booking.

How long can I rent a holiday rental 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.