82+ Vacation Rentals & Holiday Homes in Uptown |
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Uptown Accommodations - Hotels & Rentals

About Uptown Vacation Rentals

Discover More than 82 Incredible Getaway Rentals Available in Uptown. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Uptown.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Uptown, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Uptown. The Average Size of Places to Stay Near Uptown is 574.85 ft², with Prices Averaging US $277 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Uptown. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Uptown

Type Count
Holiday Apartments 60
Vacation Homes 11

Use these Quick Filters to Find a Vacation Rental in Uptown

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Uptown with Online Reservations.

Weather in Uptown, IL

View the weather forecast for Uptown before booking your Uptown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Graceland Cemetery 1,163 Properties
Our Lady of Lourdes Church 1,122 Properties
Sheridan Park 1,113 Properties
About Face Theater 1,095 Properties
Buena Park 1,094 Properties
Essanay Studios 1,092 Properties
Pegasus Players 1,090 Properties
Riviera Theatre 1,081 Properties
Methodist Hospital of Chicago 1,077 Properties
Hutchinson Street District 1,069 Properties
Aragon Entertainment Center 1,066 Properties
Aragon Ballroom 1,066 Properties

Frequently Asked Questions About Uptown?

What are the top hotels, lake houses & vacation rentals in Uptown?

We provide an array of great vacation destinations in Uptown. If you are looking to stay in or around the Uptown area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Uptown:

Which hotel, lake house, or vacation rental in Uptown is best for families?

Searching for a family-friendly getaway in Uptown? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Uptown?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 82 in the Uptown area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Uptown.

Nearby Neighborhood (8) 
Neighborhood Property Count
Lakeview Vacation Rentals in Chicago, Illinois 234
Edgewater Vacation Rentals in Chicago, Illinois 55
Ravenswood Vacation Rentals in Chicago, Illinois 29
Edgewater Beach Vacation Rentals in Chicago, Illinois 734
Andersonville Vacation Rentals in Chicago, Illinois 978
Buena Park Vacation Rentals in Chicago, Illinois 1094
Lakewood-Balmoral Vacation Rentals in Chicago, Illinois 975
Sheridan Park Vacation Rentals in Chicago, Illinois 1113

People Also Ask

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