Owner Direct Vacation
Rentals in Uptown
The Best Owner Direct Vacation Rentals in Uptown. Explore thousands of vacation home rentals, large cabins, and villas near Uptown
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Explore the Best Uptown Vacation Homes
Looking for the perfect place to stay in Uptown? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Uptown character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Uptown Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Uptown
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Popular Neighborhoods for Uptown Vacation Rentals
What are the best areas to stay in Uptown
Discover the top neighborhoods in Uptown and choose a place that suits your stay.
Friday Feb 13
Uptown, Chicago
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Uptown vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Uptown
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How to Reserve Your Uptown Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Uptown Vacation Rental FAQs
1. What are the top vacation rentals in Uptown?
There are a lot of options in Uptown. If you plan on staying in the Uptown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Uptown:
- Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- ❤️ Spacious and Airy Apartment With Parking On Site!
- Spacious 2-BR Condo + Free On-Site Parking
- Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
- Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Uptown Gem
- Chic apartment in marvelous Chicago with WiFi, AC
- Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
- -Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
2. Which vacation homes in Uptown are best for families?
If you are looking for a family-friendly vacation home in Uptown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Uptown:
3. How many vacation rentals are available in Uptown?
Currently, the total number of properties listed in 2026 is over 87 in the Uptown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Uptown.