Uptown holiday lettings
We found 2,150 holiday rentals — enter your dates for availability
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
Image gallery for Beautiful Downtown 3BR with Free Parking

9.6 out of 10 rating
Exceptional
(18 reviews)
Beautiful Downtown 3BR with Free Parking
Chicago, IL
7% off
Price is £4,181
£597 per night
includes taxes & fees
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Find the best place to stay - Uptown
Showing deals for: 1 Oct - 4 Oct
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Sleeps 4 · 2 bedrooms · 1 bathroom
10 out of 10
exceptional
(28 reviews)
The current price is £845
for 3 nights, 1 apartment
£282 per night
includes taxes & fees
Top rated rentals - Uptown

Excellent Place To Stay
10 out of 10
exceptional
(47 reviews)
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 mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value